Why High-Performing Leaders Feel Privately Unsatisfied

BROJO Asia / Pacific

Michael Wells

Most people assume that success and happiness go hand in hand. That once you’ve “made it” — the money, the title, the respect, the freedom — you’re supposed to feel calm, satisfied, and proud of yourself. But if you’re a high achiever, you probably already know that’s not how it actually works.

In this video, I unpack a pattern I’ve seen over and over again since I started coaching high performers back in 2013: the more successful someone becomes by external standards, the more privately dissatisfied they often feel. CEOs, founders, executives, top performers — people everyone else looks up to — quietly struggling with anxiety, emptiness, imposter syndrome, and a constant sense that they’re never quite enough.

I start by sharing the story of one of my clients, Lynn. From the outside, her life looks like a textbook success story. She came from a difficult background, used ambition as fuel, climbed the ladder re...