The Strategy Paradox — Thoughts from the Court, Vol. 1

This is the first piece in a series I’ve been meaning to write for a while. Twenty-odd years of playing tennis at a reasonably high level has left me with a pile of lessons that I keep running into, over and over, in completely different contexts — building communities, working in frontier tech spaces, trying to do things that haven’t really been done before. I figured it was worth writing them down.

There’s a thing that happens to tennis players at almost every level, and it goes something like this: you’re in a match, maybe a set in, and something starts to go wrong. Maybe your backhand feels off, or you double-faulted at the worst possible moment, or you’ve just gotten broken and your mind starts spiraling into everything that’s broken about your game right now. Your grip. Your toss. The way you’re not getting low enough on the ball. You’re inside your body, inside your strokes, inside your mistakes, and the more you dig around in there, the worse everything gets.

The conventional wisdom — and I heard this a lot growing up — is that the solution is more technique work. Get the fundamentals so deeply grooved that they become automatic, and then you’ll be free to think about other things. Earn your way to strategy. It’s not totally wrong, but I think it misses something important, and it took me years to understand what that was.

The thing it misses is this: strategy is not a reward you get for having good technique. Strategy is actually the escape hatch *from* your technique. When you shift your attention from what your body is doing to what you’re trying to do on the court — like, genuinely, what’s the actual plan here, what are you trying to build in this point, where do you want the ball to go and why — something interesting happens. Your body, which is significantly smarter than you’re giving it credit for, quietly gets on with the job. The self-consciousness that was strangling your strokes starts to loosen. You’re no longer performing tennis at yourself. You’re just playing.

I think about this a lot when I watch Medvedev. He just lost in the finals at Indian Wells a few days ago, but on his way there he beat Alcaraz, who is playing some of the best tennis in the world right now. Medvedev is not the most aesthetically satisfying player to watch — his game doesn’t look the way tennis is “supposed” to look. His strokes are awkward in ways that coaches might flag. But the man is a chess player on a tennis court. Every ball he hits is in service of a structure, a plan, a set of ideas about where he wants the point to go and what he’s trying to force you into. And because of that, his “imperfect” technique works at an extraordinarily high level. His body learned to serve the strategy.

That’s the relationship I’m pointing at. A good strategy — a coherent system for what you want to be doing, a genuine theory of the game — creates the conditions for technique to develop around it. You don’t have to have everything figured out before you’re allowed to think big. In fact, thinking big is often what unlocks the physical development in the first place.

I work in a space where people are constantly trying to look around corners; building things in bleeding-edge tech fields, trying to get novel ecosystems off the ground, operating in areas where there isn’t really a playbook yet. And I see the same pattern show up constantly. People who are waiting until their fundamentals are solid before they start thinking about strategy. Waiting until the product is polished, the community is bigger, the funding is secured, the timing feels right. Getting so deep inside the mechanics of what they’re building that they lose the thread of what they’re actually trying to do and why.

The instinct makes sense. Nobody wants to be caught playing big chess moves with a game that isn’t ready. But I’d push back on the idea that you sequence these things — first technique, then strategy. In my experience, it’s more like a loop. You need enough strategic clarity to give your work direction, and then the work builds the capability, and then better capability opens up new strategic possibilities, and so on. Waiting for permission to think about the bigger picture is a good way to stay stuck in your head forever.

The question worth sitting with, whether you’re on a tennis court or trying to build something genuinely new, is: what am I actually trying to do here? Not what strokes do I need to hit, not what mechanics do I need to fix — but what’s the game I’m playing, and what does it look like when it’s working? If you can hold onto that, even loosely, you give yourself something to move toward instead of something to be afraid of.

More to come.