By: Me, with a little help from my inner Carrie Bradshaw
I couldn’t help but wonder…
What if the very people we assume to be the most self assured, confident, decisive, unflinching in boardrooms and at TED Talks, are just as riddled with self doubt as the rest of us?
We live in a world where confidence is currency. But what happens when the people holding the most of it, the white, male, upper management archetypes, feel like their wallets are lined with Monopoly money?
Let me set the scene.
He was tall, Ivy League educated, impeccably tailored. His voice was firm, his handshake firmer. But over our third round of Negronis and startup post mortems, he let it slip: “Some days I wake up and think someone’s going to figure out I have no idea what I’m doing.”
I almost choked on my orange peel.
Because in that moment, the man who seemed like the personification of executive level certainty peeled back the Gucci loafer to reveal something so very human. Self doubt. Fear. The secret suspicion that he might not deserve the chair he’s sitting in.
Even white men have imposter syndrome.
Now, I’m not saying we throw them a pity party. Lord knows they’ve RSVP’d to enough celebrations already. But it does raise a curious question:
Is confidence actually about certainty, or is it about performing certainty long enough for it to feel real?
Psychologists say imposter syndrome doesn’t discriminate, though historically, it’s been dressed up as a woman’s affliction, accessorized by workplace inequality and societal expectations. But quietly, behind closed office doors and LinkedIn bravado, many men, especially those in leadership, wrestle with the same gnawing question: Am I really supposed to be here?
What struck me wasn’t just that he felt like a fraud. It was that he hid it so well. Because somewhere along the line, we’ve confused humility with weakness and confidence with omniscience. And no one feels that pressure more than the people who’ve been told since birth that success is their birthright.
But maybe the healthiest leaders aren’t the ones who never question themselves. Maybe they’re the ones who do, but lead anyway.
Studies back this up. According to Harvard Business Review, leaders who display humility, those who admit mistakes, spotlight team contributions, and are open to feedback, are more effective in driving engagement and performance. In fact, research published in the Academy of Management Journal found that humble leaders boost team creativity and collaboration, which are essential in today’s fast paced, knowledge driven industries.
Confidence still matters, of course. But not the kind that silences doubt or drowns out dissent. As Tomas Chamorro Premuzic, a psychologist and leadership expert, writes in HBR, “The most effective leaders are confident enough to be humble.” The sweet spot lies between self assurance and self awareness.
Because here’s the thing: humility isn’t the enemy of leadership. It’s the soul of it. Knowing you don’t have all the answers doesn’t make you unqualified. It makes you curious, open, coachable. Human.
We’re in a new age of leadership, where transparency trumps authority, and empathy edges out ego. Where saying “I don’t know” isn’t an admission of failure; it’s a strategy. The smartest people in the room? Often the ones still asking questions.
So whether you’re a woman climbing the ladder in heels that hurt or a man standing at the top with a suspicious view, maybe confidence isn’t about being certain. Maybe it’s about being comfortable with uncertainty. Maybe it’s not about feeling like you belong but knowing that everyone feels like a visitor at some point.
And if the guy in the corner office still sometimes wonders if he deserves the desk… maybe we’re all doing just fine.
Because imposter syndrome doesn’t mean you’re not good enough.
It means you care enough to want to be better.
And maybe that’s the kind of leader the world needs most.
So the next time you find yourself doubting your seat at the table, remember: even the guys who built the table sometimes worry it’s going to collapse beneath them.
