The Underestimated
Last week, during one of those late night moments when your brain starts connecting dots you didn't know were there, I realized something strange. Every person I genuinely admire has one thing in common: they've all been consistently underestimated. And the more I thought about it, the more I realized this wasn't coincidence.
Raman, who built a company while everyone told her to get a 'real job.' Simar, who got into Stanford after his teachers said he wasn't 'college material.' Me, building my startup at college startup lab while my classmates were chilling at happy hours I couldn't afford. We'd all learned to work in spaces people don't watch.
Because there's something weirdly satisfying about being underestimated, but that's not where it starts. It starts with invisibility. You learn to recognize the look early, that moment when someone's eyes pass right through you, when they've already decided you're not worth the full calculation. The college counselor who suggested community college before looking at my grades. The professor who called on everyone else first. The guy who explained my own project back to me in meetings.
Source: Stockcake
At first, you think it's about you. You must be doing something wrong, saying something wrong, being something wrong. You adjust your posture, your voice, your clothes. You practice being more confident, more articulate, more whatever-they-want-you-to-be. But the look doesn't change.
Then you realize: they're not seeing you at all. They're seeing a category. A checkbox. A set of assumptions they've already made about what someone like you can or cannot do. And that's when being underestimated becomes something else entirely.It becomes a superpower you never asked for. When no one expects you to succeed, failure stops being terrifying. When no one's watching for your next move, you can make moves they never saw coming. When they've already written you off, you're free to rewrite the entire script.
The underestimated learn to work in shadows, in margins, in the spaces between what's expected and what's achievable. We become fluent in a language the overestimated never need to learn: the language of making something from nothing, of finding opportunity in dismissal, of turning invisibility into advantage.
But here's the part that's darker and stranger than the motivational stories want to admit: being chronically underestimated changes something fundamental in your wiring. You stop needing their validation because you've learned to generate your own. You stop waiting for permission because you've discovered that most of what you were taught to ask permission for, you could just... do.
You become dangerous in ways they never anticipated. Not angry dangerous, anger is too obvious, too easy to contain. You become quietly, strategically, unstoppably dangerous. You become someone who builds stuff while they're still debating whether you deserve a seat at the table.The underestimated don't break glass ceilings. We tunnel underneath them and emerge somewhere they weren't watching.
And the satisfaction? It's not revenge. Revenge requires them to know they were wrong. The real satisfaction is simpler and more complete: it's the knowledge that their estimation never mattered in the first place.We work in the space where what's possible has nothing to do with what's expected.
Some people see this and call it resilience. Others call it defiance. But those words still accept the premise that their opinions mattered enough to resist.
The truth is stranger: being chronically underestimated eventually makes you immune to estimation altogether. You stop living in their categories. You stop playing their prediction games. You become ungovernable not because you're rebelling, but because you're operating in a completely different system, one where your worth was never up for debate in the first place.
And once you've evolved past the need for their accuracy, once you've learned to thrive in the space they can't even see, you realize that being underestimated wasn't the obstacle. It was the training.
What I've been Learning:
Going Direct with Lulu Cheng and Jack Altman : Speaking of being underestimated, I've been thinking about this Lulu Cheng and Jack Altman conversation about founder positioning. They said something interesting, when founders are genuinely likeable, people actually want them to win. And there's this sweet spot where you want people to think you're slightly underrated because humans love rooting for the underdog. The key is never seeming overrated. Keep your mission pointing toward something you're still reaching for, not something you've already achieved. Because once people think you've "made it," they stop wanting to help you get there.
Note: Written from my own experience, with Claude helping me structure my rambling thoughts into something readable