Playing to Win vs. Playing Not to Lose — Lessons from 12U Baseball

After every tournament, I take a day to reflect on what I saw — the growth, the gaps, and the mindset beneath it all. This week, three boys said something that revealed a lot about how kids think about competition, confidence, and the difference between playing to win and playing not to lose.

Lou LaMedica

Oct 14, 2025

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Playing to Win vs. Playing Not to Lose

I like to wait at least 24 hours after the last game to let my thoughts crystallize. Where do we need to improve? How can we set the team up for better success? What themes in our chemistry are starting to emerge?

The thought that stuck with me after this weekend’s tournament was about desire.

We’ve been talking a lot about having the desire to win, the drive you need when you step on the field. But three boys said something this weekend that made me pause.

“I didn’t want to let the team down and lose.”

That’s not “I want to win.” That’s “I don’t want to be the reason we lose.”

It’s a subtle difference, but a huge one.

At twelve years old, these boys are right at the edge of that psychological shift where fear of failure starts to outweigh love of competition. You can almost see it. That moment when a player starts playing to protect instead of to create.

But baseball doesn’t reward caution. It rewards freedom, confidence, and trust. The willingness to take your swing even when you might miss.

When you play not to lose, your body tightens up. You guide the ball instead of driving it. You aim your throw instead of trusting it.

When you play to win, you move with purpose. You attack. You compete with belief instead of hesitation.

That’s the mindset we’re building—shifting from avoiding mistakes to creating success.

Because it’s not just a baseball lesson. It’s a life lesson.

You can’t build something great by tiptoeing around the edges. You have to lean in, take the swing, and trust yourself enough to go for it — the same kind of fearless energy I wrote about in Please Be Kind, Rewind

“Winning isn’t everything. Wanting to is.”
— Catfish Hunter

That’s what I hope they learn from all this. That playing to win is really just another way of saying: believe in yourself enough to try.

“Know what’s enough. Build what matters.”

You might also like:

Please Be Kind, Rewind – A reflection on youth, optimism, and the movies that remind us to stay light on our feet.

The Courage to Say It Out Loud – Why saying what we expect — of ourselves and others — is the first step to growth.

The Boredom of Building a Business – On patience, repetition, and finding pride in the process rather than the result.

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Lou LaMedica

Playing to Win vs. Playing Not to Lose — Lessons from 12U Baseball

Playing to Win vs. Playing Not to Lose

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