The Lost Art of Figuring It Out

The junior player I coach has been losing in the first round of tournaments. Same mistakes, every time.

After the first loss, we addressed it. Broke down what went wrong, worked on it, prepared. They went back out. First round. Lost again. Same mistakes.

So we addressed it again.

The problem wasn’t technique. It wasn’t preparation. They weren’t thinking on their own. Every lesson was just another answer collected. And collecting answers isn’t the same as learning to think.

I’ve been coaching long enough to know the difference between a player who wants to get better and a player who wants to be made better.

This was the second one.

The frustrating part is that tennis doesn’t even allow me to be that person. Coaching during a match isn’t allowed — no timeouts, no signals from the sideline, no adjustments from a coach. Once the match starts, the player is entirely on their own. So when something goes wrong — and something always goes wrong — they have to read it, adjust, and execute a new plan in real time, without help. For older players, this is just the nature of the game. For a lot of younger players, it feels like being cut off. They’ve grown up in a world where the answer was always one ask away, and when that lifeline disappears, they freeze. The issue isn’t their tennis. It’s that they’ve never had to solve a problem without someone handing them the solution.

Asking for help is good. It’s necessary. But at some point the answer has to come from you.

I remember being stuck on a video game level for days. Dying every run. Same spot, same outcome. Frustrating enough to put the controller down — but never long enough to quit, because I hadn’t figured it out yet and that was the whole point. Each time I came back I tried something different. Adjusted. Got a little further. Eventually I got through it. Not because someone told me how. Because I stayed in it long enough to work it out.

Auto-save removed that loop entirely. Fail now and nothing happens. There’s no consequence to sit with, no reason to analyze what went wrong. And if that wasn’t enough, you can now find a guide online that tells you exactly how to beat any level, any boss, any puzzle. No need to figure it out. The answer is already there.

The internet did something similar, but quieter. It’s not just that answers are easy to find — Google or ChatGPT will hand you one in seconds. It’s that finding an answer has replaced the experience of working one out. Think about GPS. You can follow directions perfectly for years and still have no idea how to get somewhere on your own, because the route was always provided and the mental map never formed. Always-available answers do the same thing to thinking. You get the destination but skip the navigation. The ability to move from confusion to clarity — to sit with a problem, turn it over, and work your way through — only develops through practice. If every question resolves in thirty seconds, that practice never happens. You don’t just lack information. You lack the experience of thinking.

What this creates is a generation that’s genuinely afraid of uncertainty. Not failure exactly, but the feeling of being stuck — of sitting in a problem without an immediate way out. That discomfort is so unfamiliar it reads as an emergency. And when something feels like an emergency, you freeze. You ask someone to fix it. You wait.

But here’s what nobody tells them: failing isn’t really failing unless you keep doing it.

Failure is information. It tells you exactly what isn’t working, which is the most valuable data you can have. Every player who has ever figured something out mid-match — no coach, no timeout, no lifeline — did it by reading their failures in real time. Not avoiding them. Not waiting for someone to decode them. Sitting in the discomfort and using it. That’s not a talent. It’s a learnable skill. And if the younger generation is just now starting to develop it, they’re not behind — they’re beginning. The friction they’ve been missing is still available to them. They just have to stay in it instead of running from it.

The junior player will figure it out. I’m not worried about them. At some point they’ll stop collecting answers and start finding them. When that shift happens, they’ll improve faster than they ever have — not because they got better at tennis, but because they got better at thinking.

That’s the opportunity inside all of this. Not a problem to fix. A skill to build. And the first time they sit with something hard, work their way through it, and come out the other side on their own — that’s not a small thing. That’s everything.