We Don’t Learn More from Losing. We Learn More from Interrogating.

By Paddy Upton

Why does losing make you stronger than winning?

It doesn’t.

That’s a lovely idea. But it’s also, in most cases, rubbish.

The notion that we learn more from failure than from success has been floating around sport and leadership circles for years. And I’m not convinced it holds up. In fact, I strongly disagree.

Here’s why that idea probably exists: most people, after they succeed—what do they do? They celebrate. The deal lands, the scoreboard looks good, the champagne comes out. Job done.

And after they fail? Most people interrogate. They stop, reflect, review, dissect the decision, the preparation, the execution, the mood in the room—everything. There’s a post-mortem.

So where does the learning happen? In the celebration, or in the interrogation? It’s not rocket science.

It’s not the win or the loss that teaches you. It’s what you do afterwards.

The best in the world do something different. They interrogate both. Success and failure get the same treatment. Both are reviewed. Both are taken seriously. And from both, they ask the same two questions:

What did I do well? What did I learn from this?

Not just after a mistake. Not just after a blowout loss. But after the wins too.

Because whether you win or lose, you likely did most things right, most of the time. And it’s important to know what those things were—so you can keep doing them. There are usually only one or two things you got wrong. And if you’re lucky, those might still be hiding in plain sight… even when you’ve just won.

That’s the real danger.

Sometimes, we get something wrong and still walk away with the trophy. We misread a moment, or someone else covers for us, or the opposition makes more mistakes than we do. The scoreboard rewards us, the room cheers—and in the noise, we miss the lesson.

Other times, we do nearly everything right… and still lose. The bounce of the ball, a decision that doesn’t go our way, the odds swinging the other side. The scoreboard says loss, but the performance? Maybe one of our best.

The lesson is there in both. If we’re willing to look.

Which is why learning shouldn’t depend on whether you won or lost. It should depend on your willingness to pause and ask better questions.

Winning and losing offer equal lessons. The difference lies in whether you choose to engage in the post-mortem—or just reach for another beer or tequila.

Because how you celebrate a win, or debrief a loss, might have more impact on your long-term performance than the result itself.

And when we let the outcome determine whether we reflect or not—we’re leaving half the learning on the table.