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On Making Mistakes

DC Citi Open, summer 2025. I watched some of the best tennis players in the world duke it out in my backyard. The energy was electric. Tennis found its way back into my heart.

I went home and even picked up one of my old rackets and started swinging.

For most of my life, I'd been a novice tennis player - a tourist with a tennis-obsessed father but no real skills of his own. Just the drive to compete on court.

So at 32, I picked up tennis. Not as a hobby. I wanted to get good.

And boy, was I terrible.

The Illusion of Competence

Over six months, I devoted myself to weekly coaching sessions, consumed matches obsessively, and tried every quirky training regimen I could find. What struck me most wasn't how much I had to learn. It was how many bad habits I'd picked up along the way - habits that had lulled me into believing I knew the game, when I clearly didn't.

Here's what makes false competence so seductive: it feels like knowledge.

My forehand looked decent to me. I could rally. I won points against friends. That veneer of capability gave me just enough confidence to avoid real scrutiny. Why question something that seems to work?

But "seems to work" and "actually works" live in different universes.

The moment I stepped on court with a coach, the illusion shattered. My grip was wrong. My footwork was lazy. My swing - the one I'd rehearsed thousands of times - was encoding failure into muscle memory.

That gap between perceived competence and actual competence is humbling. And it extends well beyond the court.

The Hidden Cost of Standing Still

False competence does something insidious: it creates the appearance of progress while keeping you frozen in place.

You're not a beginner anymore, so you don't have a beginner's humility. But you're not actually good, so you can't operate at a higher level. You're stuck in a kind of purgatory - too experienced to admit you don't know, too unskilled to compete with those who do.

I've lived in that space. In tennis. In relationships. In work.

The mental gymnastics required to maintain the facade are exhausting. You avoid situations that might expose the gaps. You nod along in conversations you don't fully understand. You double down on the wrong approach because admitting error feels like admitting fraud.

And here's the kicker: everyone around you can see it. The only person you're fooling is yourself.

Tennis mirrors life in ways that feel familiar:

  • You make more mistakes than things you get right
  • You lose more than you win
  • There's always an inner voice trying to control outcomes
  • Success most commonly arises when you're just having fun

The game won't let you hide.

The Wisdom in Being a Fool

I've made several mistakes in life. Too many to count. I've been too blunt, too naive, too insensitive, too sensitive. Too much or not enough.

Otto von Bismarck said only a fool learns from his own mistakes - the wise man learns from the mistakes of others. Alas, I am only a fool.

But maybe that's the wrong framing.

Einstein put it differently: a person who never made a mistake never tried anything new. Every innovation, every breakthrough, every great achievement sits on the other side of risk, trial, and error.

The distinction isn't between making mistakes and avoiding them. It's between honest incompetence and false competence.

Honest incompetence says: I don't know, but I'm willing to learn. False competence says: I can't admit I don't know, so I'll pretend I do.

One path leads to growth. The other leads to stagnation dressed up as stability.

The Pattern of Real Growth

The bad habits I built in tennis felt like knowledge until a coach showed me they weren't. The mistakes I've made in life felt like catastrophes until the next one came along and the last one quietly faded.

The pattern is the same:

  1. You show up
  2. You get it wrong
  3. You adjust
  4. You get it wrong again, differently this time
  5. And somewhere in that cycle, if you're paying attention, you get a little better

But here's what the pattern requires: the courage to be visibly bad at something.

Not bad in private. Not bad in theory. Bad in front of a coach who watches your form fall apart. Bad in front of colleagues who see your first draft. Bad in a way that cannot be hidden or rationalized away.

That vulnerability is the price of admission. And it's steep.

It means letting go of the identity you've built around "knowing things." It means sitting with the discomfort of being a beginner again. It means admitting that the techniques you've relied on - the ones that got you this far - might be the very things holding you back.

Most people can't pay that price. So they stay put. They keep using the wrong grip. They keep having the same arguments. They keep making the same strategic errors, year after year, because acknowledging the mistake would mean acknowledging they've been wrong all along.

What the Alternative Looks Like

This may serve only as a reminder to myself: it's okay to be a beginner. To start over. To try new things and be terrible at them.

It's okay to say "I don't know how to do this" instead of pretending competence you don't possess.

It's okay to unlearn muscle memory, even when it feels like regression.

It's okay to ask for help, to seek coaching, to admit that your current approach isn't working.

Because the alternative - standing still while pretending the bad habits are skill - isn't stability. It's decay with better PR.

Real competence is built on a foundation of acknowledged incompetence. You can't fix what you won't admit is broken.

So yes, I'm a fool. I learn from my own mistakes because those are the only lessons that seem to stick. I get things wrong more often than I get them right. I restart at 32 in tennis, I may restart again, at various ages in my career, friendships, my athletic or creative pursuits.

But at least I'm moving. At least the mistakes are new ones.

At least I'm not standing still, gripping the racket wrong, telling myself this is as good as it gets.