The Underdog Syndrome

A while back, I realized there’s this invisible obstacle holding ambitious people back. And I call it the "Underdog Syndrome."

Now, it's not what most people think – it’s not about “imposter syndrome.” It’s about the unique, gritty discomfort of being the ‘least successful person in the room’ and, get this… actually being fine with it.

Let me explain.

We've all been there, right? The worst player on a team, the friend making the least money, or that lone early-stage entrepreneur at a table full of 8-figure founders. It’s uncomfortable, it’s humbling, and it’s so much easier to avoid situations like that entirely.

But I saw this all the time on the tennis tour. Picture this: young, talented players facing veterans who’ve spent years fine-tuning their skills, learning every trick in the book. Instead of embracing the fact they were beginners in a new league, they’d tell themselves, “I should be winning this.” And when they lost? They’d walk away with a list of excuses, anything to avoid admitting – just maybe – they weren’t ready for the big leagues yet.

I was guilty (very guilty) of this, too. And trust me, it doesn’t just put you under massive pressure – it holds you back from learning, from evolving, from actually moving up.

Here’s what I realized about it:

1/ Being the underdog is inevitable. If you’re growing, you’re bound to end up out of your depth. It’s a sign you’re pushing yourself – that’s a good thing.

2/ What really separates people who rise quickly? They embrace their place and get obsessed with learning. They can admit, “Yeah, I’m outmatched right now,” and instead of feeling defeated, they treat every moment as an opportunity to pick up new moves, study every detail, and – eventually – master the game.

Let’s face it, humility is tough, and nobody wants to say, “I’m far from perfect and maybe don’t yet deserve to win.” But if you do, it’s a superpower. That’s the mindset that lets you take real feedback, drop the excuses, and keep growing.

The Psychological Barrier of Comparison

We grow up being taught to be self-aware. But that often means constantly sizing ourselves up against others, ranking where we fit in – which usually brings out our worst.

Comparing yourself to others? Not inherently bad. It’s human. The problem is, it’s almost always followed by something worse: lying. Lying to yourself, lying to others that you’re as “successful” as everyone else around you. That you, too, can afford a Mercedes, that you’re running a multi-million-dollar business, that you could win Wimbledon.

And here’s where it gets toxic: eventually, these lies eat at you, causing people to quit because they can’t live up to expectations that they built up in their own heads.

We’re also taught to have high expectations, to reach for more, to believe “anything is possible.” Mostly, I agree. Being ambitious is a wonderful thing – it lets you dream big, take risks, and break the status quo. But it’s equally important to remember that hard work, while essential, doesn’t guarantee success. (That’s something they don’t tell you growing up.)

And social media? It amplifies “Underdog Syndrome.” It feels like everyone else is “crushing it” (ugh, I hate that phrase), founders are posting non-stop wins, athletes are flaunting medals. We see it and think, “If I’m not on their level, then what’s the point?”

The point, ironically, is trying. If it were only the end goal that mattered, we’d all pack it up as soon as we started. Life’s about the journey. Goals, ambitions, plans – they’re what make life thrilling. Using other people’s success as a marker for your self-worth? That’s the trap.

Let’s talk about a trick that’s as old as public speaking itself: imagining people in their underwear. Ever wondered why it works? It’s not just about calming nerves; it’s about bringing intimidating people down to your level.

When you walk into a room full of people who seem more experienced or successful than you, it’s easy to put them on a pedestal. You start thinking, “I have to be as good as them – or at least look like it.” But the reality is, that pressure is entirely self-imposed, and it’s likely blocking you from actually connecting with them or learning from the situation.

Imagine them in their underwear, and suddenly, they’re just human. You’re reminded that they’re not perfect either. They’ve got their own insecurities, their own lessons they’re still learning. This mental trick lets you lower those expectations, take a breath, and just give it your best – mistakes and all.

In business, this mindset shift is huge. When you stop holding yourself to the imaginary standards you’ve created, you’re free to start taking risks and learning. You’re not there to impress everyone; you’re there to grow. And if it takes picturing everyone else in their underwear to do that – hey, whatever works.

Here’s the Takeaway: Embrace Being the Underdog

Next time you’re the least successful person in the room, embrace it. Look around and realize every mistake you make is a stepping stone that gets you closer to where you want to be – if you’re willing to learn from it.

Stop holding yourself to imaginary standards based on the successes of others. Stop thinking you need it all figured out. Instead, learn. Absorb everything you can. Treat every situation as a chance to level up without worrying about “looking the part.”

The most successful people – whether founders, Olympians, scientists, or leaders – admit they’re still growing. The ones who keep moving forward are the ones who own their mistakes, learn from them, and keep growing.

If you enjoyed this, then follow along with our progress at Cancha (my brand), connect with me on LinkedIn (more business insights). 

Until next time!

Jack Oswald