The pavement in California holds heat differently on a summer night.

Thinking back, I can still smell the oil of the asphalted urban jungle.

I’m 24—barely a decade ago—sleeping at the Maidu skate park in Roseville.

I had figured out that if you lay flat on the asphalt around 11 PM, you could feel the day still radiating up through your back.

Oddly relaxing; nostalgic.

I had a BMW parked a block away that I couldn’t afford and couldn’t sell without going further upside down on the loan. I was trading Magic cards to 12-year-olds for L&L BBQ and Little Caesars $5 pizza on Sunrise boulevard.

And I remember looking up at the stars thinking—how nice is this? How lucky am I?

That sentence has stayed with me. Not because it was profound. But because it was true.

I had absolutely nothing and absolutely everything at the same time. I had perspective.

If this is the worst it gets, why am I so afraid to live?

I had decided the answer was that I shouldn’t live, just a few days earlier.

I even had a plan.

I was standing on the railing of the Foresthill Bridge, 30 minutes north.

I had been there a while. I don’t remember most of what I was thinking—I remember the kind of quiet that arrives when you’ve stopped negotiating with yourself.

Someone drove by and shouted “Jump, pussy.”

Gee. Thanks.

And it snapped me out of the trance.

I gasped for a breath—and my heart pumped ice through my veins.

I climbed down. I drove back to Roseville shaken to the core.

A few nights later I was in the skate park, looking at stars, feeling the heat come up through my back, asking the wrong question of myself for the first time in years.

Not “Why should I keep going.”

“Why am I so afraid to live?”

What I Was Supposed to Be

I am the child of rape.

My mother was 20, in Narcotics Anonymous trying to get clean from heroin, when she was assaulted.

She kept me.

I didn’t know any of this until I was almost 30. Perhaps ignorance really is bliss.

The man who raised me, who I will forever call my father, came into my mother’s life when she was seven months pregnant and chose this.

He was 20.

When I was 20, I could barely do my own laundry.

By many measures, I was not supposed to be here at all.

There are entire forums on the internet dedicated to arguing that pregnancies like the one that produced me should be ended early.

I am the poster child for that argument.

It is a strange thing to reconcile with the life I have today.

That was just the beginning.

I grew up inside substance abuse and domestic violence.

The house I came home to was not safe.

I learned early to read tone, footsteps, the angle of a jaw, the ounces remaining in a fifth of hard liquor or how many spilled rings of Bacardi hung around the base of a shot glass.

You know—all the small signals that tell a kid how the next hour is going to be.

I made myself small.

I quieted my footsteps in the hallways of my own house.

I still do.

Grown ass man, six-three, walking through my own home in Montana with nothing to fear—but I catch myself stepping softly through my house to avoid alerting the demons.

Some things you don’t unlearn. You just notice about yourself.

By other measures, I was not supposed to make it past the bridge.

And I am not even the worst case in my own house.

My wife Mary’s predetermined outcome was worse than mine.

She was the youngest of five girls raised in a single trailer in the woods, born to meth-addicted parents—five girls to multiple fathers, the kind of household that has a script for how it ends.

Her mother found out she was pregnant with Mary during a car accident, four and a half months along, high on meth.

Mary refused to read the script. It’s one of the countless things I adore about her.

When I met her, she had more clarity about what her life was going to be than I have ever had about anything.

She learned from the mistakes of others. She refused to be a victim—coming from a world where success looked like not getting pregnant at 12.

She is the one who taught me what self-agency looked like, because she had it before I knew it was an option.

In ‘23 our first son Noah was born with cystic fibrosis.

Less than a decade ago, his life expectancy was under 7 years.

The medical literature said don’t bother.

By the time he was born, gene modulators like Trikafta had changed the math so completely that he will likely never experience symptoms and has a full life expectancy.

The Cystic Fibrosis Foundation funded the research that made that true. The Cody Dieruf Foundation, here in Montana, makes sure families in the Northern Rockies—hours from any specialized care—can actually access it.

I will spend the rest of my life paying both of them back.

Our second son Nathan was born premature and spent weeks in the NICU, his lungs fighting to do what lungs are supposed to do. It didn’t look good.

Let’s just say, his lungs are working damn good now as testament to his 4am escapades.

The question I have been carrying since the skate park, and the question this newsletter has been circling for over a year—and the question my forthcoming book is named after:

What is predetermined in your life?

What I Got Wrong About It

For most of my life, I thought the answer was most things.

I thought the way you were born determined how the world treated you. I thought the situations you got placed in defined the ceiling. I thought job descriptions were laws of physics. I thought salary bands were real.

I thought authority—the kind that came from titles and credentials and gray hair and pedigree and money—was something other people had access to and I didn’t.

I was wrong about almost all of it. I learned that it could be manufactured.

Cialdini would approve.

The disadvantages are real. I am not pretending otherwise.

Mary and I spend a lot of time talking about how to engineer adversity into our kids’ lives precisely because we know what its absence does. Jeesh, what an incredibly privileged thing to say.

Unfairness is real. The systems built to write your future before you walk into the room are real.

What I got wrong was assuming the story was finished.

I started applying for jobs that required credentials I didn’t have. I got some of them. I started naming my own number instead of accepting what was offered.

The offers changed. They got bigger.

I started telling people what to think about me before they could fill in the blanks themselves.

They thought what I told them to think.

To be honest, most of what I did—didn’t work.

For every job I got that I had no business getting, there were hundreds of rejections I deserved and a few I probably didn’t. I applied to a thousand jobs in a day—when easy apply was truly easy.

I must have got nine hundred and ninety something nos. The other few became something I could learn from.

My rejection ratio never really improved.

The thing I had going for me wasn’t talent. It wasn’t credentials. It wasn’t even the chip on my shoulder, though that helped.

It was that none of the rejections compared to the house I’d come from. None of them compared to the bridge.

So when someone told me no, I laughed.

What were they going to do—make me feel small? M’kay.

Make me feel scared? Try harder.

I never cared much for the people telling me no. So I didn’t care much about what they had to say.

Rather, I focused on finding the few who did.

None of this was magic. None of it was easy.

Most of it took breakthroughs I cannot fully explain, lucky breaks I did not deserve, and the kind of grinding unglamorous work that is invisible to everyone except the person doing it.

Mary’s belief in me did most of the heavy lifting—all granted through God’s grace.

So did the strangers who, for reasons I still don’t understand, decided to give a young kid with a chip on his shoulder and no degree a chance at jobs that should have gone to someone with three.

Ignoring “the rules” started working for me.

But if I could have you as the reader understand one thing from every article I’ve ever published in this newsletter it’s that:

The predetermined story is the story you accept. Not the story that’s true.

The Cost of Refusing

From 2016 to 2021, I had built a company called Discover Podium to a few million in ARR.

Twenty-five employees. A thousand clients a year.

The kind of momentum that gets you on lists.

We helped executives find work at companies like Google, Apple, Cisco, and the hundreds of mid-market tech companies that were hiring like crazy in the late 2010s.

I had no business running a company at all, let alone one that was working.

Then COVID hit.

By April of 2020, I had spent a month on the phone with my employees and their spouses, telling them I would do everything in my power to keep their family employed through whatever this was about to become.

• Some of them had just had babies.

• Some were caring for elderly parents.

• All of them had trusted me when I made that call.

I spent countless hours on the phone negotiating with former satisfied clients that had disputed their charges on services rendered over 12 months prior in economic panic.

Losing the funds for your payroll while accounts are in dispute for 90 days is maddening, I tell ya.

We weathered the storm and bounced back stronger.

Later in the year, I got an offer to sell the business for several million dollars.

The condition was that I had to fire my team.

I said no.

Then I went into personal debt and unwound the company over the course of a year.

I took the PPP loans the government issued and gave every dollar of them to my staff—paid them probably too generously, structured it like severance, pointed half my sales team’s bandwidth at finding placements for the other half.

By the end, the business was worth nothing.

The thing that could have made me wealthy was gone.

I moved my family to a 1,200-square-foot house in Montana with the last $10,000 I had to my name. Gained 100 pounds in sadness over the next year—and sat with whether any of it had been worth it.

I tell that story not because it was virtuous.

I tell it because predetermined-refusal isn’t a feel-good slogan.

It is a discipline that costs you things. It’s real life.

The predetermined good outcome was right there. Sell the company. Take the money. Move on. Everyone would have understood. My advisors actively wanted me to.

My soul did not.

The people I was trying to protect would have been laid off three months later anyway when the buyer restructured—that’s how those deals always end.

Refusing it cost me a number I still don’t entirely want to think about.

Most of the people I protected don’t remember me. A few of them probably still think I was the toxic CEO who couldn’t keep the company alive. The math doesn’t reconcile. It still doesn’t.

That was the trade. I would make it again.

The point isn’t that I made the right call.

Reasonable people would have made the other one and slept fine. The point is that the call existed at all—and that the predetermined script for that moment was so loud, so obvious, so endorsed by everyone around me, that I almost couldn’t hear myself thinking otherwise.

That’s the cost of treating other people’s voices as your predetermined decision.

It doesn’t tell you the wrong answer.

It removes the question. It destroys your curiosity—no matter how naive it seems in challenging it.

Where the Thesis Lives Now

Everything I just told you about my own life applies to your career.

Not as metaphor. As mechanism.

If you are reading this as an executive, here is what predetermined means for you:

Your last comp number is not your next one. The ceiling you were told exists doesn’t.

• The salary band is a compliance filter, not a law of physics.

• The recruiter who told you the budget is fixed is repeating a script that was written before they were hired.

• The room you are in right now is not the only room.

• The people deciding your future are not deciding it with information you don’t also have access to.

• The story you have been told about what kind of trajectory is realistic for someone like you was written by people who needed you to believe it.

Most of them don’t even know they were writing it.

The script is institutional. Nobody is twirling a mustache.

The HR business partner who told you the comp band caps at $X genuinely believes the comp band caps at $X. The recruiter who said we don’t have flexibility on equity genuinely believes there is no flexibility on equity.

They are not lying to you. They are repeating what was repeated to them.

That is what makes it dangerous.

The script doesn’t need a villain to keep working. It just needs everyone in the room to stop questioning it.

Your job is to question it.

If you are reading this as a CHRO, a board comp committee member, or someone who designs the systems on the other side of the table, here is what predetermined means for you:

The compensation architecture you inherited is telling your best people their futures are predetermined.

The bands. The merit cycles. The succession plans.

The we don’t make exceptions for individual contributors at that level.

All of it is a story your organization is telling about what people are worth—and your sharpest leaders are starting to notice the gap between the story and the math.

You are losing the people you cannot afford to lose because they figured out the script before you did. The fix is not better retention bonuses. The fix is honest architecture.

It’s about value-expansion through alignment not slice-carving through adversarial positions.

The most expensive talent decision your company makes this year will not be the one you flag as a comp decision. It will be the one your most valuable VP makes quietly at her kitchen table on a Tuesday night when she finally lets herself ask the question her boss has spent two years training her not to ask:

What if none of this was actually predetermined?

That question, asked one time, is worth more than any retention package you will ever write.

What’s Coming

I have been quiet about most of this until now. The readers who have been showing up here every Thursday for several years deserve to know what they have been part of building.

The book is real.

Predetermined: Rewrite The Rules To Command Your Life is in active development with a Q3 2027 launch.

Publisher conversations are underway. The manuscript is being shaped from the same material that has been showing up in these articles—the frameworks, the client stories, the thesis that became the title.

A preorder waitlist is opening soon.

It serves from survival all the way through self-actualization.

A portion of every book sold will go to the Cody Dieruf Foundation. If this thesis means anything, it means making sure other families don’t have to figure out how to fight a rare disease alone in the Northern Rockies.

That is the version of not predetermined I care about most.

The podcast is coming.

I am building a show about leaders who have overcome predetermined circumstances—the people whose statistical outcomes said one thing and whose actual lives said another. Different stories than mine. Bigger stories than mine. The conversations I wish I had been able to find when I needed them most.

More on the format and the first guests soon. The show will live alongside this newsletter, not replace it.

This newsletter has made all of it possible.

Every share. Every comment. Every reply. Every person who forwarded an article to a friend who needed it. Every reader who became a paid subscriber not because they needed the perks but because they wanted to bet on the work.

You are the reason any of this gets to exist.

The “Why I Finally Called It Quits With LinkedIn” piece reached more people than I knew how to reach on my own.

You did that. Not me. Not the algorithm I had just deleted.

You.

I do not take that lightly.

PS—quitting LinkedIn gave me enough time back to average 15,000+ steps a day and lose all of those 100 pounds back—good riddance LinkedIn!

One thing I would love your help on.

If you want on the preorder waitlist when it opens, drop the word PREDETERMINED in the comments below.

I will make sure you are first in line when the doors open, and first to know about the podcast launch, the early chapter reads, and anything else that comes from this body of work in the months ahead.

This is the part of the work I cannot do alone.

The Conversation

Nils Vinje asked me on his podcast what I think is actually predetermined for us in life.

We talked for 90 minutes. It is the most I have ever said out loud about any of this—the skate park, the biological father, the company shutdown, and the question I have been carrying for the last decade plus.

If the article was the thesis, the podcast is the evidence.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

The compliment I hear most often from clients isn’t about the money.

It’s this:

“Man, I wish I’d known about you twenty years ago.”

I nod. I smile. I say something gracious.

And I think to myself—what if you had?

What if I had?

What if someone had sat 16-year-old me down and said here’s the one thing you need to know before you walk into any room for the rest of your life.

Not a framework. Not a tactic. Not a seven-step playbook.

One idea. Small enough to fit in a kid’s head. Big enough to change a life.

I’ve spent fifteen years negotiating executive contracts against some of the most sophisticated compensation teams in the world. Over a billion dollars in outcomes. Thousands of engagements.

And when I strip all of it back—every tactic, every framework, every piece of IP I’ve built—it all sits on top of a single idea I didn’t learn until I was almost 30.

Here it is.

Most of what you think are rules are just habits other people got tired of questioning.

That’s it.

• The salary band is a habit.

• The job description is a habit.

• The “we don’t make exceptions” is a habit.

• The seven rounds of interviews.

• The merit cycle.

• The comp band.

• The hierarchy.

• The way meetings work.

• The way promotions work.

• The way somebody decides what you’re worth.

All of it was written by people who are no longer in the room.

Most of the people enforcing those rules today can’t tell you who wrote them, when, or why. They’re repeating what was repeated to them.

Nobody is lying. Nobody is being malicious.

The system just keeps running because nobody thought to press pause and ask whether the rules still make sense.

That’s not a conspiracy. That’s just how institutions work.

And once you see it, you can’t unsee it.

What This Looks Like in Real Life

I had a client last year—brilliant operator, first-generation career professional, terrified of asking for more than what the recruiter offered.

Her mother raised her to be grateful. Her father raised her to work hard.

Both of them raised her on rules they learned from their parents—rules built for a labor market that no longer exists.

She walked into the negotiation believing the offer was the offer.

We added $340,000 in year-one comp and a severance provision her recruiter told her wasn’t possible.

The company agreed to all of it in under 72 hours.

Nothing had changed on their end.

They hadn’t suddenly gotten more budget. The “no flexibility” wasn’t a fact—it was a habit. A script the recruiter had been trained to recite because most candidates stop asking the moment they hear it.

My client didn’t stop asking.

That’s the whole difference.

The Version I’d Give a Kid

Here’s how I’d say it to my 16-year-old self. Or to yours. Or to Noah and Nathan when they’re old enough to hear it.

Most of the rules you’re going to run into in your life were written by somebody else for somebody else a long time ago.

Some of them are real. Gravity is real. Kindness is real. The consequences of lying are real.

Many of them aren’t.

Question everything.

Many of them are just the path of least resistance—the version of reality that’s easiest for everyone to agree on because questioning it would take work.

Spoiler alert: You’re allowed to question it—and in some cases, you’ll be rewarded for it in an outsized manner.

And finding success doing so—especially over and over again—is highly addictive.

You’re allowed to ask why does it work this way? out loud. You’re allowed to ask who decided that? and when? and what happens if I don’t?

You’re allowed to look at the rule. Look at the person enforcing it. Look at the cost of breaking it. And make your own decision.

That is the whole skill.

Not confidence. Not charisma. Not some special gift.

Just the willingness to ask one more question after everyone else has stopped.

Why Nobody Teaches This

Because it’s dangerous.

Not to you—to the system.

If every kid grew up knowing that most rules were negotiable, institutions would have to work a lot harder to enforce them.

• Schools would have to explain why the bell rings every 47 minutes.

• Companies would have to explain why the raise is capped at 4%.

• Governments would have to explain a lot of things they’d rather not.

So the skill gets buried. Not maliciously. Just by default.

The kids who learn it usually learn it by accident—from a weird uncle, a rebellious friend, a book nobody assigned them, or a hard-enough life that following the rules stopped feeling like an option.

I learned it the hard way. Most of my clients learned it the hard way. Almost nobody learns it on purpose.

That’s what I’m trying to fix.

My Ask

If you have kids, tell them.

But maybe tell them to questions others and not simply defy your parental authority. Spoken from my experience raising a one year old and three-nager.

Not when they’re 25 and already mid-career and wondering why their salary hasn’t moved in four years. Tell them now. Tell them at 10. Tell them at 14. Tell them at 22 before the first offer letter shows up.

Most of what you think are rules are just habits.

You’re allowed to ask why.

You’re allowed to ask what if.

You’re allowed to walk in and build a life that looks nothing like the one the script had in mind for you.

That single sentence, delivered at the right age, is worth more than any MBA, any network, any inheritance.

It’s the thing this entire body of work is built on.

And next week, I’m going to tell you where it came from — and what it cost me to learn.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

I need to tell you something that might be uncomfortable.

I represent the executives you’re trying to hire.

SVP through C-suite.

F500. Tech. Healthcare. Financial services. PE portfolio companies.

For fifteen years, I’ve sat across the table from your recruiters, your comp committees, your investor talent scouts, your CHROs, and your boards—advocating for the candidates you spent months courting.

All the while being fingerprintless.

I know what they say about your offers. Not what they tell your recruiters or hiring managers.

What they tell me. What they’re too kind to tell you.

And what I’m hearing—across thousands of engagements—is that the money is often wrong. Anchored to a midpoint. Calibrated to last year’s market. Read by the executive as a lowball before they finish the first page.

However, I’m sure you expected that. Everyone wants more.

What I find more interesting is that the compensation structure and alignment is what’s often most wrong.

Your offers look like you don’t believe in the person you’re hiring.

They look exactly like what everyone else is putting in front of them.

You demand transformational results—yet you don’t offer transformational compensation.

I get it. I’ve been a CEO.

One thing before we start. I'm not the boogeyman.

I know I'm often treated like one—the guy on the other side who's coming to take a pound of flesh out of your offer.

That's not what I do.

I don’t do deals where the company loses. The companies always win.

The companies that work with executives I represent end up with better-aligned leaders, clearer expectations, and structures that pay for themselves in the first year. Because we put in the work.

We’re not here to shrink your pie. We’re here to show you where the pie is bigger than you thought—and how to capture it for both sides.

Everyone thinks they’re top talent. Most aren’t. Some are lying to you.

Most are lying to themselves.

You don’t want to absorb the risk of someone who can talk the talk but can’t walk the walk.

But the problem is what your compensation structure tells high-performance leaders about how you see them.

A flat benchmark offer—base, target bonus, four-year vest—tells an A-player you’re buying a seat-filler.

That your comp design was built to manage cost, not attract conviction. That your system is optimized for the average hire, not the transformational one.

The best executives notice when a company has put thought into the deal. They notice when it has simply copied the band. Pay data is everywhere now—they’ve already guessed at your range before they walked in.

And they know when they’re being lowballed.

They go from excited to deflated. Yes, that same person you spent months convincing to take the call.

They read your offer as evidence of organizational maturity—and they self-select toward the companies that signal confidence and away from the ones that signal caution.

These leaders are watching big deals land all around them—they have networks that talk too. Expectations have moved. If your offer hasn’t, you’re not competitive—you’re nostalgic.

But this isn't about the people on the other side of your table.

It's about the architecture of the table itself—and how the companies that redesign it are the ones winning the leaders everyone else is losing.

This is the first piece I’ve ever written for companies and those managing compensation committees.

Sixty-two articles in this publication have been for the executive.

How to negotiate. How to see the system. How to build a career that compounds.

But I keep running into the same wall from the other side.

CHROs know the wall is there.

They need language they can take to their CEO, their board, and their comp committee—language that makes the case before the next key hire walks away. Before they're the one standing in a conference room explaining how much it just cost, and why they didn't bump the range.

The companies that lose top talent aren’t just losing on dollars.

They’re losing on architecture. And no amount of recruiter outreach or employer branding fixes a structural problem—it's the most expensive problem most CHROs never get to name out loud.

So here’s the intelligence I’d normally only share with the person sitting across from you—turned around and pointed at your own process.

Take this as a starting point.

The work begins when both sides stop negotiating against each other and start building toward the same outcome.

Six mistakes. Over and over. And the framework I’ve built—from thousands of negotiations—for how to fix them.

Mistake 1: You’re Paying for the Seat, Not the Outcome

Last fall I advised a senior leader through two competing offers.

The first was an SVP role at one of the largest companies in the world.

Base. Target bonus. Annual equity. New hire grants. A $1 million signing bonus on top.

Total package across the accelerated vesting period we negotiated landed at roughly $4.5 million.

Competitive by every benchmark. Pave-approved. Board-sanctioned.

They turned it down.

They took a VP role at a high-growth public company instead. Smaller title.

Smaller logo on the resume.

We lifted the package to roughly $5.2 million guaranteed across the vesting period—plus $1.5 million in performance accelerators tied to three dated milestones the board was already tracking weekly.

Read that again.

They walked away from an SVP title at a household name. For a VP role at a smaller company that paid more, vested cleaner, and tied every dollar of upside to outcomes the board already cared about.

This is the trade many CHROs don’t think A-players will make.

They assume title and brand carry more weight than they do. They assume the safer, bigger-logo offer wins by default.

It doesn’t. Not with the leaders you actually want. Not with the leaders who actually mean it when they say title isn't everything.

Both companies lowballed from their ceiling.

But the second company wasn’t paying for the role. They were paying for what this leader would do in it. Their upside was much larger—but only in the scenario where the company’s upside was much larger too.

The first company priced the seat. The second company priced the outcome.

This is the fundamental error in how most companies design executive compensation.

HR pulls market data. They build a band. The comp committee approves a range. The recruiter delivers the number. And the number has nothing to do with what the executive will deliver.

Here’s what that structure actually does.

It sets a ceiling on what the executive can earn, no matter how much value they create. And a ceiling isn’t just a cap on compensation—it’s a cap on motivation.

Why would an A-player deliver 2x what you projected? Why would they deliver 5x?

There’s no mechanism that pays them for it.

Their best-case outcome is the same as their base-case outcome. The market rate is the floor, the ceiling, and the whole room.

So they deliver what the structure asks for. Exactly what the structure asks for. And then they start looking for the next seat—the one that lets them bet on themselves.

For your average hire, this works fine.

For the hire who will reshape your trajectory—the one you spent six months recruiting and three rounds of board interviews evaluating—the benchmark is a ceiling on your own upside.

Design compensation around what the executive will deliver, not what the role “should” pay.

Define milestones. Define triggers. Define acceleration tied to the business outcomes that justify the hire in the first place.

When you structure the outcome instead of the seat, you only pay more if they help you win more. Breaking the so-called comp band is funded entirely by the value your leaders create.

Your CFO should love this. Your board should love this.

And the executive you’re trying to land will see a company that thinks the way they think.

Mistake 2: Your Stakeholders Aren’t Aligned on What Success Looks Like

I’ve seen executives whose performance bonuses are tied to metrics their own CEO doesn’t track.

Think about that.

The comp committee approved triggers. The executive signed the contract. And the metrics that determine whether they earn the performance component have no relationship to the outcomes the board is actually measuring the business against.

This happens because comp design is often a conversation between HR and the candidate—with the board hearing about it after the fact.

Sometimes the hiring manager wants to stay out of it. Let HR and the recruiter handle it. Sign whatever lands on the desk.

That’s how you end up with a leader who isn’t aligned to the role before they walk in the door—no matter what the offer letter says.

Because here’s what you don’t see from your side of the table: the executive can’t get to you. The recruiter is gatekeeping. HR is gatekeeping.

Every clarifying question about what success actually looks like has to route through someone who doesn’t know the answer—and the executive knows that going around them costs political capital they haven’t even started to spend yet.

So they stop asking.

They sign a deal with at-discretion bonuses, vague performance language, and triggers that sound like they mean something. And they show up on day one already guessing at what you actually want.

You created an alignment vacuum the moment you decided to be hands-off.

The hiring manager’s goals aren’t reflected in the triggers. The investors’ return thesis isn’t wired into the milestones. The CEO’s priorities live in a board deck that nobody cross-referenced with the offer letter.

The result: a structure where the executive can hit every trigger and the board still considers the hire a disappointment. Or worse—the executive delivers exactly what the company needs and doesn’t earn the performance component because nobody aligned the metrics.

Most corporate comp designers miss something important. The models that work—the ones that align every stakeholder around the same outcomes and reward overperformance instead of just presence—already exist.

They just don’t exist inside corporate America.

They exist in Hollywood. In professional sports. In music. In every industry where the talent is the product and everyone has figured out that the only way to get the best version of the talent is to tie the money to the work.

• A-list actors don’t get base-plus-bonus. They get backend.

• Athletes don’t get cliff vesting. They get escalators for hitting specific, measurable outcomes.

• Producers and showrunners don’t get at-discretion bonuses. They get profit participation tied to “getting credit” for the thing they’re being asked to create.

I’ve spent the last three years advising agents at CAA on deal architecture for actors, directors, writers, and the people they represent.

What strikes me every time I’m in those conversations is how much more sophisticated talent deal structures are than corporate executive comp.

The people building deals for A-list talent have been thinking about alignment, milestone triggers, and compounding upside since the studio contract era ended.

Corporate executive comp is still catching up.

The cleanest example I’ve ever seen of how this should work is public record.

When Tom Brady signed with Tampa Bay, every trigger in his contract aligned every stakeholder.

Win games. Make the playoffs. Win the conference. Win the Super Bowl. Win MVP.

Each trigger was visible, measurable, and created compounding value for every party at the table. Nobody had to interpret “exceeds expectations.”

There was no review meeting where someone had to argue whether he’d earned it. The scoreboard was the review meeting.

The structure eliminated the argument.

Executive comp should work the same way.

The executive, the board, the investors, and the operating team should all win when the same things happen.

If your CMO’s bonus is tied to pipeline acceleration but your board is measuring brand equity and market position, you’ve built a structure that rewards behavior the company doesn’t actually value.

Worse, you’ve forced your CMO to starve the work that makes the pipeline possible in the first place. Brand building. Narrative. Category positioning. The communications infrastructure that turns a cold prospect into a warm one before sales ever picks up the phone.

The CMO cuts the brand budget to hit the pipeline number. Sales closes the warm leads that brand created. Sales takes the credit. The CMO gets measured on the next quarter’s pipeline number—with a weaker brand than the one they started with.

You didn’t hire a marketing leader. You hired a demand gen manager with a bigger title and a budget you’re slowly strangling.

The executive will optimize for what you incentivized—and you’ll be frustrated they optimized for the wrong thing.

That’s not a talent problem. That’s an architecture problem.

Mistake 3: Nobody Can Explain the Deal in Plain English

If your General Counsel can explain the performance triggers but your CHRO can’t—you have a problem.

If the executive you just hired can’t articulate what they need to deliver to earn the performance component—you have a bigger problem.

I’ve seen deals where the executive left money on the table because the trigger was buried in legal language they didn’t fully understand.

I’ve seen comp plans where nobody at the company understood what they’d actually signed—like junior account executives pulling $700,000 a year at $4M ARR companies, because the plan had no ceiling and nobody read it carefully enough to notice.

The AE wasn’t the problem. The plan was—and walking it back later was a much bigger problem.

I’ve seen “exceeds expectations” used as a performance trigger with no dollar value attached—a phrase so subjective it guarantees a fight at review time—or worse, a quiet acceptance the executive will resent until they find a new company to bolt to.

Opacity in comp design doesn’t protect the company. It erodes trust.

When an executive signs an offer they don’t fully understand, they don’t feel grateful.

They feel cautious.

They’re spending their first ninety days figuring out what they signed instead of figuring out how to deliver. Many have buyer’s remorse—and sometimes after relocating across the country.

And the first time a trigger doesn’t pay out the way they expected, you don’t have a comp dispute.

You have a trust collapse and a flight risk.

Transparent governance signals institutional confidence.

It tells the executive: we know what we’re buying, we know what success looks like, and we’re not afraid to put it in plain language.

Make every trigger visible and comprehensible to everyone in the room—the executive, the comp committee, the board. If you can’t explain the deal to a smart person in two minutes, the deal is too complicated.

Mistake 4: You’re Negotiating to Win Instead of Designing to Attract

Procurement mindset applied to talent acquisition.

That’s what most executive comp negotiations are. Minimize cost. Hold the line. Let the candidate know there isn’t much room.

Grind out an extra $250,000 at the offer stage—money the executive earned in the room and you knew you could pay—and lose a five-million-dollar executive eighteen months later because the deal felt extractive on day one.

That $250K, by the way, is roughly what you’ll pay the search firm to replace them.

I have seen this pattern so many times I can predict it from the first email.

The companies that grind every dollar at the offer stage are the same companies whose executives have updated their LinkedIn within a year. Not because the comp wasn’t enough—but because the conversation itself signaled something the executive could not unsee.

It signaled that the company saw them as a cost to be controlled, not a partner to be aligned with.

Here's what CHROs must remember.

This is a shared risk, not a one-sided one.

Your hiring manager stuck their neck out to sponsor the search. Your recruiter put their reputation behind the slate. Your board approved the package. But the executive is also uprooting their life to take it.

They’re leaving a stable seat. Uprooting a spouse’s career. Pulling kids out of schools. Walking away from unvested equity worth more than the signing bonus you’re offering. And in many cases, doing all of that because you poached them.

And then you tell them you can’t do severance. You can’t do a guarantee on year one. You can’t do the relocation grossed up.

You can’t, you can’t, you can’t.

That isn’t fiscal discipline. It’s a failure of basic human decency dressed up as governance.

The negotiation dynamic is a preview of the working relationship.

Executives know this intuitively.

When the comp conversation feels like a fight, they start calculating how every future conversation will go.

Promotion discussions. Resource allocation. Board interactions.

If you’re squeezing me now—when you want me most—what happens when the leverage shifts?

The companies that win top talent don’t negotiate to win.

They design to attract.

They treat the offer as a deal they’re co-designing with the executive, not a number they’re defending from them. And they understand that the negotiation itself is the first piece of evidence the executive has that the company will actually be what it said it was in the recruiting pitch.

Get that part right and the executive walks in already committed. Get it wrong and you’ve spent six months recruiting someone who’s quietly counting the days until they can leave without it looking strategic.

This isn’t soft. It’s strategic.

The $250K you grind for in an adversarial negotiation isn’t a savings—it’s a signal. And it costs you multiples in replacement search fees, delayed execution, and the reputation you’ve now built with every other candidate in the market who talks to the one you just alienated.

Mistake 5: Your Offer Is Invisible to the Market

Many companies treat the offer as an administrative step. HR sends a number. The candidate accepts or counters. Legal cleans it up.

Done.

But the offer is not an administrative step. It is a signal.

A flat, benchmark-matching offer tells the executive you’re replaceable. We’d pay this to anyone in this seat.

A performance-loaded offer tells them we believe you’ll deliver, and we’re willing to invest in that belief.

The difference isn’t dollars. It’s identity.

Last year I restructured the comp architecture for a Fortune 500 leadership team—multiple senior leaders, all in critical seats, all being aggressively poached after the CEO made bullish public statements on a quarterly earnings call.

The competition came hunting within days.

The old structure was failing everyone. Standard base. Standard bonus. Standard four-year vest. The kind of package that reads as “we’d pay this to anyone in this chair.”

Which is exactly what every competing recruiter was telling these leaders on the calls they were taking after hours.

We rebuilt the comp around milestones tied to outcomes the board was already measuring the business against. Combined lift north of $10 million annually across the team.

Life-changing money for the executives.

And for the company, it saved somewhere between $300 million and $500 million in value that would have walked out the door if even one of those leaders had left during the critical execution window—and pulled their teams out with them.

Read those numbers again.

A $10 million annual lift in executive comp protected $300–500 million in enterprise value. That’s a 30-to-50x return on the comp redesign in a single year. (I wrote about this restructuring in more depth in The Deal That Proves Where Executive Comp Is Heading.)

Your CFO will not find a better use of $10 million this year.

Nowhere on the P&L is there a line item where you can spend that and protect that.

This is what compensation architecture actually does when you treat the offer as a signal instead of a cost line.

The best executives self-select toward companies that let them bet on themselves. They want to be somewhere that says—if you’re the real thing, we have a structure that rewards you for proving it.

Your offer design is a talent filter. Not a cost line.

The companies that attract through compensation architecture don’t just get better candidates. They get candidates who show up on day one already committed to outcomes—because their economics are tied to them.

You get the talent you incentivize.

If your structure rewards presence over performance, you’ll attract people who are very good at being present.

And the market is already moving here, with or without you.

The Hollywood-style talent deals migrating into AI research—$100M to $250M packages structured as layered architectures of guarantees, milestone payments, and performance triggers—are not an aberration.

They’re a preview.

The companies competing for the leaders who move markets are already designing this way.

Compensation architecture is becoming a recruiting moat. The companies that figure this out first will not have to outbid their competitors for talent.

They will out-design them.

Mistake 6: Your Retention Strategy Is a Trap, Not a Reward

Cliff vesting. Deferred comp. Repayment clawbacks. Non-competes that read like prison sentences.

This is what most companies call a retention strategy. The executive stays because it’s expensive to go—not because it’s rewarding to stay.

An executive trapped by golden handcuffs is not retained. They are captive. And captive executives do not produce the value that justified hiring them in the first place.

They show up. They protect themselves. They count vesting dates.

And the moment they have a viable alternative, they leave—loudly—and tell every peer and every future employer exactly what your structure felt like from the inside.

I’ve had clients leave $2M on the table to escape a structure that felt like a cage. Two million dollars—forfeited—because the psychological cost of staying exceeded the financial cost of leaving. The equity was designed to vest on a calendar, not on performance.

The only thing keeping them was the clock.

When your retention architecture is built on penalty rather than reward, you don’t retain your best people. You retain the ones who can’t afford to leave.

They often check out and perform worse as a result. The damage a checked-out leader wreaks on a company is difficult and expensive to reconcile.

Your best-case scenario is that they walk away from the handcuffs early—and take the damage with them.

Compounding upside changes that equation.

Milestone triggers that make leaving economically irrational—not because you’ve locked them in, but because the deal keeps getting better every year.

• Year one, the trigger is tied to the strategic initiative you brought them in to execute.

• Year two, it’s tied to the revenue that initiative generated.

• Year three, it’s tied to the margin expansion that revenue produced.

Each milestone builds on the last. Each payout is larger than the one before. The executive who delivered all three is now the most expensive person to replace on your team—and the least likely to leave.

When the next milestone is always more valuable than the last, you’ve created a self-reinforcing loop.

The executive stays because staying is winning. Not because leaving is losing.

That is the difference between a captive workforce and a committed one.

The Architecture

Six mistakes. Six structural failures. And in each one, a principle that fixes it.

Those principles aren’t random. They’re an architecture I’ve built from the other side of the table across thousands of negotiations.

I call it SIGNAL™

S — Structure the Outcome, Not the Seat. Design compensation around what the executive will deliver, not what the role title pays at benchmark.

I — Incentivize Alignment Across Stakeholders. The executive, the board, the investors, and the team should all win when the same things happen.

G — Govern with Transparency. Make performance triggers visible, comprehensible, and articulable to every party from the candidate to the boardroom.

N — Navigate Stakeholder Dynamics Collaboratively. Treat comp design as mutual architecture, not adversarial negotiation.

A — Attract Talent Through Compensation Architecture. Your offer is a signal to the market. Performance-aligned structures attract executives who want to bet on themselves.

L — Lock In Value for All Parties. Create positive retention through compounding upside. When the next milestone is always more valuable than the last, the executive’s best decision is always to stay and deliver.

This is not a theory.

This is what I see working—right now, in real deals, across the market. The companies that adopt this architecture don’t just hire better. They retain longer, align faster, and build teams that compound performance instead of managing turnover.

This shift needs champions.

Not the firms clinging to retained search as a commodity—the ones still running the operating model from 2005. The firms that will define the next era of executive placement are the challenger brands.

The ones with leadership that left the big three because they saw the old model breaking.

The ones willing to tell their clients the uncomfortable truth about why they keep losing the executives they just placed.

The ones building a company-side practice around performance and alignment instead of benchmarks and bands.

If you're one of those firms—you already know who you are.

The market will reward you for moving first.

Both Sides of the Table

I’ve spent my career on one side of this table.

Over 40,000 executive consultations. More than a million text exchanges since 2020. A career built on the belief that no negotiation is predetermined—and that seeing the system is the first step to rewriting it.

The real leverage isn’t in the negotiation.

It’s in the architecture.

When a company builds a performance-based structure—before the candidate even walks in—the negotiation changes.

It gets faster. More collaborative. More honest.

The adversarial dynamic dissolves because both sides are already building toward the same outcome.

The executive doesn’t need to fight for alignment. It’s already in the structure.

The company doesn’t need to worry about overpaying. Every premium dollar is funded by value creation.

And the board doesn’t need to debate whether the package was justified. The milestones answered that question before it was asked.

I wrote this one for the companies with the courage to break out and challenge the market—or be prepared to negotiate with an executive leader who is.

Because when both sides build toward the same architecture, everyone wins.

The talent gets better. The alignment gets tighter. The outcomes get bigger. And the negotiation—the part everyone dreads—becomes collaboration, not confrontation.

The truth is, there aren’t really two sides to this table.

There’s the executive. The CHRO. The hiring manager. The recruiter. The board. The comp committee. The investors. Every one of them carrying their own risk, their own incentives, their own reputation on the line.

The metaphor of “two sides” is useful shorthand, but it’s also what keeps the room adversarial. It frames every conversation as a wrestling match with unfair advantages and shifting leverage—as if somebody has to win and somebody has to lose.

That’s not the work. The work is locking arms.

Everyone in the room building toward the same outcome because the structure lets them. Because the architecture rewards the same behaviors the business rewards. Because the milestones are legible to everyone and the incentives compound for everyone.

Nobody has to give up ground. Nobody has to concede.

The pie gets bigger because the structure makes it bigger—and everyone at the table shares in the growth because the design made sure they would.

If your team is rethinking how it designs executive comp, that’s the conversation I’d most like to have. Book a strategy session.

Stay fearless, friends.

Let me tell you about a deal I almost broke.

A near miss that frustrated everyone.

I was advising a CRO candidate—mid-cap SaaS, $3B valuation, strong growth. The offer was objectively competitive. Top of the band.

Strong equity. Solid bonus target. By every “objective” benchmark, it was a good deal.

She looked at it and said something I’m hearing more and more:

“This comp is built for whoever fills this seat. It’s not built for me or what I’m going to do in it.”

We talked it through.

The deal felt more extractive than creative. It was structured to protect the company’s downside, not to reward her upside.

She knew—because she’d done it twice before—that she could double their annual recurring revenue in 18 months. She had the playbook, the industry-specific relationships, and the track record.

But the offer in front of her priced the role at market rate, not the outcome she’d produce. And it gave her pause.

She wanted a structure that reflected her actual contribution. I agreed. Seems pragmatic.

Long story short—the company lost the candidate.

This is a problem.

The company has spent hundreds of thousands in recruiting costs. Dozens of hours from their most senior leaders. The talent consultancy has spent months building the right slate and guiding the company to their best candidate.

And now—at the finish line—everything stops.

When Cinderella is about to get her slipper, the whole room seizes up.

Buzzkill.

She didn’t know how to advocate for what she needed without sounding like she was asking for a favor—or worse, being combative or difficult.

She had the confidence to deliver a $65M revenue lift but not the language to propose tying her comp to it.

When I offered to create a value-based proposal—she responded with

“What, how? You can do that?”

That gap—between knowing your value and having the words to structure it—is what kills more deals than lowball offers ever will.

Is this a failure in the candidate?

The talent consultancy?

The company?

All three—and it creates a system full of friction that we dismantle one deal at a time.

I’ve watched it happen hundreds of times.

Senior leaders who know they can transform a business but default to “can we bump the base and equity?” Because what else are you supposed to do when everything is locked to band and precedent?

Nobody ever showed them a different frame.

Here’s how deep this goes—when I was researching this article, the AI I use for research and ideation actively discouraged me from challenging standard comp structures.

It kept steering me back toward conventional negotiation tactics. Because the training data is the system—and the system doesn’t have examples of what we’re about to do.

That’s how I know we’re in the right territory.

Creativity doesn’t blossom in the 11th hour when pressure is highest.

And honestly—early in my career—I let a few of those moments pass too, before I understood that the language matters as much as the leverage.

This article is about the language.

If you read the piece two weeks ago, you know what The Performance Signal is—the moment you stop negotiating like an employee and start negotiating like an asset.

If you read last week’s Severance Playbook, you know how to protect the downside before you sign.

This is the how.

The exact scripting, positioning, and tactical framework for proposing milestone-based comp that benefits everyone at the table.

Read the Room Before You Play the Card

Not every company can do this. Not every candidate can pull it off.

And knowing who can is half the battle.

Performance-based comp structures require flexibility—in how the offer is designed, how the board approves it, and how the company thinks about talent as an investment rather than a cost line.

Here’s where this approach has the most traction:

PE-backed portfolio companies. Operating partners think in returns. A comp structure tied to value creation milestones speaks their language. They’re already measuring the executive against a thesis—you’re just asking to participate in the upside when the thesis proves right.

Pre-IPO and high-growth companies. Equity is the currency, milestones are the culture, and the company is actively building the story that makes the stock worth more. Performance-loaded comp is native to how these businesses already operate.

Founder-led companies making their first senior hires. Founders understand betting on yourself. When you say “tie my upside to outcomes,” a founder hears a kindred spirit.

A comp committee at a Fortune 100 hears a headache. (Though we’ve won these over too, they are a pain in the ass and can drag for months. We've got deeper frameworks for navigating the layers here—but that's a longer conversation.)

Companies where the hiring manager or CEO is driving the offer—not just HR. When you’re negotiating with someone who has P&L accountability for the outcomes you’ll deliver, they can see the math. When you’re negotiating with someone whose job is to stay inside the band, the math doesn’t matter.

The following signals tell you the company has flexibility.

• The recruiter mentions equity as a conversation rather than a fixed number. The best will do this.

• The hiring manager talks about what success looks like in the first year.

• The CEO asks what it would take to get you excited.

• Board members are involved in the process.

The following signals tell you to tread carefully and build the case over time. Information gathering through curiosity, patience, and timing control become your #1 priority.

• Rigid comp bands referenced early and often.

• A corporate recruiter who quotes Radford like scripture.

• Proxy statement constraints mentioned in the first call.

• A process that feels administrative rather than consultative.

• “We’re just a startup, you see…”

This isn’t a reason to walk away from those companies.

It’s a reason to negotiate differently—win the base and equity conversations first, then propose what it takes to create a no-brainer after you’ve established your value and the company feels the pull of losing you.

You’re not asking them to break the system.

You’re proposing a pie-expanding opportunity that all parties contribute toward.

But know this—if the execution isn’t precise, this can be reputationally damaging.

You need momentum.

You need to carry learnings from early in the process to substantiate your value proposition.

This isn’t a Hail Mary.

It’s a closing argument built on evidence you gathered from the first conversation forward.

So when the room is right—when do you actually play your hand?

When to Play It

Timing is everything. And the timing is not when most people think.

You don’t introduce milestone-based comp in round one.

• Not when you’re expressing your value to the organization.

• Not when you’re selling the vacation.

• And definitely not as a counteroffer to an unexpected lowball.

You introduce it after three things are true:

The company has committed to you. Not “you’re a strong candidate.” Committed. They’ve told you you’re the one. They’ve asked about your timeline. They’ve introduced you to the board or the team. The emotional investment has been made—and reversing course would cost them more than accommodating your proposal.

You’ve received an initial offer that anchors the base. The base number is on the table. You know their range. You know what they’ve committed to in guaranteed dollars. This matters because the milestone proposal comes as an additive layer—not a replacement for the base, but a structure that sits on top of it.

You’ve already asked the question. Earlier in the process—during the interview dynamic, when information flows freely—you asked: “What are the three outcomes that would make the board consider this hire a home run twelve months from now?”

You documented those answers. Because when the comp conversation arrives, those answers become your milestone architecture.

The sequencing sounds like this:

“I appreciate this offer—it’s competitive, and I respect the structure you’re working within. I look forward to joining you. What’s the chance we can adjust the base and equity? And I’d also love to pair that with a performance structure that makes the overall deal stronger for both of us. I’m no stranger to tying my upside to outcomes—and I suspect that’s one of the reasons we’re all so aligned. Let’s build something neither of us came in expecting.”

You’re not choosing between countering and accepting.

You’re doing something more sophisticated—making reasonable asks on the guaranteed side while simultaneously opening a second lane that makes the total package bigger than a typical negotiation conversation ever could.

The base conversation is familiar territory.

The company expects it.

The milestone proposal is where you change the shape of the deal entirely.

You’re not countering. You’re building. The base adjusts. The milestones are additive. And the first words out of your mouth are acceptance and appreciation—not dissatisfaction.

We’ve made clients millions more per year—and helped companies accelerate their most important initiatives, simply by inviting more creativity and alignment into the negotiation.

And yes—we have a repeatable framework to align all parties.

More on that next week.

Milestones Are Designed Together

A milestone proposal built around your own ambitions looks like a bonus request.

A milestone proposal built around the company’s priorities—informed by everything you learned through the interview process—looks like alignment.

A milestone architecture designed together becomes partnership.

That’s the progression.

And most senior leaders never get past step one. Or really try in the first place.

If you walk in with milestones you invented in a vacuum—revenue targets you’re confident you’ll hit, product launches you were already planning—the comp committee doesn’t see confidence.

They see a rigged game.

You’re asking for a premium on outcomes that were already priced into the role.

But if you walk in with nothing—waiting for the company to hand you the targets—you’ve surrendered the frame. You’re asking them to do your thinking for you.

The move is to propose milestones rooted in what you heard during the process.

• The outcomes the CEO kept circling back to.

• The board priorities that surfaced in your conversations.

• The gaps the hiring manager described when they explained why they needed someone at your level.

You listened.

Now you demonstrate that listening by building a comp structure around what they told you matters most.

“Based on our conversations, it sounds like getting this platform to $150M ARR by Q4 next year is the outcome that matters most to the board. I’d like to propose that if we hit that target together, an additional equity tranche vests. And I’d love your input on refining those milestones so they reflect exactly what success looks like from your side.”

You didn’t invent the goal.

You didn’t wait for them to hand it to you.

You proposed something informed—and then invited them to build it with you.

That’s partnership.

And it’s the moment when people realize that negotiation is not adversarial and scary—but energetic and collaborative.

Does this make the process slower?

Yes.

But it makes the outcome dramatically better—for everyone.

The alignment work that happens in milestone design is due diligence that most hiring processes skip entirely.

You’re pressure-testing expectations, defining success in concrete terms, and surfacing misalignment before day one instead of discovering it at the first performance review.

The companies that complain about a longer hiring process are often the same ones running a replacement search eighteen months later.

This isn’t simply a performance strategy—it’s a retention strategy for both parties.

Double the comp, fired in ten months, eighteen-month search—repeat.

The math doesn’t math—and both sides lose.

You’d have been better off taking half the money at a company that was actually set up for you to succeed.

Getting the job is one thing, keeping the job is another—and conversely—finding high-performing senior leaders is one thing, properly aligning, incentivizing, and retaining them is another animal.

Script A vs. Script B

Let’s make this more tangible.

Script A — What Most Executives Say:

“The offer is solid, but honestly, it’s below what I think I can contribute. I’ve done this before—I took my last company from $60M to $200M in two years. I think my track record justifies a higher number, and I’d like to see the base come up to at least [X] with a stronger equity package.”

This isn’t wrong. It’s what the system taught you to do. And I applaud your courage to push.

But listen to what the comp committee hears.

A candidate who values themselves based on past performance at a different company, asking for more guaranteed dollars with no structural link to future outcomes.

The request is about you—your track record, your self-assessment, your number.

Worse—you’ve got a finger in the air guessing at a higher anchor.

Why that number?

Where did you get it?

If you deliver 2x the revenue for the entire organization, why bump a number up 20-40%? Just cause? That’s not aligned to value creation, that’s only increasing the company’s risk.

Because every candidate they talk to thinks they’re top talent—somebody has to be wrong.

You all can’t be the prettiest girl at the prom.

Value is ultimately subjective.

You want more because you’re supposed to ask for more. And more is better. Right?

And usually you’ll get more because comp committees expect this and budget that into their initial ask in many cases. You’ll just never find the ceiling—so don’t pat yourself on the back too soon.

But the senior leaders who are satisfied with the traditional back-and-forth aren’t the ones reading this.

Another exec who thinks they’re special. We’ve heard this before.

Script B — The Commitment Play:

“I appreciate this offer—it’s competitive, and I respect the structure you’re working within. I’d love to discuss a modest adjustment on the base and equity—and pair that with something I think makes the overall deal stronger for both of us. I’d like us to define 2–3 milestone triggers tied to the outcomes you’ve told me matter most. If we hit $150M ARR by Q4, an additional equity tranche vests. If we close the European expansion ahead of timeline, a cash bridge activates. Your guaranteed cost stays close to where it is. But if I deliver outcomes above the benchmark, the comp reflects that — funded by the value creation, not the budget.”

Script B does something Script A fundamentally cannot.

It accepts the offer.

It signals commitment—gratitude, enthusiasm, intent to join.

You’re not threatening to walk. You’re not manufacturing hesitancy to create pressure. You’re telling them you’re in.

And that’s precisely what makes the milestone proposal so powerful.

You’re making it at the moment of maximum leverage—and using that leverage for alignment instead of extraction. The company isn’t bracing for a fight. They’re leaning in because you just told them you want to be there.

You can still decline later if the structure doesn’t come together—gracefully, professionally, with the relationship intact.

But in this moment, you’re doing something most candidates never do: you’re using your strongest negotiating position to build something collaborative rather than to squeeze.

That alone shifts the dynamic.

You’re not in conflict.

You’re in collaboration—proposing a structure that demonstrates you think like an owner, not an employee negotiating a raise. You heard their priorities and built an architecture around them.

Script A says: “I’m worth more. Pay me more.”

Script B says: “I’m worth more. Let me prove it. And let’s build a structure where proving it benefits all of us.”

One is a negotiation. The other is a business case.

Who would you rather work with?

When They Push Back

They will push back.

Count on it.

Here’s what you’ll hear—and what to say.

1. “We don’t do that here.”

Most companies will say this first. It’s reflexive, not final.

“I understand that’s not standard—thank you for brainstorming and considering this path with me. I can’t help but feel that the standard structure is designed for a different market. I propose we build something that works to reduce the company’s risk while giving me the opportunity to earn more when we deliver. You pay the premium only in the scenario where we’ve created the value that funds it. In my experience, aligning these milestones across the company incentivizes all teams to perform better—that’s our competitive advantage.”

You must reframe.

You’re not asking them to break precedent. You’re proposing a structure that’s more aligned with the company’s success. It will send ripples through all departments and every high-potential or overachiever will lock in and drive the company forward—because every incremental dollar is performance-contingent.

2. “Our comp bands don’t allow it.”

“I hear you. What if we stay within the band and structure the performance component as a supplemental agreement? This will give us an opportunity to further align and turn a good deal into a great deal that’s better for everyone.”

The key word is supplemental.

You’re not asking them to violate their comp architecture—or asking them to stick their neck out for someone they just met. That political capital is hard earned and most are not willing to lose it to help you break precedent.

Rather, you’re asking to build an addendum that sits alongside the standard.

Most comp committees have more flexibility in supplemental agreements than they do in base comp—because the supplemental doesn’t set precedent for the rest of the organization.

If you’re worried about being the tall poppy—about being perceived as aggressive or asking for too much—the supplemental path lets you be ambitious without being threatening.

3. “We’d have to get board approval.”

This sounds like a wall. It’s actually a door.

“That’s a great sign—it means the board would see that I’m willing to bet on myself in ways that help you and them get what they want too. I welcome that conversation.”

A comp committee that brings your proposal to the board is a comp committee that’s already advocating for you.

They wouldn’t surface it if they didn’t want it approved.

The board conversation itself becomes your signal—it tells the entire governance structure that this executive showed up with a business case, not a demand.

4. “What if you miss the milestones?”

“Then I earned exactly what the original offer proposed—and you got me at market rate. The only scenario where you pay above benchmark is the one where I delivered above-benchmark results. That’s the whole point. Neither of us intends to miss—or we wouldn’t have made it this far in the first place.”

This is the strongest response in your arsenal.

It neutralizes the risk objection completely. Every dollar above the base is funded by outcomes.

The company’s downside is exactly what they were prepared to pay anyway.

If I perform average, pay me average.

If I break the mold, break the mold with me.

Kill the “At Discretion” Bonus

While we’re here.

If your offer includes a performance bonus described as “up to X% of base salary, at the discretion of the board” —you’re holding a coupon that may never be redeemed.

It sounds like a sure thing at signing—but it certainly is not.

You must take this seriously.

When I advise clients on their comp, I include discretionary bonuses in my own fee structure. Real skin in the game. Because the moment your bonus is something we both have a stake in, you start asking the right questions—the due diligence that most candidates gloss over because the bonus feels like a guaranteed add-on.

It’s not.

These are real dollars that real people depend on. And they deserve more than “at discretion.”

Discretionary bonuses give the company maximum flexibility and you maximum uncertainty.

A banner year where you crushed every metric?

“We’re being conservative with bonuses across the organization.”

You’re kidding me—again?!

You’ve lived this. We all have. We’ve grown to expect it.

The fix isn’t a higher discretionary percentage. It’s replacing “at discretion” with defined triggers.

“I appreciate the bonus structure. Can we define 2–3 specific outcomes that qualify for the full payout? That way we’re both clear on what success looks like—and neither of us is guessing.”

You’re not attacking the structure.

You’re upgrading it from an ambiguous promise into a contract.

And most comp committees want this—defined triggers make their job easier when justifying the payout to the board.

Discretionary bonuses persist not because companies prefer ambiguity—but because nobody asked them to be specific.

The senior leaders who ask are the ones who collect.

The Lowball Application

What about when the offer isn’t competitive?

When the number is genuinely below market and you know it?

The milestone architecture becomes even more powerful.

Most executives respond to a lowball one of three ways. They walk. They swallow it and resent it. Or they go fractional— “If you can only pay me X, I’ll give you X worth of effort.”

I’ll sometimes advise this path when the fit is right.

But it’s trickier than it looks.

Go fractional without precision and you’ll be perceived as a contractor—a mercenary for hire. You’ve capped your ceiling.

You’ve given them permission to treat you as an operating expense instead of a capital investment—and guaranteed that every conversation about your contribution will be measured in hours or billable days instead of outcomes.

The commitment play works differently.

Accept the lower number—if palatable—and propose milestone triggers that bridge the gap between their offer and your real value.

“I understand the range you’re working within. I’ll accept the guaranteed comp as structured. But I’d like to propose that we tie an additional tranche to the outcomes we’ve discussed. If I deliver [specific board priority], the milestone tranche brings my total comp to where I believe it should be — funded by the value I created, not additional budget.”

You just turned a discount into an accelerator.

You absorbed uncertainty the company would otherwise need to resolve with higher guaranteed dollars. That risk transfer earns a premium. The milestone tranche shouldn’t just close the gap—it should exceed it by 25–50%.

Because you made their economics better in every scenario. And the only scenario where they pay the premium is the one where you massively overdelivered—which means they’re thrilled to write the check.

This Structure Is a Filter

Let’s be honest.

This isn’t for everyone. It’s meant to be a filter.

The executive who proposes milestone-based comp has to deliver.

The structure exposes you if you can’t.

It’s not simply naive confidence.

There’s no hiding behind a guaranteed package when your incremental comp is tied to outcomes with deadlines and dollar values attached.

The same filter works on the company side.

A business that accepts a milestone proposal has to be sophisticated enough to define meaningful targets, measure them honestly, and honor the triggers when they’re hit.

The executives who propose this signal to the market: I perform.

The companies that embrace this signal to the market: We reward performance.

When those two signals meet, you get something neither side can achieve alone—a comp architecture that attracts, retains, and motivates at a level that benchmark-driven competitors cannot match.

That’s not a negotiation.

That’s a competitive moat—for both sides.

Your Move

If you’ve followed this series the last three weeks, you now have the architecture—why the market is shifting, how to protect the downside, and now the language to propose the upside.

If you’re heading into a negotiation in the next 90 days: ask the question early.

• Document what the board considers a home run.

• When the offer arrives, counter with a structure, not a number.

• Frame it as alignment.

• And negotiate the severance before you sign.

Your career is the largest financial asset you’ll ever manage. Build the deal accordingly.

And when you’re sitting across from the comp committee, remember—you’re not asking them to bet on you.

You’re showing them what it looks like when someone bets on themselves.

Everything I’ve written in this series has been for you—the senior executive.

But here’s what I’m increasingly hearing from the other side of the table:

The compensation conversation is shifting.

The smartest companies are figuring this out.

They’re redesigning compensation architecture not simply because they’re losing top talent—but because they’ve realized that performance-based structures attract better talent, retain them longer, and align every stakeholder around the same outcomes.

Next week, I’m writing a piece for the companies. Because the executives who read this aren’t the only ones who need to hear it.

When both sides build toward the same structure, everyone wins.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Nick Richtsmeier runs a podcast called Damns Given, and he asked the kind of questions that make you forget there’s a microphone.

No pre-approved talking points. No safe lanes.

We went places I didn’t expect the Discover Podium origin story, walking away from a $4–5M acquisition, the addiction behind the hustle, why I permanently deleted LinkedIn, and what fatherhood broke open in me that the algorithm never could.

Nick did that.

🎥 Watch on YouTube 🎧 Listen on Apple Podcasts 🎧 Listen on Spotify

Something We Didn’t Get To

Many of you already read Why I Finally Called It Quits With LinkedIn — the most-read, most-shared piece in this newsletter’s history. The podcast with Nick is the unfiltered backstory behind that article—every detail I couldn’t compress into the written version.

But in both the article and the conversation, I circled something I never said directly.

The platform that rewards you with attention is not the platform generating your revenue. And most of us confuse applause for pipeline until the math forces the question.

I built a company on LinkedIn. Scaled it past a million in year one.

Spent five years refreshing ProFinder leads at 3 AM so my team could eat.

And when I finally audited where my actual revenue came from, the deals that changed my life, the clients who stayed, the engagements worth six and seven figures—almost none of it traced back to the LinkedIn feed.

The executive who hires me at that level doesn’t scroll.

They’re not in my DMs. They heard my name from a board member over dinner—or a peer who dropped it in a private Slack thread I’ll never see.

Usually it’s just a text message, “Call Jacob, trust me.”

Meanwhile, the algorithm kept feeding me attention from a room that felt like my market but wasn’t. Every hour I spent performing for that room was an hour I wasn’t in the room that mattered.

This isn’t just a LinkedIn problem. It’s a clarity problem.

If you’re spending four hours a day somewhere—ask yourself where your last three best clients came from.

If the answer isn’t that platform, you’re not building. You’re performing.

The exit isn’t always deletion. Sometimes it’s just proportion. But you have to see it first.

I wrote about this from the inside out—the revenue data, the addiction, the family cost—in Why I Finally Called It Quits With LinkedIn. If you haven’t read it yet, start there. It’s an important piece in the archive.

New Here? Start With These

60+ articles deep. If you want the concentrated version of what this newsletter is about, these five will get you there:

Why I Finally Called It Quits With LinkedIn — The piece behind the podcast. Why I permanently deleted my profile—and what the revenue data actually revealed.

How to Network Without Becoming a LinkedIn Influencer — How to build a high-leverage network without posting “thought leadership,” sending spam, or eating bad cheese at networking events.

Why Executives Leave Millions on the Table: The Werewolf Game Theory of Negotiation — Why most leaders negotiate like villagers instead of winners—and what information asymmetry has to do with it.

Executive Loneliness: Why Climbing Higher Means Feeling Lonelier — What happens when the ladder narrows your world—and how the most effective leaders are reclaiming their humanity.

How Senior Leaders Build Strategic Networks That Create Executive Opportunities — You don’t have a marketing problem. You have a sales problem. This is how real leverage actually moves.

Free Resources You Should Know About

I built a Complete Job Search Course — free, no paywall, no catch.

Full process from positioning to close. If you’re in transition or think you might be soon, start there—and share it with someone who needs it.

For Paid Subscribers

Three things worth knowing:

Career Calibration Calls — Paid subscribers get 25% off one-on-one sessions. We look at your specific situation, your leverage, your timeline — and we build the plan. These calls get credited towards retainers if we end up working together further.

Jacob GPT — A custom AI trained on my frameworks, scripts, and negotiation playbooks. Not a replacement for working with me directly. But it’s the next best thing at 2 AM when you’re staring at an offer letter and your brain has gone quiet.

Monthly Group Office Hours

A live session where I work through real career and compensation challenges with premium members. I send the link via email the Tuesday before each meeting.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Too many senior leaders only think about severance when they’re already out.

The conversation usually starts like this: “Jacob, I just got let go. What can I do about my severance?”

And the answer, usually, is—not much.

We often get something.

But never as much as we could have—and never without the emotional wreckage that follows the deed being done.

The time to negotiate your safety net is before you need one.

• Before you’ve signed anything.

• Before you’ve emotionally committed.

• Before the company knows you’re a sure thing.

Negotiate the terms of your divorce before getting married—when everyone is supportive and full of love.

Because the moment you sign that DocuSign, you’ve surrendered the single greatest source of leverage you’ll ever have in that relationship—the ability to walk away.

I’ve learned across thousands of negotiations that severance isn’t a perk.

It’s a risk mitigation strategy—because you typically pay the brunt of the reputational and financial hardship post termination.

Far more than your organization does.

Especially if you were recruited away from a role where your livelihood and career were relatively safe.

Severance is a structural component of any serious executive compensation package. And the executives who treat it that way—who expect it rather than ask for it—are the ones who walk away protected when the inevitable happens.

And the inevitable always happens.

Why Nobody Talks About This

You just got the offer. The title is right. The comp looks strong.

Your brain is doing what it does after every win—flooding you with the same chemistry that makes you feel invincible after closing a major deal or nailing a board presentation.

Bringing up severance in that moment feels like handing your fiancé a prenup at the rehearsal dinner.

So you don’t.

And that’s exactly what the system is counting on.

Companies aren’t being malicious.

But they understand something you don’t in that moment—that the emotional high of a new offer is the worst possible time for rational financial planning.

The part of your brain responsible for long-term strategic thinking goes quiet when the part responsible for “they picked me” is running the show.

Especially in an employer market.

This is Institutional Homeostasis doing what it does best.

The organization’s immune system resists building protections for your departure during the same conversation where they’re investing in your arrival. It introduces friction. It forces both sides to acknowledge something uncomfortable—that this might not work out.

But here’s what separates the executives who walk away whole from the ones who call me too late—the willingness to have the uncomfortable conversation while everyone is still in love.

Because we’re all adults here.

And adults who’ve led organizations and made decisions that affect thousands of people can handle an honest conversation about protection.

The Leverage Curve

Severance isn’t one-size-fits-all.

There’s a curve—and the more senior you are, the steeper it tilts in your favor.

• At the Director level, 3 months is standard.

• VPs should target 6 months as a baseline—and push for it without hesitation.

• C-suite executives should be looking at 6 to 12 months.

And in the right circumstances—particularly when you’re being recruited away from a stable, high-paying role—we’ve secured 18 to 24 months.

These numbers are generalities—I’ve seen directors get a year and C-suite get 10-year early pension packages.

Never use these as a reason to avoid getting creative.

I’ve also seen leaders negotiate a clause that reads: 6 months of guaranteed severance with 1 additional month added for every year of continuous employment with the company.

The logic is straightforward.

The more senior the role, the harder the landing if it doesn’t work out.

A CMO who gets let go 10 months in doesn’t just lose hundreds of thousands in income.

• They lose 10 months of career momentum.

• They lose the equity they left vesting at their previous company.

• They lose the reputational capital that comes with stability—and inherit the reputational tax that comes with a short, unexplained tenure.

That’s not a one-month-of-base-salary problem.

And this is where most senior leaders get the math wrong.

They think about severance as a function of their new role. It isn’t.

Severance is a function of what you’re leaving behind.

If you’re sitting in a stable position—equity vesting on schedule, bonus trajectory known, institutional credibility compounding—and a company asks you to walk away from all of that, they’re asking you to absorb risk.

Real, measurable, career-altering risk.

Add a cross country move or pulling you into the office full time and we’ve got a lot of life altering changes to consider.

The signing bonus is supposed to bridge that risk.

But most executives treat it like a gift instead of what it actually is—an insurance premium on the career capital you’re forfeiting to take the bet.

Most senior leaders fail to win a signing bonus in the first place. That’s a problem worth its own piece.

The severance package is the backstop.

It’s the thing that ensures you’re not financially devastated if the bet goes wrong—not because you failed, but because the board shifted strategy. Or the CEO who recruited you left a week later. Or the company got acquired and your role was eliminated before you finished onboarding.

I’ve watched all three happen in the last 12 months. To people who are very good at what they do.

The risk isn’t theoretical. The protection shouldn’t be either.

Here’s exactly what to do to win.

Read more

The senior leaders making the most money right now are the ones who asked to get paid less.

Less guaranteed, that is.

From the massive bull market push from ‘08 to ‘20—the COVID hiccup—to the frenzy of inflated activity from ‘21 to ‘24—executive compensation rode a wave that made everyone feel like a genius.

Packages went up because everything went up.

That wave broke.

The last two years have presented a split I’m watching play out in real time across my client base.

On one side—many leaders are feeling defeated and accepting the downward pressure. Settling for deflated packages. Negotiating the same base-bonus-equity structure they’ve always negotiated, just with smaller numbers.

The echo chambers in leadership communities have grown deafening—the downtrodden reinforcing the narrative that this is just what the market pays now.

On the other side—confident senior leaders who get creative.

Who stop negotiating the number and start negotiating the structure. Who propose tying their comp to milestones—and end up making more than they would have in the bull market.

Assuming, of course, that they are as capable as they purport to be.

In a market anticipating poor performance and reducing pay because of it—the true A+ talent is willing to bet on themselves.

I recently helped restructure a Fortune 500 leadership team’s compensation—multiple senior leaders—where we lifted their combined comp north of $10M annually around this exact model.

The old structure was failing everyone—and made top senior leaders ripe for poaching by the competition.

And the competition came aggressively knocking, right after the CEO made public announcements during quarterly earnings calls.

A cutthroat trend that’s increasing during the nuclear arms race to see who wins these AI dollars.

The new structure saved the company between $300M to $500M in value that would have evaporated if even one of those leaders walked during a critical period—and stripped the team out with them—and it put life-changing money in my clients’ pockets.

But this only works if you understand why the traditional structure is designed against you in the first place.

Traditional Structures Fail Everyone

Most people don’t realize that the standard executive comp package is not designed to reward performance. It’s designed to reduce uncertainty and get the deal done quickly.

Base. Bonus. Equity. Four-year vest.

That structure optimizes for presence. Not impact. Not value creation.

For the senior leader:

Every leader walking into a negotiation believes they’re top talent. Very few are willing to back that up with their comp structure. They’d rather take the guaranteed package—higher base, predictable (ish) bonus, time-based equity—and avoid the risk of being measured.

I get it. That instinct is human. Your nervous system doesn’t want uncertainty attached to your paycheck. It wants safety.

But here’s what that safety costs you.

When you crush it in Year 1—when you drive $50M in new revenue or turn around a failing division—what changes in your comp?

Almost nothing.

Your bonus might tick up. Your equity continues its glacial four-year vest. The value you created is captured by the company instantly while you wait years to see a fraction of it.

You’re bearing the execution risk with almost none of the execution upside.

And when it doesn’t work out—when the organization wasn’t ready for what you were hired to do, when the board shifts strategy six months in, when the culture rejects the change agent they recruited—you’re the one explaining a short tenure on your resume.

The guaranteed package didn’t protect you. It just made the failure more expensive to unwind.

For the company:

Hiring the wrong senior leader is one of the most expensive mistakes an organization can make. And the traditional structure makes that mistake maximally painful.

You’re paying full freight from Day 1—guaranteed base, sign-on bonus, equity grants—before you have any evidence the person can deliver in your specific environment.

If it doesn’t work out in 10 months, you’re not just out their comp.

You’re out the recruiter fees, the onboarding cost, the teams they hired who may not survive the transition, the strategic initiatives that stalled, the institutional knowledge that walked out with the predecessor they replaced.

Average executive tenure is shrinking. The cost of a miss is going up. And in this market—where the margin between winning the AI race and becoming irrelevant is measured in quarters, not years—a bad senior hire isn’t just expensive. It’s existential.

The traditional package absorbs none of that risk. It front-loads cost and back-loads accountability.

For the talent firms who place them:

When a firm places a senior leader into a role and that leader doesn’t work out—the firm doesn’t just lose a fee. They may lose the relationship.

Many executive search firms guarantee placements for 12 months. A miss means running the search again on their own dime. But the real cost isn’t the redo—it’s the reputational damage.

The board remembers who brought them the wrong person. Future mandates dry up. Referrals disappear.

A milestone-based structure changes that math.

When all sides define what success looks like before the offer letter is signed—when comp is tied to specific outcomes—the quality of the match goes up. The risk of a bad placement goes down.

There’s a reason advisory firms are circling this space right now. The model is shifting—and the firms that help architect these structures will own the next era of executive placement.

Counterpoint—And Why It’s Actually the Point

The objection I hear most from HR leaders and comp committees is that milestone-based structures take longer to negotiate.

More conversations. More alignment. More complexity.

They’re right. It does take longer.

That is exactly the point.

Companies and senior leaders need to have smarter conversations about what they actually need.

Not vague job descriptions and “at discretion” performance bonuses that nobody can define. Real alignment on what value looks like, what the milestones are, what triggers the upside.

When someone has a meaningful portion of their compensation tied to specific outcomes, they care more about performing. If they don’t perform, the company pays less. If they over perform, the company pays more—and gets dramatically more in return.

This isn’t a new concept.

It’s how every sales organization on earth works.

Close the deal, earn the commission.

But this isn’t commission. Commission rewards transactions. What I’m talking about is rewarding value creation—strategic outcomes, not activity.

We’re not building coin-operated executives.

We’re building compensation architectures where both sides have skin in the game and the incentives are aligned to real value—not a legacy model that persists because that’s the way it’s always been done.

The system resists change—including paying you differently—because the system is designed to protect itself.

That’s Institutional Homeostasis.

And the executives and companies breaking out of that model are the ones winning right now.

The Proof Is Already Here

If you think milestone-based comp is experimental, you haven’t been paying attention.

The Brady Model

When Tom Brady left the Patriots in 2020 and signed with Tampa Bay, the contract was a two-year deal worth $50 million—fully guaranteed. No-trade clause. No franchise tag.

He could have stopped there. He was 42 with six Super Bowl rings. Nobody would have questioned a straight guaranteed deal.

But Brady volunteered to tie an additional $9 million to performance incentives. Up to $4.5 million per year—triggered by top-five finishes in passer rating, touchdowns, yards, completion percentage. Separate triggers for playoff appearances and the Super Bowl.

A player with maximum leverage chose to make part of his compensation contingent on outcomes.

Why?

Because Brady understood something most don’t. When you tie your comp to performance, you aren’t taking a risk.

You’re sending a signal.

You’re telling the other side: I’m so confident in what I’ll deliver that I’ll let you pay me based on results.

The Buccaneers didn’t hear “discount.”

They heard “all in.”

Brady also has the personality to put big hairy goals out there to stay driven—to fuel heavy workouts while his bones beg for him to do anything else.

He won the Super Bowl in Year 1.

Collected the max.

But the incentives weren’t about the money. They were about positioning—telling the organization and the league that he was playing to win, not playing out a contract.

The $250M AI Researcher

Now look at what’s happening in tech.

Meta offered a 24-year-old AI researcher a package worth $250 million over four years—with the potential to earn $100 million in Year 1 alone.

Multiple researchers moving from OpenAI to Meta’s Superintelligence Labs are getting packages in the $100M to $250M range—structured not as salaries but as layered deal architectures with performance conditions, milestone payments, and retention triggers tied to what they actually deliver.

These aren’t comp packages. They’re talent deals.

The stakes are big time right now.

This is how Hollywood has structured talent for decades. How professional sports contracts work. How producers, show runners, and A-list performers get paid—not a flat salary, but a layered architecture of guarantees, bonuses, backend participation, and milestone triggers.

And it’s migrating into the corporate executive suite.

The Rise of Executive Representation

I’m seeing a growing number of executives hand off their negotiations to employment lawyers, advisors, and—in some cases—what can only be described as agents.

Not just for severance. For the entire deal structure.

This is a tectonic shift.

Employment lawyers are the downside folks.

They’re thinking about the divorce—severance protections, termination clauses, non-competes, what happens when things go wrong.

That work matters. Every executive should have it covered.

But most executives stop there.

What I do is the upside.

I’m thinking about the marriage—how to structure the deal so that when things go right, you capture the value you created. Milestone triggers. Performance-based equity acceleration. Comp architectures that reward outcomes, not just presence.

For the talent. For the company. For the talent firm.

I’d argue that you should think this way as well. It’s a much more collaborative and “pie enhancing” mindset.

The downside folks protect you from losing.

The upside folks help you win.

When a senior leader says “let my team handle the details”—they’re not being lazy. They’re being strategic.

They keep their hands clean with the future employer. They maintain the relationship. And their representation fights for protections, milestones, and guarantees that the executive would never ask for directly.

It’s the same reason every professional athlete and A-list entertainer has an agent and a lawyer. The talent focuses on the work. The team architects the deal.

The Fortune 500 is starting to operate the same way.

The Structure Is the Strategy

There’s a name for what happens when you propose tying your comp to outcomes.

I call it The Performance Signal.

It’s the moment you stop negotiating like an employee and start negotiating like an asset.

When you ask for a bigger base, the company hears cost.

When you propose milestone triggers, the company hears confidence.

Same financial outcome. Completely different narrative.

The market is moving here whether you are or not.

• AI talent contracts that mirror Hollywood deal structures.

• Executives bringing in advisors to architect their deals.

• Comp committees experimenting with trigger-based equity because the old model isn’t retaining anyone worth keeping.

The only question is whether you move first—or spend another cycle negotiating base salary increases that don’t compound and equity grants that vest on a calendar, not on value.

I touched on this briefly in my conversation with Lenny Rachitsky.

In the coming weeks, I’ll break down the exact playbook—how to identify the right milestones, how to propose them without sounding like you’re gambling, and how to build a comp architecture that rewards what you actually deliver.

Next week—a special paid-subscriber edition: the exact severance negotiation playbook every executive needs before signing. Upgrade to paid, I’m bumping the tier cost in April.

For now, sit with this question:

If you’re not willing to bet on yourself—why should the company?

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

A lot of you are new here.

Good timing.

This past Sunday, I sat down with for a nearly two-hour conversation about compensation negotiation, career leverage, and why the smartest people in tech consistently leave the most money on the table.

If you haven’t listened yet—or want to revisit it—here’s where to find it:

🎥 Watch on YouTube 🎧 Listen on Apple Podcasts 🎧 Listen on Spotify

To the hundreds of new subscribers—both free and paid—who showed up this week: thank you.

Genuinely.

And to —thank you for the platform, the preparation, and the trust. That conversation doesn’t happen if you don’t create the space for it and take a chance with someone new. <3

Now let me earn your attention.

Something We Didn’t Get To

In the podcast, we talked about why sharing your number too early is dangerous. Why the first figure on the table tends to become the ceiling. Why information and timing create power.

But we didn’t get to name the mechanism underneath all of it.

I’ve been trying to articulate this for a while. The best term I’ve landed on is

The Zombie Number.

Here’s what I mean.

Your last compensation figure—whatever you earned at your previous role—doesn’t die when you leave.

It follows you. (Especially if you let it).

It shuffles from recruiter database to recruiter database, from reference check to “market calibration,” from one offer conversation to the next throughout your network.

It’s dead information—no longer reflective of your value, your trajectory, or the scope of what you’re walking into—but it keeps showing up at the table like it has a seat.

You could be worth $2M.

But if your last package was $800K, the system doesn’t see your potential. It sees your price tag.

And every future offer gets quietly calibrated against a number that was set under completely different circumstances—a different company, a different scope, a different market.

That’s the zombie. The dead following you around. And sometimes we do it to ourselves and believe it about ourselves.

It’s dangerous.

You often don’t know it’s in the room. Nobody tells you that the recruiter already pulled your comp history. Nobody tells you that the “generous” offer they just extended started from your old number and worked up 15%—not from the actual value of the role and worked down to fair.

You think you’re negotiating fresh. You’re negotiating against a ghost.

How to kill it:

Control what comp data exists about you and how people think about you before you ever enter the room.

If you’ve ever posted overly tactical or junior milestones or hot takes on LinkedIn, shared salary details with a recruiter “just to get the conversation started,” or answered “what are you making now?” — you’ve fed the zombie!

I wrote about this dynamic early on in this newsletter—Leaders Share Selectively on LinkedIn—and it’s one of the most important pieces in the archive to understand my mindset about this.

When asked about current comp, redirect: “I’d rather focus on the scope of this role and what a fair package looks like for the outcomes you need. What range are you working with?”

Kill the zombie before it sits down at the table.

Because once it’s there, you’re not negotiating your value. You’re negotiating against a past version of yourself.

And we’re not going back there. Are we?

New Here? Start With These

58 articles deep and counting. If you want the concentrated version of what this newsletter is about, these five will get you there:

Why I Finally Called It Quits With LinkedIn — The piece that went viral. Why I permanently deleted my profile, what the math actually looked like, and what it revealed about the gap between clout and cash.

27 “Offensive” Interview Questions That Flip the Dynamic — Stop auditioning. Start auditing. These are real questions from real clients that changed the power dynamic before the offer ever landed.

The 7 Habits of Highly Toxic Companies — Satirical, pointed, and unfortunately accurate. If you’ve ever worked somewhere that “celebrated transparency” while hiding everything, this one’s for you.

How Senior Leaders Build Secret Hype Networks — You don’t have a marketing problem. You have a sales problem. This is how I actually run my business—and how my best clients run their careers.

The Ultimate Guide to Negotiating Your Comp — The comprehensive GAINS framework walkthrough I wrote for Lenny’s newsletter. If the podcast was the overview, this is the operating manual. Give Lenny some love—he took a bet on this topic before anyone else at his scale did.

Free Resources You Should Know About

I built a Complete Job Search Course — free, no paywall, no catch.

It walks through the full process from positioning to close. If you’re in transition right now or think you might be soon, start there and share it with others.

For Paid Subscribers

Two things worth knowing:

Career Calibration Calls — Paid subscribers get 25% off one-on-one sessions with me. These are strategy sessions—we look at your specific situation, your leverage, your timeline, and we build the plan. If you came here from the podcast and you’re sitting on an offer or a transition right now, this is how we work together. These calls also get credited towards retainers if we end up working together further.

Jacob GPT — Paid subscribers get access to a custom AI trained on my frameworks, scripts, and negotiation playbooks. It’s not a replacement for working with me directly. But it’s the next best thing at 2 AM when you’re staring at an offer letter and your brain has gone quiet.

One More Thing — Monthly Office Hours Are Going Public

I run a live AMA session—office hours, no agenda, bring whatever’s on your mind—on the first Thursday of every month.

Until now, it’s been paid-subscribers only.

This month, I’m opening it up. Thursday, April 2nd. I’ll drop the link in an email next week.

One-time free access—after that, the monthly link goes out to paid subscribers only.

If you want to ask me anything about your negotiation, your transition, your career math—show up. No pitch, no slides. Just the room and the real questions.

No recordings or notetakers allowed.

Thank you for being here.

Whether you found this newsletter yesterday through Lenny or you’ve been reading since Article 1—I don’t take your attention lightly.

The goal hasn’t changed: give you the intelligence, the frameworks, and the language to capture what you’ve already earned.

More soon.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Today is an important personal reflection for yours truly—but first, let me tell you what I’m seeing with top senior leaders in the market—and humbly add deeply intentional perspective.

There has been a shift in tone across my client base the last few months.

A shift I can’t ignore.

The anxiety hits different.

A more palpable tension.

It’s not the usual pre-negotiation nerves or the restlessness of being underpaid. Or the annoyance of corporate bureaucracy—or even the always stressful escalation of performance expectations in a tight market.

It’s deeper and heavier. It’s hitting you square in the jaw.

I’m working with leaders running nine-figure P&Ls who can’t sleep. Executives who’ve navigated three recessions and two IPOs—and are telling me, for the first time, that they feel stuck.

Others have nagging health concerns and family challenges they’ve been avoiding during the rut of the grind post pandemic.

Not just stuck in their careers.

Stuck in their lives.

The white collar tech market isn’t providing optimism. And it’s got a compounding effect.

The weight of an economy that can’t decide if it’s recovering or collapsing.

The geopolitical tension that makes every headline feel like a countdown. AI threatening to reorganize your entire industry before you finish reading about it.

And that’s just the macro.

Zoom in and it gets heavier.

• Aging parents who need more from you.

• Kids navigating a school system that feels like it’s failing them.

• A spouse you barely see because you’re both in the trenches battling to combat endless rising costs of living.

• A body that’s trying to tell you something you don’t have time to hear.

And through all of it, you’re expected to lead with poise, negotiate with precision, and show up like nothing is wrong.

And here I am, telling you to share your cards more strategically to maximize your earnings and leverage—which some misinterpret as hiding your true self, being disingenuous, or manipulative.

I get it. I really do.

Because here’s one thing I’ve learned after 15 years and tens of thousands of conversations with leaders: most of what we focus on could be categorized as “champagne problems.”

They are great problems to have.

• We discuss negotiating between two seven-figure offers, not choosing between rent or groceries or gas.

• We debate whether to take the CEO seat or stay as president, not whether you’ll be employed next month.

• We talk leverage—not navigating a child with special needs or caring for a parent in hospice.

But champagne problems still weigh something.

And when you stack them on top of everything else—the real stuff, the human stuff—that weight can metastasize in something unrecognizable and ugly.

So today I’m not writing about negotiation tactics or comp architecture.

Nothing fantastical or seemingly out of reach.

Today I need to go somewhere more important.

Less

We are not dissimilar you and I. And your boss, competitor, or that investor are not all that dissimilar either.

We all have personal motivations and drivers—and we all face the short end of the stick from time to time. Frank Sinatra simply bellows, That’s Life.

I’ve noticed that the people who best navigate all life throws at them and still seem to have their feet under them appear to have a different point of view.

A sort of effortless poise that’s tricky to place your finger on. A collective confidence that I aspire toward. And it’s not luck or that weird hyper optimistic personality that is more annoying than motivational.

And they don’t have some secret to life.

No, they don’t do more. They don’t have more. They don’t know more.

They do less.

They stop trying to optimize every variable and start asking a harder question—one that most people are often terrified to sit with. Especially in a society that idolizes keeping up with the Joneses.

What would your life look like with less?

Less scrolling. Less performing. Less saying yes to things that don’t compound in the direction you actually want to go. Less carrying weight that was never yours to carry.

Not necessarily less work. Less noise.

Less work saying yes to things that compound in the wrong direction.

I call this The Subtraction Premium.

Can you automate it? Can you delegate it? Can you delete it?

Every framework in the business world is additive.

Add a skill. Add a credential. Add a board seat. Add another zero to the comp package.

I recognize the hypocrisy in me of all people writing that. I’m the guy you call to prioritize and accomplish all those things—and am guilty of going overtly “try-hard” to perhaps overcompensate for past sins.

The entire system is designed to make you believe that the next addition is the one that finally makes you feel like you’ve arrived.

But the leaders I admire most—the ones who actually enjoy the lives they’ve built—got there by removing things. Not adding them.

Maybe you feel this way too.

• They remove the toxic board seat that eats their weekends.

• They remove the “necessary evil” of platforms that tax their nervous system.

• They remove saying yes to every introduction, every favor, every ask that comes dressed as opportunity.

While some express boredom in the early weeks following their scale back efforts—as I check in over time, anxiety doesn’t just decrease—clarity compounds.

You ever hear from folks that say, “I don’t think I could ever fully retire and just fish all the time, it would drive me nuts…?”

I’m not suggesting an extreme elimination diet here—although minimalism is a helluva liberating drug. I’m suggesting measured cuts that you can sit with to bring your world into view—into the present.

Subtraction doesn’t just free up time.

It frees up the cognitive bandwidth your brain needs to make the decisions that matter most.

The ones about your family. Your health. Your next move. Your life.

Too often we spend our careers proving we can add value. But I reckon once you’ve climbed the ladder, the harder skill—the one that separates the executives who are successful from the ones who are successful and at peace—is knowing what to subtract.

Staying

The biggest subtraction I ever made wasn’t a platform or a board seat.

It was subtracting the belief that the world would be better without me in it.

I don’t talk about this often—not because I’m ashamed, but because the gravity of it doesn’t fit neatly into a newsletter about executive compensation.

But today it fits. Today it’s the whole point.

There was a version of me—mid-twenties, broke, homeless, sleeping in a skatepark in Roseville, California—who couldn’t see past the next hour.

A version who drank to disappear.

Who used substances—and fast flings—not to feel good but to feel less. Who convinced himself that the people around him would recover faster from his absence than from his presence.

I often contemplated suicide—hovering the safety on a firearm and standing on the sun bleached green railing of the Foresthill bridge.

But I’m still here.

That’s not a sentence I write for sympathy.

I write it because everything—everything—that I’ve built, every client I’ve served, every framework I’ve developed, every word of this newsletter, my wife, my boys, and our future—exists on the other side of a decision I almost didn’t make.

The decision to stay.

There was no dramatic turning point.

No rock bottom movie scene. Just a slow, stubborn, unglamorous choice to keep going. I will say, a timely flip on the radio to Tim McGraw’s “Let It Go” changed my decision one fateful afternoon—and now every time I hear it you can queue the waterworks.

Then I kept choosing it again the next day. And the one after that.

Then I met Mary.

She came from circumstances as brutal as mine—worse even—and had every statistical reason to accept a predetermined future.

But she refused. She had faith—the kind that rebuilds a life from the studs. She had agency and conviction about what her life would be, and she wasn’t afraid to ask for it.

And she had it at twenty years old. Good grief.

She showed me that the story I’d been telling myself—that my future was already written—was a lie.

I’ll write more about this in my upcoming book. But the short version is: Mary showed me I had the agency to save myself.

That changed everything.

On January 1st, 2022, I made another subtraction as Mary and I got serious about having children. I stopped drinking entirely.

Raising children forces you to relive past trauma—but in experiencing your babies grow—the experience matures and heals your trauma. You didn’t deserve that pain, you were just a kid.

I never want my children to experience how substance abuse and domestic violence will slowly rip a family apart.

As I write this, I’m over 1,500 days sober.

However, I didn’t get sober because I had some profound revelation.

I got sober because I finally understood that alcohol was compounding in the wrong direction. Every drink borrows clarity from tomorrow. The interest rate is brutal.

Sisyphus had better odds.

My faith deepened in this season.

I started to see the evidence of something deliberate in my life. Too many close calls. Too many doors that opened when every logical outcome pointed to a dead end. At some point, coincidence stops being a satisfying explanation.

Sobriety didn’t add anything to my life. It subtracted the thing that was blocking everything good from getting in.

And what rushed into that space—once I stopped filling it with noise and poison—was gratitude.

Not the motivational poster kind. Not the “write three things in your journal” kind. Just the peace of knowing how a few key decisions and my present reality would be an unattainable dream otherwise.

The kind where you’re sitting on a porch in Montana with your beautiful partner and two boys and the spring air hits your face and you think—God, thank you—I almost didn’t get this.

Any of this.

That kind of gratitude simply needs space to exist.

And space only comes from subtraction.

Your Brain Can’t Hold Both

Mary told me something years ago that I didn’t believe at first.

I was spiraling—monologuing about how the weight of everything was getting to me as the CEO of Discover Podium.

How I wasn’t sure what to tell my staff who were drowning in the same anxiety I was feeling. You know, small businesses surviving COVID stuff.

She listened, then said two words.

Be grateful.

I pushed back. No way.

She didn’t flinch. “Your brain cannot process anxiety and gratitude at the same time. So be grateful.”

I fat-fingered a Google search to prove her wrong. Harvard agreed.

She was right. A comment I did not mutter vocally.

Here’s why this matters for you—not as a platitude, but as a biological fact.

When anxiety takes over, your brain shifts into threat mode.

The same system that kept your ancestors alive when a predator was circling now fires when you open your inbox, read a headline about tariffs, or sit across from a CEO who’s about to discuss your future.

Your heart rate spikes and your thinking narrows.

The part of your brain responsible for strategic decision-making—the thing you’ve spent your entire career sharpening—goes quiet at the moment you need it most.

You’ve felt this.

The moment a comp offer slides across the table and your mouth says “that sounds fair” before your brain catches up. The meeting where you had the perfect response rehearsed and forgot it the second the room got tense. The Sunday night dread that eats your evening before Monday even arrives.

That’s your chemistry.

But gratitude—real, deliberate gratitude—interrupts the loop.

It activates a different system entirely. One that lowers cortisol, restores clarity, and gives your prefrontal cortex back the oxygen it needs to function.

• You can’t white-knuckle your way out of anxiety.

• You can’t think your way past a threat response with more thinking.

• You can’t simply be tougher and more disciplined—which is likely how you’ve overcome most other things that get in your way. What got you here, won’t get you there.

However, you can replace it.

Gratitude isn’t the absence of anxiety. It’s the antidote.

This is why subtraction matters beyond your calendar and your commitments.

When you subtract the noise—the doom scrolling, the performative obligations, the relationships that drain you, the LinkedIn humblebragging—you create space for gratitude to do its work.

And when gratitude is running the show instead of anxiety, you make better decisions.

You lead with more clarity. You show up for your family without the static in the back of your head.

You no longer have to do challenging things; you get to do challenging things.

For them.

If you think back on how you’ve gotten to where you are today, you can objectively say that in most cases you make great decisions.

If you’re reading this article today, you are already performing in the top percentile of people globally—at least according to what our society tends to value.

Trust yourself to continue—and that your champagne problems are a reason to celebrate.

Gratitude is not soft.

It’s the hardest reframe most leaders will ever attempt.

Because it requires you to stop focusing on additive performance long enough to feel something real.

When your clarity becomes abundant—your ability to negotiate for your life becomes second nature. You won’t even need to call me.

What Would Your Life Look Like With Less?

I ask my clients this question more than any other.

More than “what’s your target comp?” More than “what’s your walkaway number?”

Because the answer reveals everything.

About a decade ago, I worked with a couple in Los Angeles. Husband—a high-profile HBO executive, early fifties, making $1.2M a year. Wife—a CMO in Orange County, earning around $900K.

No children. Eight figures in the bank.

The husband was diagnosed with stage one cancer. His doctor warned that the stress of working would likely kill him—but he was three years short of full pension.

The wife, meanwhile, was laser-focused on landing a higher-paying CMO role. When I pressed on why, the answer was simple—she wanted to finally out-earn her husband. Perhaps to give him permission to stop. But neither of them needed to work. They didn’t even need to live in Los Angeles.

What do you think their life would look like with less?

When she asked what she should do, I told them to take four weeks of PTO in Hawaii and leave their phones behind.

They chose to retire on the flight home.

They’re both still enjoying themselves today.

Most executives only consider what less looks like near the twilight of their career.

They’ve optimized relentlessly—for title, for comp, for prestige, for the next rung—but too many have never stopped to ask whether the ladder is leaning against the right wall.

And in chasing their maximum potential—they often forget to live in the moment. Or worse—they live for someone else’s moment.

Money decreases in value as we age. It’s taxed. Inflated. Stripped away.

Yet time increases in value as we age. It grows scarce.

We’re quick to lose every negotiation by trading time for money.

So, I ask: what would your life look like with less?

When I ask, the room usually goes quiet. Not because you don’t know the answer. Because you do—and you know you can do something about it.

It’s some combination of less.

Less obligation. Less performing. Less carrying the expectations of people who wouldn’t carry yours.

• Sometimes the answer is cutting a board seat you’ve been dreading for two years or quitting a toxic, unethical, or misaligned company.

• Sometimes it’s leaving a city you hate living in.

• Sometimes it’s ending a relationship you’ve outgrown but maintain out of guilt.

• Sometimes it’s tossing the device in your pocket that steals more than it gives.

• Sometimes it’s deleting all social media accounts and becoming a digital ghost.

• Sometimes it’s removing addictive highly processed food, seed oils, sugar, alcohol, and substances.

The answers are always specific. And they’re always obvious—in hindsight.

This week, consider a strategic audit of your life.

Write down three things you’re carrying that aren’t compounding in the direction you want to go.

Be honest. Nobody sees this list but you.

Then ask yourself—for each one—can I automate it, delegate it, or delete it?

You don’t have to act on it today. Just name it. Because the act of naming it—of pulling it out of the background static and putting it on paper—is itself a subtraction.

You’re taking something that’s been quietly taxing your nervous system and forcing it into the light where it loses half its power.

And then write down three things you’re grateful for.

Not the things you think you should be grateful for. The real ones. The ones that hit you in the chest when you’re not performing for anyone.

Your kid’s laugh at dinner. Waking up healthy. A partner who sees through your armor and loves what’s underneath. The career you’ve built—even when it’s heavy—because you built it. That’s yours.

Hold both lists.

The things to subtract. The things to protect.

That’s your compass. Not your comp band, not your title, not the market—that list is your compass.

There's a rule in aviation—if a plane is off by a single degree at takeoff, it drifts one mile for every sixty flown.

The pilot doesn't feel the error. The passengers don't feel the error.

But after enough distance, the plane lands somewhere it was never meant to be.

This is why the audit matters.

You're not looking for catastrophic misalignment. You're looking for the one-degree drift—the thing that feels small today but is quietly compounding you toward a destination you never chose.

Consider:

• A 12 ounce soda a day is 10lbs of extra calories a year.

• 30 minutes of lost sleep every night is a month of sleep debt a year.

• Sitting an hour longer every day increases cardiovascular risk 14%.

I spent the first half of my life adding—clawing, building, chasing, numbing, performing. I spent the second half learning that the things I subtracted gave me more than anything I ever earned.

Sobriety gave me more than any deal I’ve closed. Faith gave me more than any framework I’ve named. My family gives me more before 7 AM than my career gives me all year.

Trust me.

And gratitude—the simple, stubborn, daily practice of noticing what’s already here—gave me back a life I almost threw away.

You don’t need more.

You might just need less.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

The game is Werewolf—and the rules are simple.

A group of players gather.

Think of a table of 12. Cards are distributed at random.

10 are “Villagers.” 2 are “Werewolves.”

The Werewolves silently reveal themselves to one other. The Villagers remain clueless.

The game unfolds in a cycle of Day and Night.

Each day, the group debates and votes to eliminate a suspect. If the Villagers execute both Werewolves, they win.

However, the Werewolves win the moment they reach numerical parity with the Villagers. If the group thins to the point where Werewolves make up half the table, the Villagers lose their voting power, and the monsters take the town.

The werewolves win over 60% of the time despite 5:1 odds.

Why?

Not because they are stronger, but because they are informed.

In a room full of blind accusations, the only people who know the truth are the ones trying to kill you. The game isn’t about finding monsters—it’s about how easily the people with information destroy the people without it.

Werewolves win because they have information the majority doesn’t.

They know who’s on their team. They know who’s dangerous. They know exactly what’s true while everyone else is guessing.

The villagers?

They’re debating in the dark—building theories off of body language and gut feel, reacting to whoever talks the loudest or acts the most suspicious.

The informed minority doesn’t just have an edge. They control the game.

Now replace “werewolf” with “employer” and “villager” with “you sitting across the table in a negotiation you think is a conversation between equals.”

It’s not equal. It never was.

You’re debating in the dark—building theories off of Glassdoor reviews and “market benchmarks,” reacting to a recruiter’s tone of voice or a vague promise of “growth potential.”

The informed minority doesn’t just have an edge. They own the map.

The Villager’s Real Problem

Herb Cohen—one of the most respected negotiation minds of the last century—argued that every negotiation comes down to three things: Information, Timing, and Power.

Most executives obsess over the wrong ones.

They walk into negotiations leading with credentials and logic.

• Here’s my track record.

• Here’s my P&L impact.

• Here are three reasons I’m worth more.

Or they focus on timing and leverage.

• I’ll wait for the right moment.

• I’ll let competing offers do the talking.

But Cohen understood that power and timing are derivatives.

They’re downstream.

The thing that feeds both of them—the thing that makes the other two actually work—is information.

Without it, your power is a bluff and your timing is a guess.

But you don’t simply gather information by asking hard questions. You get it by making the other person want to tell you things.

This is where you must apply your ability to influence and persuade. These are the soft skills that turn mediocre 6 figure deals into 7 figures and beyond.

The executives I work with who collect the best intelligence aren’t interrogators.

They’re the ones who walk into a room and make the recruiter, the hiring manager, and the CHRO feel like they’re on the same team.

They lead with curiosity, not credentials.

They say things like, “I want to make sure this is a win for your team too—help me understand what success actually looks like in this role from your side.”

They give the other party a version of themselves worth living up to—the collaborative partner, the transparent leader, the person who solves problems rather than creates them.

More alignment, less confrontation.

And in doing so, the other side opens up.

• They share the real timeline.

• They reveal the internal politics.

• They sometimes even tell you what the last person in the seat was paid and why they left.

Not because you cornered them and drilled them with an aggressive ultimatum—but because you made it feel safe and smart for them to be honest with you.

Credentials get you in the room. Logic keeps you in the conversation. But emotion—deployed with precision and empathy—is what gets people to hand you the map.

The Werewolf problem plays out in real time across every executive negotiation I advise.

The company knows the approved band. They know the internal equity concerns. They know how desperate the hiring manager is to fill the role, how many other candidates fell through, and exactly how much budget flexibility exists above what they offered you.

They know whether the role was created for you or if you’re the fourth-choice candidate they’re trying to close before the req expires.

You know what they told the recruiter to tell you.

That’s not a negotiation between equals. That’s a villager raising their hand in the dark.

My role is to be the seer.

In the last year across my client base, the executives who consistently outperformed—who landed 40, 70, and sometimes 200% above initial offers—all had one thing in common.

It wasn’t better credentials. It wasn’t harder negotiation tactics.

They showed up informed—which helped us get more creative.

• We knew the company’s hiring urgency before the first call.

• We knew the internal politics around the role.

• We mapped the decision-makers and understood whose opinion mattered versus whose was theater.

• We did the work before the game started—while everyone else was waiting for an offer letter to figure out where they stood.

We didn’t show up to debate in the dark. We showed up with the map—and the other side never knew we had it.

How to Become the Seer

In Werewolf, there’s a special role called the Seer.

Each night, while the werewolves hunt, the Seer gets to look at one player’s card and learn the truth. The Seer gains more power than anyone else at the table because they have more information—and that changes everything about how they play.

The Seer doesn’t argue louder. They don’t need to.

They ask better questions because they already know things the room doesn’t. They guide the conversation without revealing their hand. They move with precision while everyone else moves with panic.

That’s the role I play for my clients.

But it’s also a role you can build for yourself—if you’re willing to do the work before the game starts.

Here’s what most executives do:

• Get a call from a recruiter.

• Get excited. Jump on the phone. Answer every question openly.

• Share expected comp when asked.

• Wait for an offer and react to the number.

• Try to negotiate from a position they didn’t build.

Here’s what the best-informed executives do:

• Before the first call, they’ve mapped the company’s leadership and identified who owns the hiring decision—not just who’s conducting the interview.

• They understand the market players, pressures, and opportunities.

• They’ve worked their network to understand the internal politics around the role.

• They know whether this is a backfill, a new position, or a rescue hire—because each one carries a completely different urgency and budget.

• They’ve talked to people who’ve left the company and understand the real culture, not the careers page version.

• They understand the comp philosophy—whether this company pays at the 50th, 75th, or 90th percentile—and they know where the flex exists.

• They remain intellectually curious to find new information that will help them create more value for everyone—giving them an opportunity to break the status quo.

Script A — The uninformed executive says: “I’m really excited about this opportunity. Here’s what I’d like to make—I won’t go backwards or laterally at this stage in my career.”

This approach reveals information and collects nothing.

Script B — The informed executive says: “I’ve spent time understanding your business and where this role fits into your growth plan. I’d love to understand from your perspective—what does an ideal outcome look like for this hire in the first twelve months, and what would make the investment feel like a no-brainer for your team?”

This approach collects information and reveals nothing.

Same conversation. Completely different control of information.

Script A hands the company your card.

Script B makes them show you theirs—without ever feeling like they’re being interrogated.

You must lead with alignment. You give them a version of themselves to live up to—the thoughtful company that invests in the right leader, not the one that grinds on nickels.

And when information flows in your direction, the entire negotiation shifts with it.

Because the real unlock isn’t arguing over a bigger base or a better bonus. It’s proposing structures nobody else at the table was thinking about.

When you understand the company’s actual priorities—the revenue target that keeps the CEO up at night, the market share play the board approved last quarter, the product launch that has to land—you can tie your compensation to their outcomes.

Milestone triggers. Performance accelerators. Equity kickers that only vest if you deliver what they already told you they need.

This is how the best deals in Hollywood and professional sports get structured. Why is it so different in corporate?

The base is the floor. The real upside is engineered around performance—and both sides win because the incentives are aligned, not adversarial.

You can’t propose that structure if you showed up uninformed. You can’t expand the pie if you don’t know what’s in it.

But when you’ve done the intelligence work—when you understand what the company is actually trying to build—you stop negotiating for a number and start designing a deal.

I push every client I work with to think this way.

And the most forward-thinking CHROs, talent consultants, and comp committees are starting to arrive at the same conclusion from the other side of the table—because this model solves their biggest problems too.

High performers naturally break compensation bands.

That’s not a bug—it’s a signal.

A performance-aligned structure lets companies reward that outsized impact without blowing up internal equity, because the upside is tied directly to outcomes that justify the spend.

And underperformers?

They earn less—not because someone made a subjective judgment call, but because the structure was honest from the start.

There’s a tell here too.

The executives who embrace performance incentives are signaling something—confidence, conviction, a willingness to bet on themselves.

The ones who push back and demand a larger guarantee? They’re telling you something equally important.

Which one would you rather hire?

This is the next generation of executive compensation.

• Longer executive retention because the deal is more balanced.

• Better performance because the incentives are real.

• Less adversarial negotiation because both sides built the map together.

The market is moving here.

The candidate who shows up informed isn’t a harder negotiation.

They’re a better hire.

The Game Is Already Happening

Too many people think negotiations start when someone slides an offer across the table.

It doesn’t.

• It started the moment the recruiter looked at your LinkedIn profile and decided what you were worth before you said a word.

• It started when the hiring manager described their ideal candidate to HR and HR translated that into a comp band you’ll never see.

• It started when the company decided how much budget flexibility to hide and how much to reveal.

• It started when someone in your network got asked about you—and you had no idea what they said.

The game was already happening. You just weren’t playing yet.

And if you’re on the company side of the table—every time you default to opacity, you’re not protecting the budget.

You’re building a trust deficit that compounds until your best people leave.

Not today. Not in the interview. Eleven months in, when the resignation letter arrives and you’re back at the table paying a premium to replace someone who never should have been lost in the first place.

The informed minority will always outperform the uninformed majority.

That’s true in Werewolf. It’s true in executive compensation. And it’s true whether you’re the candidate or the company.

The only question is which side of the information you’re on.

Stop playing the villager.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

In the last 12 months, I’ve negotiated more relocation bonuses than in the previous decade combined.

That’s not a typo.

For three years, the narrative was clear—remote work won. Senior leaders could live wherever they wanted, fly in for the occasional board meeting, and run billion-dollar P&Ls from their home office in Montana.

The talent had the leverage, and geography was dead.

That narrative is quietly fading—although I know many executives kicking and screaming for it not to be the case.

I’ve heard it from several of the most respected headhunters in my network, and I’m seeing it play out in real time across my client base: the days of remote work for the C-suite are behind us.

Not winding down. Behind us.

And it’s showing up in three ways that matter:

Frequency. Relocation is back on the table for major roles—not as a nice-to-have, but as a prerequisite. Companies that spent 2021-2023 competing for remote-friendly talent are now quietly removing “remote” from their senior leadership searches.

Amounts. Relocation packages are spiking. The numbers I’m seeing today would have been laughed out of the room two years ago. Companies are offsetting inflation, cost-of-living gaps, and the sheer friction of asking someone to move their life—and they’re paying real money to do it. I closed a $250k cross-country relocation for a C-Suite leader at a $1 billion company just a few weeks ago—plus an 18 month severance to mitigate the risk.

Willingness. Talent in transition is ready to move again—perhaps not because they want to, but because that’s what’s available to them. The white-collar squeeze is real. The executives who spent the last few years comfortably remote are watching the best seats go to candidates who are willing to be in the building. And they’re adjusting.

This is a leverage moment hiding in plain sight. The executives who see it early are walking into relocations with six-figure bonuses and ironclad protections.

Everyone else is negotiating for a moving truck.

Don’t be the latter.

The Mortgage Rate Trap

I know what some of you are thinking.

I’ll wait it out. The pendulum will swing back. There’s no way companies can sustain this.

I’ve heard this before. It sounds a lot like something else I’m hearing from clients right now in a completely different context.

Holding out hope for a (premium opportunity) remote C-suite role is like holding onto a home you’ve outgrown because you’re locked in at 2.6%.

On paper, it looks smart.

You’re protecting a rate that doesn’t exist anymore. But meanwhile, your family has outgrown the space, your commute to the life you actually want is getting longer, and every month you stay, the opportunity costs compound in ways you can’t see on a spreadsheet.

I fear that’s what’s happening to remote-first executives right now.

Living in Franklin, Tennessee, or Incline Village, Nevada, or Whitefish, Montana—or any of the upstart remote-dominant towns that boomed between 2020 and 2023—won’t be doing you any favors anymore.

Not in this market.

The companies filling the biggest seats are demanding presence. Not because remote leaders can’t perform—many are exceptional. But because the nature of what leadership requires is shifting underneath everyone’s feet.

AI isn’t reducing the workload at these companies. It’s intensifying it.

Expectations are expanding faster than headcount.

The scope of what a senior leader is expected to own, influence, and decide is growing—and the executives who are physically present, visible to the people who control their trajectory, and embedded in the operating rhythm are the ones getting the most critical assignments, the most political capital, and the strongest positioning for their next move.

The remote executives?

They’re delivering results from 2,000 miles away and wondering why they weren’t in the room when the decision got made.

It’s easier to forget about a Slack notification than a raucous happy hour after a grueling day in the city. Leadership remembers how they feel working with you in person—a ping on the computer is more nuisance than memorable.

This is creating a divide that may define the next decade of executive leadership.

The leaders who lean into proximity and use AI to multiply their visible impact will become spectacularly valuable. The ones who optimize for geographic comfort will quietly become interchangeable.

As someone living closer to ski slopes than skyscrapers—I’m okay with that tradeoff.

This isn’t to say you’re not valuable by choosing lifestyle over maximal career ambition. I’m simply noting that it is a conscious choice we must make and understand together.

If you’re in transition right now and a relocation is on the table, stop treating it as a sacrifice.

It might be the most valuable leverage point you have.

A Premium Price On Displacement

I haven’t seen anyone talking about this yet—and it’s the reason I negotiated that 18-month severance alongside the $250K relocation I mentioned earlier.

Most executives treat a relocation bonus like a moving expense. Help with the truck. A few months of temporary housing. Maybe a cost-of-living adjustment if you’re moving from Austin to Manhattan.

That’s thinking like an employee.

Here’s how I want you to think about it instead.

The moment you relocate for a role, you are transferring institutional risk onto your personal balance sheet.

I call this “Displacement Premium”—and once you see it, you won’t think about it the same again.

Think about what actually happens when you say yes to a cross-country move.

• You sell a home or break a lease.

• You pull your kids out of their schools.

• Your spouse leaves their professional network—maybe their job.

• You walk away from your doctor, your community, the neighbors who watch your house when you travel, the friends who show up when things get hard.

You are liquidating your personal infrastructure to serve the company’s operational needs.

And here’s the part that will cost you the most if you don’t see it coming: if that role doesn’t work out in 18 months—a bad culture fit, a PE restructuring, a new CEO who wants their own team—you’re not just unemployed.

You’re unemployed in a city you moved to for a job that no longer exists, surrounded by a support system you don’t have yet, with a mortgage on a house you bought under pressure to “get settled.”

That risk has a price.

And most executives never collect it; perhaps because they’ve been out of work for an increasingly uncomfortable period and need to end the bleeding.

A major life decision made in urgency is dangerous. Once you’ve relocated, something shifts in how you operate—and it’s not strategic, it’s biological.

The same executive who made fearless decisions for twenty years suddenly starts rationalizing a bad situation.

It’s not that bad. I can make this work. The culture will improve.

Not because the situation improved—but because the cost of leaving just tripled. Your brain starts treating the job as survival because walking away now means uprooting everything again.

You become less likely to push back. Less willing to negotiate mid-role. Less willing to walk when walking is exactly what you should do.

The golden handcuffs cinch a notch tighter.

The company gains silent leverage over you precisely because you moved.

This is why the severance conversation has to happen in addition to the relocation conversation.

Before you move, you have maximum leverage—they want you badly enough to ask you to uproot your life. After you move, you’ve absorbed the risk.

The negotiating window doesn’t just narrow. It closes.

Every relocation should come with a Displacement Premium baked into the offer: a package that reflects the actual risk you’re absorbing, not just the cost of the moving truck.

The Private Equity Problem

Now let’s talk about the elephant in the room—because there’s a version of this conversation that gets a lot harder depending on who’s signing your offer letter.

If you’re negotiating with a founder-led company or a public enterprise, the relocation and severance conversation is usually straightforward.

There’s a human on the other side who understands the ask, has budget flexibility, and can see the logic of protecting a leader they want to retain—if you’ve done your job driving and selling the value and vision of working together successfully.

Private equity is a different animal entirely.

In the last six months, I’ve been involved in several PE-backed transitions where relocation, severance, and/or retention was on the table.

The pattern is consistent enough that I want to name it.

PE firms rely on precedent and downward pressure.

Their playbook is built on standardization—what the last executive accepted, what the comp data says the role is “worth,” what the portfolio company’s existing structure allows.

Everything is benchmarked. Everything is controlled. The conversation starts at the floor and resists moving.

You’re often beholden to how well the senior leadership team negotiated before you—and let me tell you—it’s usually not very good, hence why I do what I do.

But here’s a structural contradiction that we all see—but don’t want to say out loud.

These firms will spend $2 billion acquiring a company and then fight an executive over a $200K package.

They’ll demand geographic presence—insist on it, actually—but refuse to compensate for the risk of that presence.

They’ll acquire a business, restructure the leadership team, require the incoming CEO or CRO to relocate to headquarters, and then offer a standard package that treats the move like a minor inconvenience rather than a major life disruption.

It reveals something about how PE compensation philosophy actually works.

They’re optimizing for control, not partnership.

The leaders running their portfolio companies aren’t treated as people navigating complex life decisions—they’re treated as operating components.

Interchangeable assets to install, optimize, and swap out when the model requires it.

This isn’t typically malicious. It’s structural—it’s devoid of emotion—it’s what we reward in capitalism.

PE firms operate on models, multiples, and precedent.

The human cost of a relocation doesn’t show up in their framework because their framework wasn’t built to account for it. But the result is the same—the executive absorbs outsized risk while the firm retains maximum flexibility to replace them.

We need to rewrite the script so that human capital is perceived as more valuable. Now—perhaps more than anytime in history. We need to realign the expectations of the executive compensation committees and challenge them to make the necessary changes to protect human capital and the costs associated with losing premium talent.

So how do you win this negotiation when precedent and logic and comp data are all being used against you?

You don’t fight data with more data.

You can’t out-benchmark a PE firm. They have more precedent, more comps, and more willingness to walk than you do.

Instead, you win the behavioral psychology battle. And you do it invisibly.

Tactics

The standard playbook says: present your data, make a logical case, anchor high, and negotiate toward the middle.

Against a PE firm, that playbook gets you exactly what they already planned to give you.

I’ve learned this the hard way across dozens of PE-backed negotiations. Logic doesn’t move them. Credibility doesn’t move them. Precedent definitely doesn’t move them—because they own the precedent.

What moves them is rhetoric, emotion, and methodical long-term pressure. Being the squeaky wheel—but doing it in a way they never see as squeaking.

Here’s the difference in practice.

Script A — Employee Mindset:

“I’d like to discuss a relocation bonus. The cost of living difference between Nashville and San Francisco is significant, and I’d appreciate help with the transition.”

This gets you a moving stipend and a pat on the back.

Script B — Displacement Premium Mindset:

“I’m excited about this opportunity and I want to make this work. But I want to be transparent—relocating my family is a significant commitment that adds real personal risk to this transition. I’d like us to structure the relocation package and protections in a way that reflects that commitment, so I can focus entirely on delivering results from day one instead of managing downside scenarios in the back of my mind. I’m sure if you were in my shoes, you’d be thinking about all of this too—what would you ask for? I respect your read on the risk.”

Notice what Script B does. It doesn’t argue about data. It doesn’t cite comps. It doesn’t make demands.

It makes the decision-maker feel the weight of what they’re asking.

That’s the behavioral shift.

You’re not fighting their framework. You’re operating outside of it—in the space where human beings make decisions based on fairness, reciprocity, and the discomfort of asking someone to sacrifice without acknowledging it.

Against PE, this is a long game.

You don’t win it in one conversation. You plant the seed of fairness early, you reinforce it consistently, and you create just enough friction that the path of least resistance becomes giving you what you’re asking for—rather than fighting you on it.

Here’s what to put on the table:

Lump-sum relocation bonus—not reimbursement. Reimbursement caps your upside and requires you to document every expense. A lump sum signals trust and gives you flexibility. If they push back, frame it as simplicity: “A lump sum is cleaner for both of us. Less paperwork, less back-and-forth, and I can allocate it where it’s needed most.”

12-month minimum severance with a relocation trigger. This is the big one. If you’re terminated within 24 months of relocating, your severance should reflect the fact that you didn’t just lose a job—you lost the entire infrastructure you built your life around.

Standard severance doesn’t account for that. A Displacement Premium does.

Push for 12 months minimum, and frame the relocation itself as the justification: “If this doesn’t work out for reasons outside my control, I’ll be unemployed in a city I moved to for this role. I need the runway to reflect that reality.”

90+ days of temporary housing. Most packages offer 30 to 60 days. That’s enough time to panic-buy a house you’ll regret. Ninety days gives you breathing room to make a decision that doesn’t compound the risk you’ve already taken.

Frame it as performance protection: “I’d rather spend my first three months focused on the business than racing to close on a house I haven’t had time to evaluate.”

Spousal career support. This one gets overlooked constantly—and it’s often the hidden deal-breaker. Your partner didn’t get recruited. They didn’t get a signing bonus. They got uprooted.

A formal spousal support provision—career coaching, job placement services, even a modest stipend to bridge the income gap during transition—signals that the company understands what relocation actually costs a family. And it removes the single biggest source of resentment that quietly erodes an executive’s commitment from the inside.

Cost-of-living adjustment. If you’re moving from Austin to New York, the math isn’t subtle. Income tax alone should be top of mind. But most executives absorb that delta silently because they don’t want to seem difficult.

Name it. Quantify it. And frame it not as a complaint but as alignment: “I want to make sure my effective compensation doesn’t decrease as a result of accepting this role. A COL adjustment keeps us aligned on the value of the package.”

Now—here’s the part that matters most against PE specifically.

You will not win any of these asks by out-smarting the firm.

Their comp team has more data than you. Their legal team has more precedent than you. Their operating partners have seen more negotiations than you.

You win by making the emotional cost of saying no higher than the financial cost of saying yes.

Every one of these asks should be framed around three principles:

Fairness. Not entitlement—fairness. There’s a difference. “I’m asking for what reflects the commitment you’re asking me to make” is a sentence most struggle to argue against, because arguing against it means explicitly stating that the commitment doesn’t matter.

Most people won’t say that out loud.

Reciprocity. You’re not demanding. You’re matching. “You’re asking me to take on meaningful personal risk. I’m asking for protections that reflect that risk.” This is mirroring at the structural level—the kind PE firms understand intuitively because their entire model is built on risk-adjusted returns.

You’re simply applying their own logic to your side of the table.

Future performance. Every ask ties back to your ability to deliver. Not “I deserve this.” Not “the market says this.” Instead: “this is what allows me to show up fully committed from day one without managing personal risk in the background.”

You’re giving them the ROI narrative they already think in.

The executive who walks into a PE-backed negotiation armed with comps and benchmarks gets benchmarked right back.

The executive who walks in with a clear articulation of the risk they’re absorbing—and a calm, specific set of protections that make that risk manageable—changes the texture of the conversation entirely.

One is a negotiation. The other is a realignment.

Final Thoughts

The relocation conversation is never really about the relocation.

It’s about whether you understand the game you’re walking into—or whether you’re just grateful to be invited.

Every executive I work with who has left six figures on the table previously did so for the same reason.

Not because they lacked leverage. Not because the company wouldn’t have paid it.

But because they didn’t recognize the moment for what it was—a window where their future employer needed them to say yes more than they needed the employer to say yes.

That window closes the moment you accept.

A Displacement Premium isn’t a line item. It’s a philosophy.

It’s the recognition that when a company asks you to move your life, they’re not asking for a change of address. They’re asking you to convert personal stability into institutional commitment—and that conversion has a price.

The executives who capture it aren’t necessarily better negotiators in the traditional sense.

They don’t have sharper elbows or louder voices—or aggressive tendencies. They have clarity about what’s being exchanged—and they name it before anyone else in the room does.

That’s the advantage.

If you’re in the middle of one of these conversations right now, here’s what I’d tell you:

Slow down.

The urgency you feel is manufactured—not by malice, but by process.

Companies move fast because momentum favors them. Your job is to interrupt that momentum just enough to have the conversation that protects you without derailing the deal.

Name the risk out loud. Not as a threat. Not as a complaint. As a fact.

“I’m relocating my family for this role, and I want us to structure this in a way that reflects that commitment.” That sentence costs you nothing and changes everything.

Negotiate the severance before you move—not after things go sideways.

The moment you’re in the new city, your leverage evaporates. Every month you spend in that role without protections is a month where the company’s flexibility grows and yours shrinks.

And remember: the company that won’t protect you on the way in is telling you exactly how they’ll treat you on the way out.

Next week, I’ll be diving into something that’s been gnawing at me—how AI is quietly creating the biggest talent divide we’ve seen in a generation, and what it means for how executives should be thinking about their careers right now.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

I have a confession to make.

I am incredibly impatient.

When I want something, I work my ass off, I reverse-engineer the path to get it, and I take it. That drive has built my businesses and provided for my family.

Many of the senior leaders I work with share this trait.

It’s also one of the reasons that we can see the pattern in others and why we often obsess about correcting courses to avoid costly mistakes for our clients and employers.

However, impatience has a dark side.

In the last five years, I have bought, traded in, or leased over 10 new cars.

In 2024, I cycled through four different BMWs.

Four. In twelve months.

That’s not intended to be a weirdly arrogant flex—rather—it’s quite embarrassing being the dad taking the top down on a BMW in a Tahoe snow storm so he can get his toddler out of the back seat.

I am—or at least have been—that belligerently obnoxious.

Yes, a car seat does fit in the back of an M8 - I don’t recommend it.

FWIW, now I drive a Silverado and a Suburban.

I prioritize what’s best for taking care of the household and comfort for the entire family over my gearhead neurosis.

But my lack of patience doesn’t stop at the garage. My family has moved 8 times in the last 10 years.

An ugly truth about my psychology?

The second I am not totally happy—the moment a hint of friction, discomfort, or boredom sets in—I make a change.

Probably another reason that I have been coined the guy you talk to for career transition work. I’m a big proponent of embracing change.

Perhaps it’s taking self-agency a bit too far—or simply a fear of avoiding the uncomfortable phases.

I buy a new car. I pack up the house. I change the scenery.

We can poke fun at how absolutely frivolous, wasteful, ridiculous, and privileged that all is—but I’d prefer to think of it as reinvention of self if only to protect my ego.

It is a dopamine hit disguised as a solution. It is childish. And it is unnecessarily risky financially.

Warren Buffet or Dave Ramsey or whoever today’s financial gurus are would slap me silly.

I’m sharing this embarrassing lack of impulse control to hold myself accountable. But more importantly, I’m sharing it because it’s the exact same psychological trap I see destroying the careers of the executives I advise.

When we feel friction in our roles, we want out yesterday. When we get a new job offer, we want to sign it immediately.

We treat our careers the way I treat my garage.

When we’re uncomfortable, we want the discomfort to end as soon as possible. But growth happens when we’re uncomfortable.

My car-buying habit is driven by restless boredom, but I know the urge to rush a career transition is driven by something much heavier: anxiety.

When we feel the friction of a toxic role or the vulnerability of a job hunt, our primitive brain screams for safety. But whether the root is a frivolous dopamine chase in a car lot or deep-seated fear in a boardroom, the result of impatience is exactly the same—we forfeit leverage.

Manufactured Urgency

We live in an era of “need it now” expectations.

Corporate America has trained us to measure our worth by our responsiveness. If you aren’t moving fast, you’re falling behind. Growth at any cost—charts up and to the right.

But in high-stakes career moves, haste doesn’t just equal risk. Haste actively destroys your power—and potentially deeper pain like fulfillment, happiness, and family.

The moment you let the clock dictate your actions, you tend to stop acting like a differentiated solution and often start acting like a commodity.

It’s one reason that it’s easier for many to find or negotiate for a better job while you’re already employed. Your needs are already being met and you have more ability to simply say no.

I learned much of my foundation on timing and urgency from the legendary negotiator Herb Cohen in his book, You Can Negotiate Anything.

Cohen taught us that time is a weapon.

The side that is sweating the deadline is the side that loses.

However, in the senior leadership arena, most urgency is manufactured.

When a recruiter says, “We need an answer by Friday,” or a hiring manager pushes for an accelerated start date, they weaponize time against you.

They know that urgency triggers your primitive brain.

It creates a scarcity mindset.

This pressure encourages you to bypass your strategic thinking and default to your biological need for safety and immediate gratification.

Appeasing this false urgency is the fastest way to leave money, title, and autonomy on the table.

When you rush into the next role just to escape the discomfort of your current transition (or the discomfort of negotiation in general), you aren’t negotiating against the company.

You are negotiating against your own anxiety.

What if instead, you began challenging the urgency?

• Why is that deadline there?

• What happens if that deadline is missed?

• What’s really at stake?

Asking a few simple follow up questions can help you better understand what the organization really values—and may give you new angles to explore how to “expand the pie” and collaborate on a stronger, more valuable (e.g, lucrative), solution for everyone involved.

Leaders Plan in Years; Panic Reacts in Days

When you are desperate to escape a bad role, you start measuring your life in days and weeks.

You just want the pain to stop.

But true leverage requires you to act like the senior leader you are.

You have to separate your immediate anxiety from your long-term strategy.

The strongest negotiators are the ones who have built the psychological runway to sit comfortably in the uncertainty of waiting.

Wealth, power, and leverage are built on the ability to delay gratification.

If you want to elevate your career, you have to expand your time horizon. You must decouple your ego from the dopamine hit of a fast offer or a quick exit.

Or that sexy Porsche 911.

True leverage is the ability to look at a “good” offer, recognize that it doesn’t align with your vision, and say no—or have the audacity to challenge what it would take to transform it from a no way to a no brainer.

It’s at that point that meaningful negotiation really begins. The point of muscle fatigue and uncertainty that stimulates growth for everyone involved.

The Power of the “Right” No

Saying no is a muscle.

Flexing it proves to yourself—and the market—that you are not desperate. Pricing and positioning yourself as a premium solution can have a similar effect.

For example, a high price signals that you’re okay with saying no to a larger audience that would work with you at a lower price.

To reclaim your power during a career transition or exit, you have to actively resist the temptation to act in haste.

You have to stop rushing a deal at the first sign of discomfort—even though being in a career transition, looking for a job, or schmoozing another networking event is akin to chewing glass.

Here are a few ideas the next time you find yourself in the heat of the muck.

• Call the Bluff on Deadlines: Artificial deadlines are designed to force concessions. When handed an exploding offer, try silence. They will come back to you prior to your response, often revealing key information that will help you negotiate better. If the offer vanishes because you took 48 hours to consult your family, it wasn’t a strategic fit—it was a trap.

• Embrace Strategic Delay: The longer you can stretch the conversation without killing it, the more invested the other side becomes—and the more time you have to develop strong alternative options. As their investment of time and energy grows, your leverage compounds. You also gain the opportunity to establish more scarcity for your time while communicating at a control cadence that better serves your needs.

Your ability to say “no” to an okay opportunity today is the only way to secure the right opportunity tomorrow.

There is a popular rule in business: “If it isn’t a hell yes, it’s a hell no.”

But in high-stakes career transitions, that rule only applies to the final outcome, not the starting line. When handed an okay offer, don’t just walk away—and definitely don’t cave in.

Use strategic delay to stretch the conversation. Challenge the constraints.

See if you can negotiate that “maybe” into a “hell yes” before you make your final call.

Finding Peace in the Garage

I am working hard on my own impulse control—especially because my boys need it to become honorable men—and I wish my parents had done that work with me.

I’m trying to learn how to sit in a house for more than a year without browsing Zillow at 2:00 AM to see if people have finally accepted that the market sucks. I’m trying to drive my truck without wondering what the new M3 drives like.

Fortunately, the new BMWs are so ugly, I don’t have to worry about the performance.

So long M8… and yeah, the license plate was NEGOT8. Cringe.

Because I know that every time I act in haste, I am trading long-term compounding value for a short-term hit of relief.

When you rush your career, you risk everything for the illusion of progress.

Stop appeasing the panic. Slow down. Expand your time horizon.

The moment you prove you don’t need the deal right now, you gain the power to write your own terms for the deal that actually matters.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Yeah, I really went through with it.

Permanent LinkedIn delete.

I took a stand against the FOMO and digital dogpiling described by most as, “a necessary evil.”

Are we sure it’s necessary?

Why?

Why are we so quick to describe LinkedIn as evil?

There must be a good reason. And you and I both know it.

I signed up for LinkedIn back in 2008. I ran a blog on Wordpress that I coined Career Ambitions.

Yeah, I’ve always been that nerd.

Photo of me on LinkedIn, blogging back in 2008.

Little did I know that my career ambitions would haunt the next 20 years of my life.

From 2008 to 2012, LinkedIn wasn’t a platform, it was a gold rush for a kid searching for meaning and direction. In those days, the “kid” ran social media because companies were told that they needed to be there, but weren’t really sure why.

I built my early career on that opportunity and “alignment.”

LinkedIn was part of the big 3 networks with Facebook and Twitter that corporate marketers would invest in. Snapchat, Pinterest and Instagram were still duking it out to see who would be the image dominant platform alongside them.

I spent my early 20s as a social media manager, then a content marketer, eventually climbing the ranks to VP of Marketing—all on the back of talking about it on the blue “In” icon.

For a kid who ran away from home, didn’t go to college, and worked graveyard shifts at Home Depot to get by, moving from $7.40 to $12 an hour to $35K a year — to $120K — to $250K in a 24 month period was absolutely mind blowing.

Me “forking around” at 2 or so AM at Home Depot in Auburn, California.

I was truly blessed to participate in the digital gold rush in Silicon Valley—and I give plenty of credit to timing and luck—although I look back at the wreckage with disdain.

Social media and publishing content pulled me out of the trenches of a white trash future—away from a world where the path was a 1/5th of liquor a night and a few bong rips—until I could afford something much stronger to dull the emotions.

In 2014 I took a contract social media and content role with Xerox which I negotiated to a Director of Marketing title with the VP.

I made the announcement on LinkedIn and within a week I was a 2015 Forbes 30 Under 30 finalist.

I had the most profile views of anyone at the company—outranking the others in the top 3—our CEO Ursula Burns and CMO John Kennedy.

Un-fricken-real.

That’s when I really started paying attention to the perception that LinkedIn can perpetuate—and others started paying attention too.

Again, just a kid reaching a few too many rungs up on the ladder, pacing with corporate giants—at least that’s how it was perceived because of LinkedIn.

In those days, the air was different. It felt like a genuine meritocracy—which is why my career was hyper accelerated with how public my work was.

You shared an insight, you connected with a leader, and doors opened.

It was a high-signal, high-trust, and high-reward platform.

LinkedIn was the foundation of everything I would eventually become.

By 2016, I had turned that obsession (and other’s interest in how some 12 year old looking kid found quasi-online fame) into my first real business with a P&L, employees, and equity considerations.

I launched Discover Podium—on LinkedIn of course.

The codependency and obsession grew concrete.

We scaled to over a million the first year—largely working the LinkedIn ecosystem.

But I have to be honest.

I wasn’t a victim of this system; I was one of its architects.

At Discover Podium, we didn’t just ‘polish’ the C-suite—we helped build the very ‘performative professionalism’ I’m now complaining about. We rewrote profiles, ghostwrote updates, and manufactured authority for leaders at Fortune 500 companies

We taught people how to hack the algorithm and prioritize ‘reach’ and we helped job seekers land faster by reverse engineering the LinkedIn Recruiter system.

We even acted as executive agents so senior leaders wouldn’t even have to get their hands dirty.

It’s one of the reasons that I tore the business apart instead of selling it in 2020. It felt gross and disingenuous—plus it was a workaholics hellscape.

I helped build the noise, and for that, I take my share of the blame.

Others wanted to have what I had—and I had seemingly had the formula.

But there was a hidden tax. I just didn’t see it when I was 27.

At the peak, I was personally closing $40K a week—which at the time could have been anywhere from 20-60 high velocity sales deals. I was leading a team of 25 people and building systems so the sales team could follow my performance.

And behind closed doors I was a prisoner to the system.

I remember the ritual.

I’d wake up at 3:00 AM to pee, and before I even hit the light switch, I was refreshing the LinkedIn ProFinder feed to send proposals and keep my calendar booked like a desperate BDR.

I was sifting through 250 leads a day in San Francisco alone—my team replicated the effort in New York, Seattle, Denver, Chicago, etc.

That meant I also set unfair expectations for their work as well.

If I didn’t refresh the screen with that familiar finger pop—if I didn’t hunt for those dollars in the dead of night—the machine didn’t eat.

My team wouldn’t get paid.

I did this for 5 years—let me repeat, 5 f*ck’n years—to keep my calendar locked down with 10-15 calls with senior leaders every day—and I cosplayed as the CEO between it all.

I struggle with an addictive personality. It’s a great strength and dangerous liability.

If you’re on the side of hustle culture, you may say, “HELL YA BRAH!”
If you’re on the side of balance, you might decry, “Lunatic.”

I bet that some of you reading this know precisely how it feels.

Through it all, I sold millions of dollars on LinkedIn. I built a following of 35,000 people. I spent nearly two decades treating LinkedIn as the center of my professional universe.

It’s provided for me and my family—and the many others that have worked for me.

It also taxed the hell out of my central nervous system.

But the “heyday” of Linkedin is long behind us.

The tool that built my house has become the poison in the well.

I don’t share all this as a roundabout humble brag, I share this for context of how entwined my life has become with LinkedIn—and many of you are likely just as stuck for your own reasons.

Failure of the Feed

A few years ago, the data started telling me a story that didn’t bode well for keeping LinkedIn in my life. But I’ve been scared to take it seriously, because what if someone can’t find me?

I looked at my revenue for the last six years as a solo operator.

As I audited the sources of my revenue—the truth is that LinkedIn and professional communities contributed essentially nothing—while dominating about 80% of my energy.

My word-of-mouth referrals and direct relationships generate 10x the revenue of anything I’ve picked up on LinkedIn in the recent years.

My primary target audience—the leaders making a $1M to $5M+ W2 year—don’t spend their afternoons arguing in comment sections.

They don’t have time to “engage” with my latest poll.

They are busy leading the world. And I’ve found that many of them have PR firms running their accounts.

By staying on the platform, I was marketing to a crowd that was increasingly “low-fit” while ignoring the high-trust relationships that sustain my life.

Further, I’m inundated with noise or advice on how I should be—from people I’m not trying to attract.

I’m probably in the wrong room. But everyone is in the same room—right?

I’m not suggesting that I’m ungrateful or that I’m better than LinkedIn frequenters—I’m just suggesting that if you listen to the wrong signal, you become further distracted and confused about your purpose.

Since having children, I really don’t have time to be all things to all people—and expect to be the spiritual leader of my home, a loving husband, and role model for my boys.

But yes, if you cheapen my intent, it sounds like, “If you don’t make a million plus your opinion doesn’t matter to me.”

Honestly, run with this how you will.

The Low-Signal Trap

LinkedIn has become a feed where we perform “professionalism.”

It’s a middle-school cafeteria for people in suits, parody accounts built by trolls, and the highest level AI slop disguised as insight. I’ve heard that other platforms are like this too. That social media as we know it is done for.

Good riddance.

It’s easy for me to call it a ‘trap’ now that I’ve reached meaningful enough revenue to support my family and lifestyle without it.

I recognize the irony in criticizing a platform that gave a kid from Home Depot a voice.

Yeah, that kid. Cringe.

For many, that ‘noise’ is the sound of opportunity.

My frustration isn’t with the people trying to find their way; it’s with the environment that forces them to perform a persona just to be seen.

And furthermore, it’s only becoming harder for them to be seen.

The “meritocracy” I found in 2008 has been replaced by a race to the bottom of the “Agree?” post.

The “noise” is now given the same volume as the “signal.”

Worse, the cost of participation has become an all-out assault on your peace of mind.

The algorithm rewards the contrarians and provocateurs—which has served me well—but you’re also broadcasting to swaths of people with hyper fragile egos and hairline triggers to scream their victimhood.

A single word—such as “mercenary” can inflame a counter-movement and devolve into mansplaining that spreads across LinkedIn, Slack communities, and Reddit—where digital dogpiling helps thousands of faceless anons feel empowered all while collectively waving their fists at absolutely nothing of importance.

It is the “unhealthy” inverse of LinkedIn’s toxic positivity—a race to dehumanize.

These threads quickly devolve from critiquing a post or comment to dismantling a person, fueled by an “Outrage Loop” where users are rewarded for finding the most malicious interpretation possible.

How convenient.

What’s most jarring is that LinkedIn has begun to mirror the worst parts of Reddit—the digital dogpiling and the rush to ‘main-character’ someone for a few thousand likes.

But on LinkedIn, it’s happening without the veil of anonymity.

People are dismantling careers and reputations under their own names, often for the sake of performative virtue.

To me, that’s not just toxic; it’s dangerous.

We’ve turned a networking site into a surveillance state where the cost of being human is a public trial.

There’s no room for nuance, only performative cynicism, where the mob competes to see who can be the most “above it all” until they become just as insufferable as the people they’re mocking.

I’ve had my entire afternoon soured by mindless, snarky comments from 2nd and 3rd degree LinkedIn members multiple degrees removed from my ICP—folks who don’t know a lick about me or my mission.

And why?

Because I’m just as addicted, guilty, and tuned in as them.

On LinkedIn, their “hot take” is treated with the same weight as my life’s work.

And if you try to be human?

If you share a raw truth outside the “humbled and honored” script?

You risk being screenshotted, stripped of context, and fed to the wolves on r/LinkedInLunatics so a bunch of veiled critics on Reddit can feel superior for five minutes.

We’ve traded the boardroom for a digital coliseum.

We have cheapened everything about our corporate experience to this. I’m simply opting out from getting mauled just to feed an algorithm.

To be clear, when I talk about ‘low-fit’ signals, I’m not talking about human value—I’m talking about focus.

I spent years chasing ‘likes’ from people who would never hire me, while too-often ignoring the deep work required for those who would.

I let my ego be fed by junk volume when my soul needed depth.

That’s a failure of my own strategy, not the fault of the people engaging with me.

The Trade I No Longer Make

My oldest son turned three on Tuesday.

It hit me hard. Parents reading this know exactly what I mean.

I will never have the opportunity to play with my two-year-old again.

NEVER.

That version of him is gone.

His gravity defying baby curls have been replaced with bristly blonde little boy hair.

He’s not a baby. He’s a boy.

And soon he will be a man. What will he think about when he thinks of his father?

Will he remember my face at night, lit from blue light, wearing a frown because some anonymous nobody stole my attention from him?

Or will he remember that my eyes are green, that my face always lights up when I see him, and that my soul is lighter and full of love in his presence?

And looking back, I can see the moments I missed because I was mentally miles away—stuck in a digital argument with someone I’ll never meet.

Someone whose opinion of me only takes joy away from my family and provides nothing of substance.

Someone who is outraged for nothing.

I’ve spent too many evenings at 7:47 PM, when I should have been present and focused on my family, feeling the slow burn of “hate mail” in my gut.

It’s my boys’ bedtime routine—not the time to ruminate over some word choice I used on a throwaway comment that I didn’t triple check to make sure I didn’t trigger or offend another person.

I’ve allowed myself to get sidetracked by others who can take a single word or sentence of mine and turn it into their personal punching bag for the day.

Is that really the best use of your time? As an executive leader in title only?

I too often let people who don’t know my name, my family, or my story—dictate the mood of my home.

How weak have I become?

I used to think my ‘always-on’ nature was a competitive advantage.

It wasn’t.

It was a boundary issue.

I wasn’t ‘weak’ for being addicted; I was human, caught in a feedback loop designed by the smartest engineers on earth to keep me there. And some of which—ironically—I helped get hired at LinkedIn.

Reclaiming my attention isn’t just about deleting an app—it’s about admitting I can’t win a war against an algorithm while trying to be a present father.

We talk about social media being “free,” but that’s a lie. We pay for it with our nervous systems.

We are the product that big tech monopolizes. But let’s keep throwing those dollars in the big tech ETFs and pretend to be surprised.

Necessary evil? Devil in disguise?

No, these demons are out in the open—they don’t need to hide anymore.

They’ve got us by the short and curlies—or the golden handcuffs if you prefer a less crass simile.

I’ve spent nearly two decades training my brain to be “on” at all times.

I thought it was a competitive advantage—and perhaps it was for a time.

I thought that being the guy who could catch a lead at 3:00 AM or deflect a troll at 8:00 PM was what made me successful.

It didn’t make me successful. It just made me tired.

It creates this constant, low-level static in the back of your head. You aren’t “checking” LinkedIn; you’re monitoring your status. You’re waiting for the next hit of validation or the next spark of conflict.

And while you’re monitoring that screen, you’re missing the real life happening three feet away from you.

Reclaiming the Signal

I’m a strategist, and I realize that I too often mismanage my most important asset: my attention.

The math doesn’t work.

I recognize the immense privilege in being able to hit ‘delete.’

For a freelancer starting out or a mid-career manager looking for a lifeline, the noise isn’t a nuisance—it’s a necessity. I’m not pathologizing the hustle; I’m simply admitting that I’ve reached a point where I can finally afford to stop shouting into the void, and I’m choosing to take it.

If 90% of my business comes from high-trust referrals and real-world relationships, why am I giving any of my mental energy to a feed full of noise and AI-generated “insights”?

I’ve realized that I don’t need “reach.” I need depth.

Funny enough, while being featured on LinkedIn Lunatics—I concurrently closed a deal that nets over a half a million in success fees within a dozen hours of highly tuned-in guidance.

It’s like God said, “Seriously? Can I make this anymore clear for you?”

I don’t share that number to flex, but to illustrate a strategic epiphany: the ‘clout’ and the ‘cash’ had become completely decoupled.

The digital coliseum is a distraction from the value I provide.

Maybe it is for many of you too.

That deal was the final proof I needed that my presence on the feed wasn’t load-bearing—it was just a vanity project that was costing me my sanity.

The people who matter most to my career have my phone number and I’m in frequent contact with them to remain enough top of mind.

They don’t need to see my “thought leadership” in their feed to know I deliver.

And the people who do need to see it are usually the ones making the most noise for the least amount of value.

I’m opting out of the “reach” game. I’m choosing to go where the signal is clear—my family, my actual clients, and my own peace of mind.

And for those of you making bets about when I get LinkedIn back—please give me a break.

Why do you hope I fail—even if in jest?

Does it make you feel better about your choices?

For those telling me to leave it on hibernate, simply uninstall LinkedIn from your phone, or just keep a landing page with the followers and all the clout—I can’t do that.

That’s like asking an alcoholic to put the poison on the top shelf.

I know how to get a ladder.

So I opted for permanent delete.

This Is Not a Recommendation

I am not telling you to follow me.

I’m not suggesting that you delete your profile or that LinkedIn can’t still be a tool for your career or business. I’m simply giving you the data on why I finally decided to cut the cord.

This was my math.

For me, the “Necessary Evil” was no longer necessary. It was just evil.

It’s been one week since I hit the button. My phone is quieter. Every other social channel is gone, too. No Instagram, no Twitter, no Facebook, no noise.

I am off grid.

The iMessage and email notifications continue at a hot pace—I can live with 2 channels for now.

And for the first time in twenty years, the “static” in my head is dissipating.

I’d be lying if I said it was gone or if I wasn’t nervous—check back with me in 6 months. If I write a “I regret everything I said about LinkedIn, please come follow me again” post, please recommend a good psychiatrist.

My son turned 3—and I didn’t check LinkedIn. Damn that feels good to say.

I’ll continue to write this newsletter because I believe in the long-form exchange of ideas. I believe in depth. But I am watching the horizon.

The difference here is the ‘contract.’

A newsletter is a handshake; a feed is a slot machine.

I’m trading an algorithm-driven ‘reach’ for an opt-in relationship. I’d rather speak to 500 people who want to be in the room than 35,000 who are just passing by the scene of a wreck.

If Substack eventually devolves into the same social contagion—if it becomes a place of performative outrage and “Agree?” threads—which I suspect it will—I will leave it behind too.

I will migrate this newsletter to a broadcast-only channel.

I have concerns with their notes feature. I have been playing with it—and it does trigger some AI slop and wildly inane nonsense—I may need to cut ties sooner than I’d hope.

I care about the people who are in the room with me.

I enjoy debate and criticism in good faith. I’m not looking for a gotcha moment to dismantle you publicly. And I do appreciate the redirections, considerations, and opportunities to learn from others.

I care about the results I deliver for my clients.

And I care about being the man my sons deserve to have as a father.

Plus, and I know new dads understand this, I need to find more time to care for my wife. We’re both so much in the trenches that it’s hard to find time for each other.

At least I can say, LinkedIn won’t be sapping what little time I have to share anymore.

I think we all fantasize about a more analog world again—perhaps it’s nostalgia—or perhaps we know we’re very well stuck in what we’ve created. The ultimate bait and switch to monetize our attention.

If you’re waiting for me to come back, don’t hold your breath.

I’m not looking for a ladder to get back to the poison. I’m not looking for an ‘NA’ alternative.

I’m walking away from the shelf entirely.

I’m not here to play the ‘reformed addict’ who judges everyone still at the bar.

If LinkedIn is a tool that works for you without costing you your peace, stay and win.

But for me, the relationship became purely transactional and emotionally expensive.

I’m not leaving because I’m ‘above’ the platform; I’m leaving because I no longer like who I am when I’m on it.

Stay Fearless

The world won’t end because you stop posting.

In fact, your real life might finally begin.

I’m going back to the work that matters most.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Most people walk into an interview and immediately lower their status—even the most prominent senior leaders.

They sit down, fold their hands, and enter a subservient state.

They wait to be asked questions.

They hope to be picked.

They treat the company like a benevolent benefactor and themselves like a lucky recipient.

This is a signal of weakness.

When you act subservient, the hiring manager’s brain immediately devalues you.

Humans assess social hierarchy in milliseconds.

If you signal that you are “lower” status, the interviewer categorizes you as a commodity to be bought at the lowest price, not an asset to be acquired for growth.

You must flip the dynamic.

You are not there to simply answer questions about your past.

You are there to perform due diligence on the opportunity ahead.

You are trading your most finite resources—your time, your cognitive load, and your reputation—for their equity and salary.

If you don’t audit the opportunity to the best of your ability, you are gambling with your career.

Below are 27 “offensive” questions designed to test the reality of the company, expose toxic leadership, and demonstrate that you are a peer, not a subordinate. The last 5 are borderline insane asks—but I’ve seen it all.

Forward this to inspire a friend who is interviewing this week.

Category 1: Strategic Clarity

The Goal: Determine if the ship is growing, steering, or sinking.

Too many leaders operate in a state of reactive panic. They are putting out fires and lack a coherent vision. They will never admit this to you in a standard interview.

You have to drag it out of them.

1. “If we are sitting here one year from today celebrating a massive win, what specifically did we achieve?”

This forces them to define success with metrics, not feelings.

If they give you a vague answer (“We want to grow,” “We want to disrupt”), it means they don’t know where the goalposts are.

Note: Be especially mindful if your compensation is tied to undefined performance goals.

2. “What is the one strategic threat that keeps everyone on edge that you haven’t told me about yet?”

By asking for the “threat,” you signal that you are strong enough to handle the truth. A secure leader will respect this. An insecure leader will pretend everything is perfect.

Bonus points if you can predict the threat based on your experience and help them solve it right then and there—solve their future, don’t explain your past.

3. “If this role fails, what will have been the structural cause(s)?”

• Script A (Weak): “What are the challenges?”

• Script B (Strong): “What is the structural cause of failure?”

“Challenges” invites them to talk about your lack of skill.

“Structural cause” forces them to audit their lack of support. This separates personal failure from organizational incompetence.

4. “How do you make decisions when you don’t have enough data?”

Executive leadership is rarely about 100% certainty; it’s about probability.

This reveals their cognitive processing style. Do they freeze (analysis paralysis)? Do they shoot from the hip (impulsive)? Or do they have a framework?

5. “What is the biggest decision you made in the last 6 months that you regret?”

You are testing for their ability to take ownership and adapt. If a leader cannot name a regret, they may suffer from ego-lock. They may blame you for their mistakes later.

6. “Who holds you accountable?”

This is the boldest question.

In toxic hierarchies, the CEO or VP is a feudal lord with no oversight. In high-performance cultures, everyone answers to a metric or a board. Watch their body language when you ask this. If they flinch, you found the ego.

Remember: Everyone wears their Sunday best during the interview process. It’s your job to expose where the dirty laundry is—so you don’t end up laying it in later.

Read more

Picture this.

You are in a stressful board meeting or ELT discussion. The air in the room is thin.

Yeah, even the air in your home office becomes scarce.

Suddenly, a complex question lands—seemingly hair brained and off topic.

It’s specific. It’s technical. And you have absolutely no idea what the answer is.

Your pulse quickens.

You feel the heat rising up your neck. The silence stretches, and in that split second, your brain screams at you:

Fix it.

You feel a need to prove you belong in the room. So, you start talking.

• “That’s something we can certainly align on...”

• “We have a framework for that...”

• “I’m confident we can handle that complexity...”

You didn’t lie, exactly. But you didn’t tell the truth.

You bluffed. You bought yourself time to panic later. You filled the dead air with corporate noise because silence can feel like failure.

This is a mistake.

It’s called the Expert Trap.

As a consultant, I have fallen into this a few more times than I care to admit. And even after over 30,000 conversations with senior leaders—I am still learning every single day.

The Expert Trap is the belief that leadership is a performance art where you must have a quick, clever answer for every problem. I suspect it’s more unconscious bias than actively trying to one up everyone else.

But when you fake an answer, or fill the room with corporate speak—you do three dangerous things:

1. You cap your upside. You often agree to terms or timelines you don’t fully understand.

2. You destroy your leverage. You are no longer assessing the deal; you are now defending a position that was just made up on the fly.

3. You signal weakness. Your urgency can be perceived as desperation or submissiveness.

Most executives think they need all the answers to win.

Wrong.

In complex negotiations, the person pretending to know everything is usually the weakest link.

The one that has it all figured out—with utmost certainty—is the one most blinded to getting creative, building stronger and more collaborative outcomes, and most likely to fall trap to precedents, benchmarks, and the way it’s always been done.

The person asking the questions is the one in control.

And you can tell if a senior leader is worth their salt by the quality of questions that they ask and how much extreme ownership of their failures that they claim. We’ll save that topic for another article.

Your goal is never to prove how smart you are.

It’s to get the best outcome for as many people as possible. And sometimes, the smartest move you can make is to look the other person in the eye and admit you don’t know exactly how to do it.

The Leverage Shift

Think about the mechanics of each high-stakes conversation you have.

There is a currency in the room: Information.

The person speaking is the person spending that currency.

They are revealing their position, their constraints, and their logic. The person listening—and asking questions—is the one collecting it.

When you rush to answer a question you don’t understand, you are voluntarily handing over your leverage. You are “spending” credibility you don’t have to defend a position you don’t fully understand.

The moment you decide to push out any answer to fill dead air, you stop listening to understand and start listening to survive.

You more easily miss the subtle cues, the hesitation in their voice, or the gap in their logic that could have won you a better deal.

Note: Leverage here doesn’t mean domination. It means clarity. When you rush to answer, you are often fighting the other person. When you ask the right question, you are teaming up with them to fight the problem.

Interview processes are notorious for this because the nature of each conversation feels like YOU are on display and have something to prove—when in reality, it should feel more like a two way evaluation of respect, value exchange, and collaboration.

Strategic ignorance flips this dynamic in these scenarios.

When you pause and say, “I don’t know,” or “Can you walk me through that?” you force the other side to do more heavy lifting.

1. You expose the cracks. Often, when you ask someone to explain a complex detail, they realize they don’t fully understand it either. Or, they reveal a constraint they were trying to gloss over.

2. You buy time. While they are busy explaining, you are busy thinking. You get to process the new information without the pressure of performance.

3. You build trust. In a corporate world full of people pretending to be experts, admission of ignorance is disarming. If you are honest about what you don’t know, they will believe you implicitly when you tell them what you do know.

The “Expert” tries to impress the room. The Strategist works to understand it.

The Exception: Distinguish between data and direction. If you don’t know your current revenue or headcount, you aren’t being strategic; you’re unprepared. Strategic ignorance is for solving complex, non-binary problems—not for dodging basic homework.

Read more

From 2000 to 2003, basketball wasn’t a hobby for me.

It was oxygen.

I was the kid wearing And1s, obsessed with Allen Iverson’s crossover, trying to carry that grit onto the asphalt.

I spent hundreds of hours on my PS2 mastering NBA Street Vol. 2, and thousands more in my backyard, jumping until my legs burned, desperate to add a single inch to my vertical.

It didn’t happen, but I digress.

Basketball was my escape from the reality of childhood trauma—and I was impressionable and desperate for a male idol.

At the center of my universe was Kobe Bryant.

I was a diehard Lakers fan living deep in Northern California—hostile territory.

When Robert Horry hit that dagger three in Game 4 of the 2002 Western Conference Finals, I walked into class the next day in my Kobe jersey, ready for war. I mocked my classmates. I collected Kobe rookie cards (I still have them).

Yeah I’m not proud of it.

I didn’t just watch Kobe. I loved Kobe.

Then came the summer of 2003.

Eagle, Colorado.

I watched the trial updates religiously. I remember the knot in my stomach. I prayed for his innocence because if he wasn’t innocent, then the model I had built my life around was tainted.

Then the details came out. The admitted adultery. The settlement. The diamond ring apology press conference.

What really happened?

I guess we can only speculate—though the bruising suggests otherwise. Part of me wonders if we’d have a different outcome if this happened during the #metoo era.

I still get sick thinking about it.

Feigning ignorance is no excuse for alleged rape.

And let’s say you are innocent—a $4 million dollar apology ring doesn’t change the fact that you barely made it two years into marriage without cheating on your wife—though you openly admitted to other indiscretions too.

And then, I watched the greatest magic trick in sports history.

Whether Kobe used this as a survival mechanism or a performance hack is up for debate—but the way Corporate America adopted it is undeniably toxic

Imagine that.

Kobe openly admitted that he created “The Black Mamba” alter ego to handle the backlash of the sexual assault case.

He killed the accused rapist and replaced him with a superhero.

And everyone simply turned the other cheek—as we often will.

And it worked.

The Corporate Hall Pass

Corporate America didn’t just watch the magic trick; they copied it.

Walk into a high-growth startup or a sales bullpen and you’ll inevitably hear “Mamba Mentality” quoted as scripture or intense Kobe posters used in the backdrop for a Zoom call.

Why?

Because we love winners more than we value character.

But more importantly, we idolize the “ruthless competitor” because it gives us permission to be sociopathic in the pursuit of revenue. The water is full of sharks, and eventually, everyone bleeds.

What’s more frustrating is that the behavior is celebrated.

Perhaps I’m jaded from my recent work helping several executives navigate hostile PE takeovers and vengeful nepotism. I’ve watched good leaders get pushed around, chewed up, and spat out.

It seems this toxic 'it’s not personal, it’s business' mentality is rampant.

And this so-called Mamba Mentality keeps resurfacing.

It is the ultimate Hall Pass.

• If you yell at your team, you aren’t abusive; you’re “intense.”

• If you neglect your family to close a deal, you aren’t an absentee parent; you’re “dedicated.”

• If you bulldoze your peers, you aren’t a jerk; you have a “killer instinct.”

We look at the rings, the points, and the “dominance,” and we decide that character flaws don’t matter as long as the stock price goes up.

If you’re a tyrant, don’t admit it—rebrand it.

In the boardroom, we call this the ‘Competence Immunity.’

If a sales VP is hitting 150% of their quota, HR looks the other way when they scream at an assistant. If a founder raises a Series B, the board ignores the massive turnover and burnout rates.

We have decided that ‘High Performance’ is a solvent that washes away toxic behavior.

But this is a short-term trick.

You might respect the rings, and you might respect the revenue.

But ask yourself: Would you want your son to treat his spouse the way your top performer treats their team? Would you want your daughter to accept ‘greatness’ as an excuse for betrayal?

If the answer is no, then why do we accept it on our cap tables?

The Biology of “Fake” Strength

We need to name this behavior accurately. In psychology, this isn’t called “excellence.”

It is called Dissociation.

The human brain has two distinct modes of operation:

1. The Task Positive Network (TPN): Used for problem-solving and execution.

2. The Default Mode Network (DMN): Used for empathy, social connection, and reflection.

Neuroscience shows these two networks are antagonistic—when one is on, the other is off. You cannot be hyper-fixated on a task and deeply empathetic at the same time.

The strongest senior leaders will switch back and forth between networks rapidly. While we can’t do both simultaneously, the “Mamba” error is the refusal to switch back, effectively atrophying the empathy muscle.

Kobe created the persona to survive the trauma of his own making. He needed to separate from “Kobe the husband/defendant” to become “Mamba the assassin.”

I fear many of our peers in the C-Suite have done the same.

When executives adopt this persona, they aren’t channeling greatness. They are choosing to numb their humanity.

They are turning off the part of their brain responsible for guilt so they can drive their teams into the ground—and profits through the roof—without feeling the impact.

And we wonder why Millenials, Gen Z, and Alpha are quick to do anything they can to escape these very public—but seldom acknowledged—corporate smoke and mirrors.

The “Boos Don’t Block Dunks” Fallacy

The most dangerous tool in this dissociation toolkit is a single, catchy phrase: “Boos don’t block dunks.”

I have heard this—or a variation—of this quote more times from executive leaders than I’d care to count. On the surface, it sounds stoic. It sounds like “focus.”

But in reality, it is a psychological shield.

It frames Accountability as Opposition.

It convinces a leader that valid criticism regarding culture, ethics, or burnout isn’t “feedback”—it’s just “noise” from people who want to see you fail.

It allows them to act like tyrants because it categorizes all dissent as “hating.”

Guess we see this in politics as well—but with global implications.

This is a failure of intelligence.

In any other context, if the market screams that your strategy is failing, you listen.

You pivot. You fix the product.

But when the “Mamba” leader hears the market (their employees, their spouses, their children) screaming that something is broken, they simply turn up the volume on their own ego.

• “Boos” from your team mean your culture is eroding.

• “Boos” from your family mean your relationships are in default.

When you adopt the stance that “lions don’t lose sleep over the opinions of sheep,” you sever your feedback loops. You are flying the plane with the instrument panel turned off.

To be honest, I’m guilty of this mentality as well—especially recently when getting backlash that I think is honestly beneath me.

But hey, I can be an asshole too.

You might hit your Q4 numbers. But eventually, you will crash. And unlike Kobe, you likely won’t have the PR machine to spin the wreckage into a legacy.

Let’s be clear: The discipline is real. The 4:00 AM wake-up calls, the thousands of made jumpers, the obsessive study of game film—that is a feature, not a bug.

We should all aspire to that level of mastery in our craft—and I suspect that is exactly what these leaders choose to concentrate on. That is admirable.

But we must stop conflating Professional Discipline with Personal Immunity.

Being the hardest worker in the room buys you success. It does not buy you a pass on basic human decency.

We too often accept a false social contract that says if your output is high enough, your character requirements are lowered.

That isn’t ‘focus.’

That is a transaction. And it’s a bad one.

I’m not saying you’re a jerk if you love Mamba Mentality—I think you aspire for habit, discipline, and growth—rather, I’m saying that I can’t unknow what I know about where it came from—and I can’t look the other way.

Integrating The Whole Human Asset

So, where do we go from here?

Do we abandon excellence? Do we stop trying to win?

No.

But we must stop confusing Dissociation with Leadership.

Real power isn’t about creating an alter ego to escape accountability. It is about Integration. It is about managing the whole human asset—shadow and all.

We have to move from the “Mamba” script (Script A) to the “Integrated” script (Script B).

Script A: The “Mamba” Leader (Dissociated)

• The Context: A high-performer says they are burning out and the timeline is unrealistic.

• The Response: “We don’t complain here. If you can’t handle the pressure, maybe this isn’t the seat for you. We need killers.”

• The Outcome: You trigger their biological threat response. They shut down, work from fear, and eventually quit, taking their institutional knowledge with them. You have burned the asset to hit a short-term metric.

Script B: The Integrated Leader (Connected)

• The Context: Same scenario.

• The Response: “I hear you. The timeline is aggressive because the market demand is real. But burning you out isn’t my intention. Let’s look at the workflow—what can we pause or delegate so you can hit this target without breaking the engine?”

• The Outcome: You validate their biology. You lower their Cortisol. You retain the talent and solve the structural problem.

Script A feels stronger in the moment. It gives you a rush of dominance.

Script B is actually stronger. It creates sustainable leverage.

We don't need to kill the Mamba to save the Man. We need to harness the Mamba for the Man.

You must control it.

Keep the grit. Keep the obsession to detail. Keep the refusal to accept mediocrity. But decouple it from the idea that you must be a lone wolf or a tyrant to wield it.

True greatness isn’t achieving perfection at the cost of your humanity. True greatness is achieving perfection because your humanity is intact.

You can be a killer on the court and a faithful partner at home. You can be a ruthless competitor in the market and a supportive leader in the office.

The lie isn’t the work ethic.

The lie is that you have to sell your soul to maintain it.

Stop Worshipping the Mask

I still have the cards. I still remember the feeling of those And1s on the pavement. But I can no longer separate the player from the person.

“Mamba Mentality” isn’t a leadership philosophy.

It is a trauma response branded by Nike.

It is the sound of a man running away from himself.

As a father of two boys who will soon be men amongst us—I can’t tolerate this. I must lead my family and stand up—not hide behind the fact that most people won’t notice when your integrity slips.

Every time an executive quotes Kobe—or Jobs—or idolizes the companies eroding our humanity—to justify burning out their team or acting like a tyrant, they aren’t channeling greatness.

They’re just proving that, like 13-year-old me, they prefer the beautiful lie to the ugly truth.

Winning a championship (or a Q4 target) means nothing if you have to dehumanize yourself and our greater community to get there.

Stop worshipping the alter ego. Start demanding the whole human.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Last October, I advised a client who moved an offer from a $1.2M annual package to $1.9M in a single phone call—then we finished the deal at $2.2M.

When I shared that wins like this are possible on LinkedIn, the reaction from the recruiting industry was visceral.

My post was simple:

Companies disclose a range.

Often they hold back 20-40% more for candidates who prove exceptional value.

That disclosed range?

It's for people who negotiate like everyone else.

Don't be everyone else.

One executive recruiter commented:

“NFW (No F’ing Way). That is impossible.”

I guess they weren’t lying. To them, it is impossible.

Because to a recruiter, you are a line item.

But to a business, you are capital.

If you don’t understand the difference, you will leave 40% of your value on the table time and time again.

And remember, your mistakes compound throughout your career.

You Are Negotiating with the Wrong Department

To understand why salary bands feel rigid, you have to understand the incentives of the person you are talking to.

Most candidates spend their energy trying to convince a recruiter to pay them more. This is like trying to convince a cashier to lower the price of a steak.

They don’t have the authority, and asking them just annoys them.

Many recruiters manage OpEx (Operating Expense). Their metrics are:

• Time-to-Fill: Speed trumps fit.

• Cost-Per-Hire: Cheaper trumps better.

• Process Compliance: Safety trumps potential.

When an OpEx recruiter looks at you, they do not see an asset that generates revenue.

They see inventory.

They are incentivized to treat you like office furniture—get the best functional utility for the best possible price.

Hiring Managers manage CapEx (Capital Expenditure). The P&L Owner—and elite headhunters—operate in a different reality. They are judged on ROI.

• Impact: Will this person make me money?

• Speed to Value: Can they solve my $100M problem now?

The Disconnect: You are trying to sell a high-yield, complex asset to a person who is only authorized to buy paperclips.

Of course they say “No.”

They lack the authorization—and the vision—to say “Yes.”

You’re barking up the wrong tree, and it’s costly.

The “Budget” Is a Zombie Number

This brings us to the lie that kills too many negotiations:

“We don’t have the budget.”

Top senior leaders understand a fundamental truth of corporate finance: The “Maximum Approved Budget” is almost never the “Maximum Available Capital".”

The “Budget” is a zombie number.

It is often a placeholder assumption made by Finance six months ago, based on outdated market data and conservative estimates.

“Capital,” on the other hand, is liquid power.

It is a resource available to solve urgent, expensive problems now.

When a recruiter tells you “We don’t have the budget,” they may be blind to the larger P&L. They see the line item; they don’t see the liquidity pool reserved for emergencies and opportunities.

If you solve a $100M problem, a $1M compensation difference is a rounding error to the P&L owner.

But to the recruiter, it is a compliance violation. There are no benchmarks to prove that paying you a million more is competitive.

Good—this is what being differentiated feels like.

The trick is finding the big expensive problem that only you can solve—and aligning all of your narrative, timing, and expertise to maximize your leverage to take advantage of it.

If you can do this…

Stop negotiating with the person paid to save pennies.

Start negotiating with the person who needs to make millions.

Read more

You are scrolling LinkedIn at 11:00 PM, crafting the perfect post about your top “leadership lessons.”

This one is sure to be a hit.

You optimize the hook, check the engagement metrics, and hope the algorithm blesses you with visibility.

Meanwhile, the executive who just landed the role you wanted hasn’t posted in six months.

They are invisible on the feed.

But before the role was even posted, the hiring manager heard from three people. They told the recruiter: “Pay attention to this candidate.”

The recruiter back channeled a half dozen other leaders to prove they’d done their homework—and everyone said the exact same thing, word for word.

Most executives operate under a false assumption.

They think they have a marketing problem.

• “I need to post more.”

• “I need a better personal brand.”

• “I need more visibility.”

If this is you—you’re wrong.

You don’t have a marketing problem, you have a sales problem.

Most of us struggle to sell ourselves. That ends now.

Let’s define the difference:

The way that most people think about marketing is akin to casting a wide net and shouting into a void, hoping someone hears you.

Whereas sales is understanding that you need to develop internal champions and equip specific people to close deals on your behalf when you aren’t in the room.

If you are relying on posting to get hired, you are playing the lottery.

Top senior leaders don’t play the lottery. They build a distribution network.

This is exactly how I run my business. I’ll be transparent about how I run ThinkWarwick Global.

Outsiders will say it’s a word-of-mouth operation—how much of that do you think I orchestrate?

When you speak with 10-15 senior leaders everyday for a decade plus, you don’t need to run ads. You don’t even need a website. Hell, I probably don’t even need LinkedIn anymore, but I just can’t quit you baby.

I don’t “market” in the traditional sense.

I started this newsletter to build clarity of thought for client challenges I was facing. I do my best thinking while writing.

Sharing that publicly built a following.

But here’s what most people miss. The newsletter and 30,000+ followers on LinkedIn does not meaningfully move the business forward.

So what does?

I have a thriving business because I have an invisible army—a nurtured group of 200+ former clients, peers, and advocates who know exactly what to say about me when my name comes up—and how to bring my name up when they hear specific triggers.

I do not leave this to chance.

I have made a habit of checking in regularly to provide insight on the market, add value, and yes, assess how others are talking about me—and updating how I’d like to be spoken about to the market if something is off.

When a potential client asks around about me, they don’t hear “Jacob is a good career coach.”

If they do, it’s still appreciated—but it’s weak and it creates noise I must overcome in the sales process. Leads from that messaging are much harder to close—almost not worth it.

What they actually hear:

“Jacob sees the blind spots in your positioning and shows you how to negotiate for what you’ve been leaving on the table—without adding risk.”

Or simpler: “He’s your secret weapon when compensation is on the line. You want him in your corner.”

Notice the precision?

It defines the Problem (you’re undervalued).

It defines the Outcome (you want more money).

It defines the Risk Mitigation (you don’t want to blow up the offer).

That isn’t luck. That is architecture.

Architecture that I learned from their feedback in the first place.

I didn’t just hope they would say that. I asked about their experience, learned, adapted, and then trained them to say that. And because they all use the same specific language, the market accepts it as objective truth.

In return, I craft their narrative with them, make introductions with that narrative, and adapt as we learn.

And round and round we go.

The process I’m about to show you isn’t complex. But it requires precision. And it starts with understanding that your reputation isn’t built by what you say about yourself—it’s built by what you train others to say when you’re not in the room.

Here is how you build your own invisible army.

Weaponizing “The Illusory Truth Effect”

Your brain is lazy.

Not in a bad way—it’s just efficient. It takes shortcuts to save energy. And one of the most powerful shortcuts is this—if you hear something multiple times, your brain starts treating it as true—especially from a person of authority that you respect.

This is called the Illusory Truth Effect.

Psychologists Hasher, Goldstein, and Toppino discovered it in 1977. They found that repetition alone—without any additional evidence—creates the feeling of truth. Your brain uses Fluent Processing as a proxy for accuracy.

Translation: “If this information comes easily to me, it must be reliable.”

Here’s why this matters for your career:

If three unconnected people tell a recruiter, “Sarah turns chaotic growth into scalable infrastructure,” the recruiter’s prefrontal cortex doesn’t just remember you. It accepts it as an objective fact to save cognitive energy.

The recruiter isn’t being lazy or stupid.

Their brain is doing what brains do—looking for patterns to reduce cognitive load. When the same specific language appears three times from different sources, the brain stops questioning and starts believing.

Here’s what this looks like in practice:

Scenario A (Improvisation): A hiring committee hears three different stories about you. One person says you’re “strategic.” Another says you’re “a great culture fit.” A third says you “work hard.”

The result?

The committee’s brain has to work to synthesize this. That triggers cognitive load. In a high-stakes hiring decision, confusion creates uncertainty. And uncertainty equals risk.

Scenario B (Orchestration): That same committee hears the exact same phrase from three unconnected people: “Sarah turns chaotic growth into scalable infrastructure.”

The result?

The brain shortcuts the evaluation. It assumes, “If everyone is saying it, it must be an objective fact.”

This isn’t manipulation—it’s precision. You’re giving people the language to describe what they’ve already seen you do.

This is the asset you’re building. Not awareness. Not visibility.

Cognitive Ease.

When a hiring committee hears consistent, specific language about you—from multiple sources—they don’t experience it as “sales.” They experience it as consensus reality.

Daniel Kahneman calls this Cognitive Ease in his work on decision-making. The easier information is to process, the more true it feels.

Consistency across sources = easy to process = trusted.

Now here’s the part most people miss:

Generic praise creates Cognitive Friction. Specific language creates Cognitive Ease.

When someone says “They’re a great leader,” the hiring committee’s brain has to work.

Great how? Compared to who? In what context?

But when someone says “They turn the chaotic growth you’re experiencing into scalable infrastructure,” the brain relaxes.

That’s specific. That’s a real thing. I can picture that.

Robert Cialdini calls this Social Proof—we don’t evaluate people in isolation.

We use what others say as a cognitive shortcut.

The trap is that most people are terrible at advocating for you because they improvise. And because you left it up to chance.

Your job is to orchestrate all of this.

Your reputation is either compounding interest (coordinated, repeated messaging that builds value over time) or depreciating liability (random, improvised praise that sounds like everyone else and erodes your differentiation).

Leaving it to chance creates noise. Coordinating it creates revenue.

For example, I work with multiple leaders who have 100,000–250,000+ followers on LinkedIn.

Several of them make under $100k annually. They’re broadcasting to an audience, but no one is coordinating their message in the rooms where decisions happen.

And as a result—their scale doesn’t translate to revenue.

I also work with executives who have under 500 connections. Several of them command $2M+ compensation packages.

The difference?

The influencer is broadcasting. The executive is coordinating.

So why are we so quick to tell our colleagues—”You have to be more active on LinkedIn!”

Followers = Attention.

Invisible Army = Revenue.

The leaders who understand this don’t leave their reputation to improvisation. They manufacture Cognitive Ease by ensuring that when their name comes up, the same specific language appears—over and over—until it becomes indistinguishable from truth.

You’re not manipulating anyone.

You’re just understanding how brains work—and giving them what they need to trust you.

So let’s talk about what you give them.

Read more

Most executives operate under the false assumption that there are only three ways to build a high-leverage network.

Option A: You cosplay as a “LinkedIn Influencer,” posting platitudes about leadership at 8:00 AM everyday, hoping the algorithm blesses you with inbound leads.

Option B: You send vapid, “let’s connect” spam messages that are rightfully ignored by anyone with real authority. Seriously, I have over 400 of these right now—why are you wasting your time?

Option C: You go to in-person mixers, wearing a sticky note name badge, practicing your elevator pitch while eating bad cheese and praying no one talks to you.

Let’s call this what it is: Chewing glass.

It is painful, it is inefficient, and worst of all, it signals low status—because let’s be honest—the top senior leaders don’t have to do this.

People chase them.

If you are chasing people, you are—by definition—below them in the power dynamic. The market can smell the desperation of “Just checking in!” email from a mile away.

But there is a fourth way.

It is a silent, surgical approach used by the best sales professionals in the world (credit to Jordan Crawford on this one).

It is called the Permissionless Value Proposition.

Or as I like to call it, giving more than you expect to get in return—without asking whether you should.

Just do it.

Instead of asking for a meeting, you deliver a custom “micro-gift” of insight so specific and valuable that they would pay to receive it.

This is how you build a reputation as the executive who always delivers value, without ever posting a single “thoughts on leadership” thread.

Because, if you’re actually leading in a senior leadership position—ain’t nobody got time for that!

The Biology of the “Cold” Outreach

To understand why traditional networking fails, we have to look at the hardware—your brain.

The human brain is a prediction machine designed to keep you alive. When a stranger approaches you—whether in a dark alley or a LinkedIn DM—your Amygdala (the threat detection center) immediately tags the interaction as a risk.

• Do I know this person? No.

• Do they want something from me? Yes.

• Verdict: Threat (or Nuisance). Delete.

When you send a cold connection request, you are literally triggering a biological defense mechanism in your target.

You are fighting millions of years of evolution that screams, “Stranger = Danger.”

If you’re dialing for dollars—God bless you, but please recognize how you—and 10 to 15 others that look like you everyday—make our lives worse when you call us and follow up with an endless email drip.

You cannot win this fight with a “better subject line.” You have to bypass the Amygdala entirely.

To do that, we are going to leverage two psychological principles:

1. The Mere Exposure Effect: The more we see a face, the more we trust it (provided the context is neutral or positive).

2. Pavlovian Conditioning: We are going to train your target’s brain to associate your headshot with a dopamine hit of high-value insight.

We aren’t going to “network.” We are going to engineer familiarity.

Here is the protocol.

Read more

But silence has a dark side.

If you strip away the noise, the titles, and the frantic motion... what is left?

For many executives, the answer is terrifying: Nothing.

I especially felt this way as the CEO of Discover Podium. Every personal relationship suffered while I gave everything to leading the company for 5 years.

We have built a generation of leaders who are professionally successful and socially bankrupt.

We call it “lonely at the top,” as if it’s a noble sacrifice—especially in America.

It isn’t. It is a structural failure.

Isolation is not just an emotional state; it is a biological malfunction.

When a primate is isolated from the troop, cortisol spikes because they are vulnerable to predators. In the boardroom, this manifests as hyper-vigilance, paranoia, and the inability to trust your own judgment.

Maybe this is why hostile private equity takeovers and RIFs that impact tens of thousands can be just another Tuesday afternoon to an executive tasked with making the numbers work for shareholders.

You cannot lead effectively when your nervous system is convinced it is under siege.

To fix this, I’ve brought in Chelsea and Jack, co-founders of Becoming the Bridge.

They don’t just teach community; they teach biological reconstruction.

Here is how to rebuild the tribe you sacrificed to get to the corner office.

“My entire identity is tied up in my career… and it doesn’t feel good anymore.”

This wasn’t the first executive we’d heard this from. A classic example of “what got you where you are won’t get you where you’re going.” And it won’t feel good if you try to force it either.

How do you get unstuck?

Intentionally surrounding yourself with a community of people who will shake you from patterns and call out the best in you. Support you through peaks and valleys. And make it easy for you to remember who you are.

But that doesn’t come naturally in our corporate careers.

The Biology of Co-Regulation

Neuroscience introduces us to the concept of Co-Regulation.

Humans are open-loop biological systems. We cannot regulate our nervous systems entirely on our own; we need others to stabilize us.

A dysregulated nervous system (high stress, fight-or-flight) cannot calm itself down solely through willpower or meditation apps. It requires the presence of a regulated nervous system to mirror safety.

This is why the “Lone Wolf” leader is a biological myth.

You literally cannot access your highest cognitive functions—like complex strategy and moral reasoning—without a tribe to anchor your biology.

Without that anchor, you aren’t just lonely. You are cognitively impaired.

What begins as ambition becomes entanglement.

What starts as drive can morph into self-definition.

And without realizing it, the ladder you’ve climbed has narrowed your world.

The Cost of a Career-Rooted Identity

When our identities become fused with our achievements, several things begin to happen that we don’t always notice in the moment:

Our social circles shrink.

People know our title before they know our heart.

Imagine a senior leader who realizes that most conversations begin with “How’s Q3 looking?” rather than “How are you holding up?”

Their connections become narrower and more transactional, even as their visibility rises.

We stop being witnessed as humans.

Conversations become transactional—metrics, goals, restructures, performance. When you try to mention a personal challenge, the discussion snaps back to KPIs.

Not out of malice—just out of our cultural momentum.

Over time, we stop bringing our humanity into rooms where it never seems to fit.

We lose access to diverse reflection.

We’re surrounded by people who reinforce who we’ve been, not who we’re becoming.

When we crave more purpose—we often keep getting the same advice—accelerate, scale, push—because our circle reflects the identity they’ve historically performed, not the one we want to grow into.

Our emotional range compresses.

The stakes feel higher, the pressure intensifies, and vulnerability gets quieter.

We will default to “I’m good” even when we’re depleted. We believe steadiness is required at all times, and slowly our emotional landscape narrows to “fine” and “under control.”

Our sense of fulfillment dulls.

Even massive success feels strangely muted when there’s no one who really sees you.

A career-defining win lands with a thud because the people celebrating see the outcome, not the human experience behind it.

White-knuckling it alone isn’t just unsustainable—it’s detrimental. Mentally, emotionally, even physically.

And it’s easy to distract ourselves.

There is always another board deck, another flight, another fireside chat, another spreadsheet calling for updates. But there is a cost when we make more time for our dashboards than our inner landscapes.

If you’re not giving your soul as much attention as your spreadsheets, eventually something starts to ache.

Because work—no matter how impressive—is not meant to replace your humanity.

Two Strangers Asking the Same Question

Hi—we’re Chelsea and Jack.

Long before we knew each other, we were living parallel lives—VP titles, President’s Club, hypergrowth metrics, and a quiet desperation we medicated with alcohol and motion.

Jack found his turning point in rehab and then a retreat in Costa Rica. Chelsea found hers when the pandemic stripped away the stage and she took a leap of faith with a retreat of her own.

Both of us stopped performing and started asking:

Who am I without the armor?

Maybe you have felt this way too.

We both sought something deeper.

Steps to Reconnect With Your Whole Self

You don’t need a sabbatical or a spiritual pilgrimage to change your experience of leadership.

You need intention—and a few practical steps.

1. The Relationship P&L (Social Audit)

Most executives treat their energy like an unlimited resource. It isn’t. You need to audit your relationships with the same rigor you audit your financials.

Open your calendar. Look at the last 10 people you met with outside of immediate direct reports.

• Who is an Asset? Who leaves you feeling clearer, sharper, and more regulated?

• Who is a Liability? Who leaves you drained, defensive, or needing a drink?

Stop treating energy vampires like necessary expenses.

They are bad debt. Write them off.

You need to ruthlessly curate the people who have access to your nervous system. If they reinforce your armor, they go. If they speak to your humanity, they stay.

2. The ROI of Time (Energy Audit)

Your calendar is a mirror. It reflects what you truly prioritize, not what you say you value.

• Where are you getting a return? Identify the moments where time moves quickly because you are in your “Zone of Genius.”

• Where are you bleeding? Identify the moments where you are performing a version of leadership that no longer fits.

Many leaders realize the work they are “known for” is the work that is killing them.

This audit isn’t about time management; it’s about energy management. If you are operating from an empty tank, your strategy is worthless.

3. Make Time for Your Soul

Leadership is not just about strategy. It is about alignment.

Even the most precise Social and Energy Audits will fall flat if there is no space where you can meet yourself honestly.

This does not require a monastery.

It can look like ten minutes without your phone, a weekly walk without headphones, a monthly hour with someone who knows you beyond your title.

The question underneath all of this is simple:

Do I like who I am becoming in the way I am currently leading?

If the answer is “not quite,” you are not broken. You are simply ready for a different way.

Social Audits, Energy Audits, and Soul Time are basic practices, but for most executives, they are radical. They create the conditions for you to lead not only more effectively, but in a way that actually feels good to live inside of.

How This Might Look Moving Forward

We see time and time again when leaders reconnect to your inherent worthiness, rediscover their vision, and expand into new possibilities—through community, coaching, and the transformative power of being deeply seen—all of the best things in your life become available.

We’ve experienced firsthand how isolating leadership can be—and how profoundly life-changing it is when you’re no longer carrying it alone.

You can grind your way to the top, but you cannot grind your way to fulfillment.

Your career can be extraordinary. Your leadership can be impactful. But you cannot do it alone.

Stop trying to be the hero. Start building the tribe.

Jacob’s Take

There is a pervasive lie in executive culture that says dependency is weakness.

We convince ourselves that if we just work harder, optimize more, and sleep less, we can outrun our biology.

We treat “community” as a soft “nice-to-have” that we will get around to once we exit or retire.

Or it’s just a gimmicky collection of semi-lookalikes networking to find a job.

As I wrote last week, the market pays for your clarity, not your stamina.

And as Chelsea and Jack just proved, you cannot have clarity if your nervous system is constantly scanning for threats because you are isolated.

If you are looking for a tactical reason to care about this, here it is: Isolation is expensive.

It costs you your judgment. It costs you your resilience. And eventually, it costs you the very career you are sacrificing everything to build.

You would never run a company without a Board of Directors to check your blind spots. Why are you trying to run your life without one?

Stop giving your most limited resource—your energy—to people who treat it like a free commodity. Be as rigorous with who you let into your life as you are with who you let onto your cap table.

Winning alone isn’t winning.

Go find your tribe.

Connect with Chelsea and Jack on LinkedIn to learn more about their executive cohorts at Becoming the Bridge.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.