The Conformity Trap

If you're anything like my coaching clients—founders, PMs, authors, clinicians, business owners, you probably have felt that burning drive to make an impact by following your internal compass. 

In his book Mastery, Robert Greene calls this drive our "primal uniqueness", a voice or force that acts like a seed planted at our birth.

It wants to grow, transform itself, and flower to its full potential...The stronger you feel and maintain it as a force, a voice, or in whatever form, the greater your chance for fulfilling this life's task and achieving mastery.

But this force can be weakened or cast into doubt by an adversary: the social pressure to conform.

Of course some amount of conformity is necessary. We are social creatures after all. And especially earlier on in our professional lives, we have to learn the rules of the game, the unspoken dynamics that govern our field.

Greene describes this work as like being an anthropologist studying a foreign culture:

You can observe such rules by looking at those who sit or are on their way up in the hierarchy, who have the golden touch. More tellingly, you can observe those who are more awkward, who have been chastised for particular mistakes or even been fired. Such examples serve as negative tripwires. Do things this way and you will suffer.

But the danger is what happens when you get too focused on the rules, too good at conforming. This often is what happens when someone gets good at political maneuvering without a connection to their own mission.

So over time, we learn to adapt—to work inside the system. All of us have learned some skills of political maneuvering: supporting the dubious idea of a friend , dropping a disagreement you see you will lose, praising a senior leader's ego, or strategically withholding your true perspective. 

But outliers often struggle here. For some of us, that internal voice is so strong, it's hard to keep it from breaking through when we see something we find compelling—or distasteful.

This is the tradeoff. Shreyas Doshi, an ex-PM leader at Stripe, Google, and Twitter puts it in these terms:

"Being highly competent but politically unsavvy relative to your peers—whether you’re at a fast‑growing startup or a big company—might prevent you from reaching your full potential in conventional terms (org size, title, etc.). Yet it keeps you closely connected to who you truly are."

This was me in most of my jobs. I often felt inspired by the mission and connected with the people, but I didn't always agree with the strategy or how I was asked to do the job. When leadership said "this is the plan", I would say "but what about that other path?" When they said "jump," I didn't immediately ask "how high." 

At Meta I once was asked to lead a cross-org initiative drive better internal engineering documentation so teams could build faster with unfamiliar code bases. Our research found that engineers didn't feel recognized in performance reviews for creating or maintaining docs, so they didn't do it. The senior eng manager on the project believed there was a technical product or feature that could drive this behavior but I stubbornly fought for a cultural change (i.e. change how engineers are evaluated). We butted heads often and in the end, hiring freezes and reorganization made the entire project moot. 

I think if I had more politically savvy I could have engaged with him differently, brought more people to the table, and even if we shipped something less fundamentally effective, I might have gotten the promotion this project was meant to secure. 

Given that bitter end result, I’m heartened by Doshi’s views:

Over time, this builds a quiet, intrinsic confidence that many of your peers will lack despite their big titles and large orgs.

What you do with that confidence is up to you, but in many cases it allows you to make more authentic career choices your former peers say they would love to make “if only the timing were right.”

Of course, what appears to be a timing problem is really a confidence problem — the quiet, authentic kind of confidence.

I know many of the people I worked with at Facebook / Meta were glad to be there, enjoyed the work, or at least found it largely aligned with their professional and personal goals.

But I also know that plenty of them wanted to start their own companies, travel more, or explore other career paths like coaching or building their own products—yet found themselves unable to make the leap.

Often these were really successful PMs and managers—at least on paper. They got promotions, they were put on the most visible projects, and they had the respect of their teams and superiors.

But on some level, they were also afraid to bet on themselves. The very political savviness that had served them so well now became their prison—they had too much invested in the system to risk walking away from it.

On their own messy, inconvenient desires. To step away from the warm glow of corporate recognition—that steady dopamine hit of performance reviews and team happy hours and kudos on team chat that made them feel safe, valued, approved.

But here's the thing—you stay in water long enough, and you forget it's even there. Every system is only one of many ways of being. Here's Doshi again.

"Every parent with more than one child and everyone with siblings knows this truth: people are different. No amount of forcing, lecturing, modeling, or incentivizing will change that. Yet our societal conditioning runs so deep that we come to believe everyone else should not only resemble us but should also adopt our beliefs, our priorities, and our way of thinking — as if our own ideas were the universal template everyone else must conform to."

From just a few months old, I saw a desire in my daughter to climb and stand. I didn't give that to her through my parenting. She was crawling and pulling herself up to standing by 6 months on her own, while other babies still happily on their bums, content to stay in one place.

Every individual has a unique constellation of traits which makes them more or less suited for certain fields, companies and roles. When those traits distinguish us from our peers, we experience life as outliers.

Humans are remarkably diverse in their interests and abilities, and we're nothing if not incredibly adaptable. Throughout history and across the globe, we've thrived in countless different geographies, embraced vastly different lifestyles, and created rich, varied cultures wherever we've settled.

Breaking from your group's values demands courage. Following our tribe's lead is an evolutionary instinct that kept us alive and helped us, as the social and collaborative species we are, dominate the planet.

But the internet and now AI have lowered the barrier to reaching markets, audiences, and resources in ways that were unimaginable even ten years ago. A single person with a laptop can now reach millions of people through words, software, or media.

This shift has fundamentally changed the risk-reward calculus of following your own path versus climbing someone else's ladder.

The corporate world still offers security and clear progression, but it also comes with golden handcuffs that grow heavier with each promotion. Mass layoffs now abound and even the most loyal workers can find themselves out in the cold. 

Meanwhile, the outliers who embrace their "primal uniqueness" and build something aligned with their internal compass often discover something remarkable: the work doesn't feel like work when it's truly yours.

The question isn't whether you should conform or rebel.

The question is whether you're willing to trust that voice inside you—the one that sees things differently, that questions the status quo, that imagines a better way.

Because in a world where everyone else is trying to fit in, the biggest opportunity belongs to those brave enough to stand out.