Let's be blunt. It feels good to be wanted.
To be desired. To be pursued. To feel valued.
Let's say an attractive person takes an interest in you—with a flirty smirk, a kind gesture, or a sweet gift.
The attention is flattering. That lingering glance across the room ignites something within you.
The attention feels good. You haven't been checked out like this in years. You still got it, baby.
It feels good to be adored.
But what if that adoration comes from someone you're not interested in? Or by someone you find annoying or incompatible?
Now consider this.
What if someone offered you a 30% raise to ignore that pit in your stomach telling you something's wrong?
This is precisely what happens in our professional lives when we passively react to opportunities that others dangle before us.
Like following a stranger's GPS without knowing the destination, we surrender our direction to recruiters, bosses, and market trends that offer everything except alignment with our core values.
Welcome to mediocrity in corporate America.
Welcome to your career.
The Path of Deliberate Resistance
Hikers heading toward a summit naturally take the path of least resistance when not paying attention.
They will often zig and zag to avoid strenuous obstacles such as hills, rough terrain, or a pit of rattlesnakes if they're from my neck of the woods.
We naturally tend to follow the easiest route, which doesn't just apply to hiking trails. It manifests throughout our careers with far more significant consequences. The professional "snakes" you encounter aren't just momentary hazards—but transformative threats.
Their venom will shave a decade or two of your life, and their gaslighting will have you questioning why you're even trusted to breathe without their all-knowing approval.
With AI now managing job matching and career planning, it's easy to believe someone else can chart your perfect career path. Algorithms now promise to identify your talent, match you with opportunities, and map your climb to the professional summit—all without you needing to think critically about direction.
You no longer need to blaze your own trail.
Instead, you can now rely on sharing a handful of buzzy descriptors, work for an established company, and wait for opportunities to find you.
But letting computers decide your future is not just risky—it's a surrender of your agency. I call this algorithmic complacency.
If you're not intentional, you'll box your world into a carefully curated algorithm, limiting your potential and crushing your dreams.
Systems today are designed to create more of the same or similar experiences. Over and over and over.
"We" know what it takes to get you to click.
Welcome to your career roadblock—outliers need not apply.
Jacob's Orwellian Fairytale
Once upon a time, there lived a nothing person aptly named Persnickety Milquetoast.
They were your typical tall, short, darkish, light-haired, heavy-set, thin human.
You know the type.
Persnickety played by the rules and checked all the boxes—as any good, law-abiding citizen often does.
They blitzed into college with wide-open eyes and inspiration. They wanted to help others and change the world, rescue dogs, or open a health club.
The real world had other plans.
Society didn't just suggest—it demanded. It wagged their haggard fingers and asked Persnickety to obey. To comply and pay their dues. To take a less direct, zig-zagged path to the summit—just like our metaphorical hiker, but with more crushing of the soul.
Persnickety begrudgingly obliged and even made good money as an intern at the same soulless software company that made the computer they used to cheat on their SATs.
No big deal, Persnickety thought.
After all, the MBA and the soulless job would only be temporary. It would eventually build enough savings to fund their real dreams. Their authentic life. Someday.
Milquetoast saved money and did well. All to plan.
Then anguish disguised as serendipity came knocking—wearing the same face as your last recruiter call.
"Hello, Milquetoast. Do I have an opportunity for you? Just do what you're doing now… but with more pressure and a team! And you'll need to work twice the hours—but you'll also get 30% more pay! How good is that?! We need you. You're the best. WE ADORE YOU."
It feels so good to be wanted.
"More is more—and that is good. I accept," snorted Persnickety, only semi-defeated but fully sedated by the promise of future freedom.
Serendipity came knocking 3-5 more times over the years. And with each new opportunity, Persnickety's authentic dreams didn't just punt down the road—they were systematically exterminated from memory.
Fast forward.
Persnickety lives in a termite-colony condo just outside every imagined metropolitan cityscape. They live in the highest tower decked out with Ikea and a smart fridge that shows their social media feeds. Hell, Persnickety may even be a model for the cover of the next issue of Fortune magazine.
They found a partner, had a few kids, and paid the way for a good family life. They even go to Hawaii once a year! One could hardly complain about these first-world problems.
Persnickety now has an epiphany while sitting on a mountain of valueless money in their dwindling years.
Their life was both everything and absolutely nothing.
No dogs were rescued. No health clubs were built. No dreams were obtained. Their family hardly recognizes them, and their doctor is disappointed in how they handle stress.
And so we have a fairytale that leads everywhere but happily ever after—a cautionary tale of surrendering to the algorithmic path of career mediocrity you're reading right now.
Take A Stand: The Discipline of Intentional Refusal
If there's a thread of common advice I've received from clients, it's that nobody looks back from their deathbed wishing they had worked more. Especially working more for uninspired organizations that don't align with their dreams.
What's fascinating is that I rarely find greed to be the primary trap for executives caught in their personal dystopia.
Instead of greed, what traps most executives is a complex interplay of social expectations, personal identity, and decision patterns.
Many make career sacrifices, believing they're doing what's necessary for their families and loved ones. They take the promotions, relocations, and increased responsibilities because success without visible struggle doesn't feel like they're doing enough.
These sacrifices often stem from genuine care—providing better opportunities for their children, supporting aging parents, or ensuring financial security for those who depend on them. The executive path becomes a testament to their commitment and work ethic.
Yet paradoxically, the more challenging but more rewarding path sometimes appears selfish on the surface.
Choosing alignment over advancement, purpose over promotion, or boundaries over burnout can seem indulgent when compared to the socially celebrated route of constant sacrifice.
Executives often miss that modeling authentic success—showing their children and peers what purposeful work and balanced achievement look like—may be the greater gift than another zero on the bank statement or a more impressive title.
The courage to resist appealing but misaligned opportunities isn't selfishness—it's the ultimate act of leadership.
It shows others what's possible when you direct your career with intention rather than letting external forces direct it for you.
Yet this courage remains rare, even at the highest levels of business.
Ironically, this creates a peculiar contradiction at the core of corporate leadership.
These "leaders" become walking paradoxes—commanding vast resources and making decisions that affect thousands, yet strangely powerless when steering their own professional journeys.
Like Milquetoast, they drift where the stiff wind blows them, following paths of advancement that may lead to positions of authority but not necessarily to places of purpose or fulfillment.
Their impressive external power masks an internal surrender of direction—a capitulation that undermines their capacity for authentic leadership, regardless of what their business cards might proclaim and what their company credos publicly espouse.
The most essential professional skill you're not developing is the discipline of strategic refusal.
Just because you can, and you're capable of doing something in your career—doesn't mean you should.
Remember—you will either suffer the pain of discipline or the pain of regret. One is temporary. The other permanent.
The moral is—when you wait for opportunities to come your way, you often get more of the same. Some jargon-centric marketers may call this inbound.
I call it professional surrender.
The system is designed to trap you in the comfort zone you either fell into or chose to create for yourself. Every algorithm-driven suggestion, every recruiter call, and every "perfect opportunity" reinforces the walls of this bubble.
The happiest executives I know take a stand, create the conditions for their success, and face their discomfort head-on. They understand that true career freedom comes not from saying yes to better opportunities but from saying no to the wrong ones.
But rejection alone isn't enough—you need direction.
Once you've mastered saying no, the next challenge is rediscovering what you should say yes to.
Rediscovering Your True North
Let me share something transformative I've witnessed with hundreds of leaders who broke free from their algorithmic prisons. This isn't about more tasks on your already overflowing plate—it's about rediscovering the compass you've always possessed.
The Excavation of Authenticity
Imagine uncovering a map that's been buried beneath years of "should," "must," and "more."
This excavation happens in three natural layers:
First, acknowledge the landscape you've built.
Without judgment or criticism, observe the territory of your achievements. The exercise isn't about measuring success—it's about witnessing your journey with fresh eyes. The simple act of seeing your path objectively often reveals patterns invisible during the climb.
Try this: Get a big piece of paper and some colored markers. Get physical, not digital. Draw a line across the page — that's your career so far. Mark your jobs, big projects, and important moments along this line.
Don't worry about whether something was "good" or "bad" — just put everything down.
This hands-on mapping helps you see patterns you might have missed while otherwise busy trying to get through each day.
Then, follow the energy.
When you look at your proudest moments, what specifically brought you joy?
Was it the creative breakthrough, the strategic insight, the human connection, or the measurable impact? Your energy is more revealing than any performance review. The moments that energized you weren't accidents—they were glimpses of alignment.
For example: An executive realized he lit up when mentoring others, not during his "actual job" duties. His energy spiked when developing talent, not when climbing the corporate ladder. Acting on this insight, he left his prestigious role for a smaller company. He now thrives as a player-coach who builds future leaders rather than navigating toxic politics in a rigid system.
He still gets paid well, too.
Finally, reconnect with your vision.
What did you naturally gravitate toward before the world told you what success should look like? What problems did you solve before anyone asked you to? Those weren't just youthful fantasies—they were your authentic expression before external validation became your compass.
For example: Think about what genuinely excited you before career expectations took over.
In my case, I was passionate about filming, photography, and editing—creating visual stories that captured people's attention.
Yet somehow, I found myself in Silicon Valley marketing roles, crafting strategies for products that left me feeling empty inside.
Maslow would have spotted my predicament instantly—I was trading my passion and purpose for a paycheck that covered my expensive San Francisco apartment.
Maybe you feel this way, too.
While people praised my rapid career advancement, I felt like an impostor when they sought my advice because I wasn't happy.
My breakthrough came when I realized what truly energized me—I couldn't see a meaningful impact from the tech I marketed, but I witnessed immediate transformation when helping someone navigate their career.
My "aha" moment was recognizing I could apply my expertise to people's careers instead of products. Seeing the real impact on lives brings me joy.
It makes work feel like play—and taking risks feels necessary because it's bigger than me.
This clarity now drives every professional decision I make. I build frameworks that help leaders find meaningful work aligned with their values. I guide them through career transformations that increase both their compensation and fulfillment.
While the work presents challenges—scaling this impact fuels me in ways my corporate career never could.
Your Personal North Star Filter
When new opportunities arrive (and they will), you must pass them through a simple but profound filter.
- Does this opportunity energize rather than deplete you?
- Does it honor your deepest values rather than just your market value?
- Does it move you toward meaningful mastery rather than just measurable advancement?
- Will it create a legacy you'll proudly claim in your final chapter?
This exercise isn't about perfect choices—it's about authentic ones.
The most aligned path isn't always the most comfortable one initially. The challenges of growing feel different from the drain of being in the wrong place.
If an opportunity fails two or more criteria, you know your answer. (Plus, you have incredible leverage to practice your negotiation skills.)
The most profound shift happens when you stop seeing your career as something that happens to you and recognize it as something flowing from you.
This isn't another methodology to implement—it's remembering who you are and what truly matters.
Your moment of awakening isn't when you discover something new—it's when you recognize what you've always known but forgotten along the way.
Stay fearless, friends.
