The Hidden Power of Investing in Loss

In a world obsessed with instant results, there’s something deeply uncomfortable — and profoundly powerful — about choosing the slower path. The one that doesn’t guarantee quick wins. The one where you might struggle more now to grow stronger later. This is the mindset behind what Josh Waitzkin calls “investing in loss.”

Waitzkin, a chess prodigy turned martial arts champion, explains that progress often requires us to deliberately step into discomfort. To take a few steps back. To be willing to look bad, lose short-term battles, and unlearn rigid habits — all in service of something far greater: mastery.

It’s a hard sell. Especially in with kids youth sports. And not so much to the kids... but to us as parents.

We’re wired to want the scoreboard to validate our choices. We cheer when our kids play on the "top team," score goals, or get more playing time. We associate winning with progress, and struggle with stagnation. But the truth is: some of the most important growth happens beneath the surface, during the awkward, inefficient, sometimes humbling stretch between knowing and becoming.

Ask any great performer — in sport, music, business — and they’ll tell you: there was a season when they had to rebuild from the ground up.

Maybe it meant fixing a flawed movement pattern. Or playing with more skilled teammates and feeling outmatched for a while. Maybe it was about shifting their focus from output (stats, wins) to input (discipline, mindset, skill acquisition).

In each case, they temporarily sacrificed certainty for growth.

They invested in loss.

One of the most powerful developmental mindsets is what’s called “shoshin” in Zen Buddhism — beginner’s mind. It’s the ability to approach any challenge with openness, curiosity, and a willingness to fail forward. Kids actually do this naturally… until adults start keeping score.

As parents, coaches, and mentors, our role isn’t to shield kids from struggle — it’s to frame struggle as meaningful, and guide them through it. That means valuing progress over polish. It means recognizing that playing on the "best team" right now isn’t always best for their development. Sometimes the more powerful move is being in an environment where they have to lead, adapt, learn.

Investing in loss doesn’t mean losing for the sake of it. It means being strategic about what matters most in the long run.

It’s trusting that the player who struggles to keep up today might, with the right support, become a more complete, confident athlete tomorrow.

It’s accepting that development doesn’t always feel good — but it’s worth it.

It’s remembering that the best stories don’t come from comfort zones — they come from growth zones.

So the next time your child feels behind, or the team isn’t dominant yet, or the short-term outcome doesn’t match the effort — pause. Look closer.

They just might be in the middle of an investment that pays off for years.