Why Doing It All Yourself Is Killing Your Career

The hidden support systems top leaders use to preserve their best thinking—but most are too afraid to build.

While you grind yourself into dust to prove you can “do it all,” the most successful—and sustainable leadership careers—build invisible support systems that make their performance look effortless.

You and I both know that it’s anything but effortless.

Executive presence doesn’t require superhuman capability—but it sure looks like it sometimes.

Rather, it demands smart resource allocation that many leaders don’t admit they use or are too hesitant to invest in properly.

The science backs this up in telling detail.

Leaders make thousands of decisions daily—research suggests at least 122 informed decisions, plus hundreds more micro-choices you don’t even register.

Your brain depletes cognitive resources exactly like muscles exhaust after heavy lifting.

Stanford research proves this isn’t just “feeling tired”—it’s measurable cognitive degradation that destroys your judgment quality.

Yet we glorify the myth of the self-sufficient leader who never needs help.

Look at the contrast.

Struggling leaders wear burnout as a badge of honor and refuse to outsource anything.

Meanwhile, winning leaders delegate everything from inbox management to keynote design, personal training, stylists, headshot photographers, content strategists, and publicists.

The difference isn’t typically raw capability or work ethic or simply access to the funds once you reach impactful seniority. Rather, it’s more often your willingness to invest in the infrastructure that preserves your decision-making capacity for what matters most—including your family.

Here’s where you should pay attention.

Your toughest competitors don’t try to do more themselves. They build support behind the scenes that you don’t always see.

We’ve learned of some roles where all three finalists for a coveted senior leadership position at a unicorn company each invested over $50,000 personally in coaching—and that’s not considering the other support they invested in.

One of the candidates that got passed on considered a near 6 figure investment in an Ivy league accelerator program to correct their near miss.

After all, for them, every month they are unemployed, they’re losing over $200,000 in opportunity cost.

Holy smokes!

That’s the market we all navigate right now.

I’m not sharing this to make you feel inadequate if you can’t write those checks today.

I’m showing you what you’re actually up against so you can make informed decisions about your career trajectory.

Some of your competition operates with resources and infrastructure you don’t see.

Understanding this reality doesn’t mean you’ve lost—it means you can stop blaming yourself for feeling overwhelmed and start building the support you can afford right now, even if it’s just one hire that buys back five hours a week.

Every hour you spend proving you can handle administrative tasks is an hour they spend thinking three moves ahead.

Or an hour that they get 3-5x the impact from because someone is folding laundry, managing finances, running to the dry cleaners, and preparing their keynote all at the same time.

While you’re exhausted from scheduling conflicts and handling the kids’ laundry—they show up to meetings with full cognitive capacity.

The gap widens and compounds daily—and most leaders don’t even realize they’re running a race they’ve already lost. Yet here we are, continuing to push a large boulder up an increasingly steep hill.

Maybe it’s time for a fresh perspective.

I Had to Unlearn Everything About Money and Help

I learned about money and support systems the hard way.

I survived homelessness in my twenties, slept in skateparks and on disc golf courses, and operated in pure survival mode for years. I developed what psychologists call a “scarcity mindset.”

I had a toxic relationship with money that nearly destroyed my ability to build the career I have today.

I despised wealth.

Not the people who had it necessarily, but the concept itself. Especially because I didn’t grow up around it, my friends didn’t have it, and it didn’t appear there was a path to obtain it. I simply didn’t understand money at all.

So naturally, I villainized it.

And when you hold contempt for something, you sabotage your ability to negotiate for it—whether you deserve it or not. You shut it out of your world.

I climbed fast anyway.

At 19, I edited episodes of The Deadliest Catch (that won an Emmy) after a chance encounter in a Staples store with the producer. (That was unpaid work by the way, but it sure sounds cool.)

I bounced through short marketing stints and failed mostly upwards, except for a 6-month stretch of homelessness. By 24, I directed marketing at a Fortune 500 company. By 26, I held my first VP of Marketing role.

All without a college degree, because in 2008, the ROI didn’t pencil out when gas hit $5.50 a gallon and entry-level jobs paid $8 an hour.

Here’s what nobody tells you about that kind of rapid ascent—I built it by grinding myself into this self-loathing capitalist sacrifice and told myself it was for some sort of greater good.

In reality, I was just faking it until I was making it—or something poetic like that. Maybe you can relate to this while you were, “paying your dues.”

Eighty-hour weeks, sometimes pushing past 100 as CEO of Discover Podium a few years later. I proved “I can do it all myself” like it measured some kind of virtue.

I wore burnout as a badge of honor because if you didn’t feel exhausted, you weren’t working hard enough. (Thanks Dad.)

Asking for help felt like admitting I ran a fraud. My scarcity mindset actively blocked any thought of delegation.

Then something shifted, really in the last 24 months or so.

I started making real money—sometimes $10,000 for a single hour of counter-negotiation work with executives if our win was big time. My average hourly rate hit $2,500. And suddenly, the math became impossible to ignore.

If I billed an hour at $2,500, why did I spend that same hour doing laundry I could outsource for $50?

Am I scared of being perceived as an oligarch for passing that money through to someone else running their business? Something as simple as cleaning and folding laundry?

I’m not too good for cleaning my own underwear—am I?

Even if I made $200 an hour, shouldn’t I hire someone to handle my laundry for an hour, sell one more hour of consulting, then spend 2 hours with my family for dinner?

That’s putting your money to meaningful work.

The resistance wasn’t logical—it was psychological.

Years of scarcity thinking made delegation feel like weakness. Like self-indulgence. Like I was becoming one of those people I used to resent.

But here’s what changed everything—I realized money isn’t the end goal.

It’s a pass-through.

It flows through me to areas where I see fit. When you have more, you can be more generous. You can reward great work. You can bring the right people into your orbit. You can smooth so much friction in your life if you let it.

Or you can hoard it all in a pile and never use it for some reason.

The breakthrough came when I stopped asking “Can I afford this support?” and started asking “Can I afford NOT to have it?”

Any support that gives me five more hours weekly with my sons Noah and Nathan and my wife Mary isn’t a luxury. It’s absolutely non-negotiable.

After all, a few extra hours with my family is a lot cheaper than a divorce. And let’s be honest, time with my kids is a lot more fun than writing articles every week, no offense y’all.

A professional photographer who captures the work I’m doing so I can focus on doing the work rather than documenting it?

That’s not vanity—it allocates resources more effectively and allows me to grow my family more meaningfully.

Many leaders I work with carry the same toxic relationship with support that I had—and some of it is baked into childhood trauma that we can’t seem to shake.

They invest millions in business infrastructure but refuse to invest in their own operational effectiveness (unless their company sponsors it). They burn cognitive resources on administrative decisions while claiming they “can’t justify” the cost of help.

Yes, the Cobbler’s children have no shoes. I’m guilty of this.

The leaders we often admire most?

They figured this out years ago.

They built comprehensive support ecosystems while we were still trying to prove we could handle everything ourselves.

The pattern I observe while working with senior executives is unmistakable—the people who resist building support systems the most plateau first.

They confuse self-sufficiency with leadership effectiveness.

Research backs up what I see—decision fatigue shows that depleted leaders make measurably worse decisions. Meanwhile, Gallup research demonstrates that CEOs who excel at delegation generate 33% more revenue than those who don’t.

Your competitors reading this don’t think “I should try doing more myself.”

They think “I need to build this infrastructure faster.”