Learning to Win at Winning

I recently helped facilitate a leadership training session with school leaders. During our time together, we posed two simple questions: What is a recent leadership win? and What is a current leadership struggle?

A pattern emerged immediately. When leaders spoke about wins, nearly every response centered on their team or their school. Success was collective, shared, and outward-facing. When we turned to struggles, the shift was stark. Almost every answer became deeply personal. Leaders spoke candidly about their own shortcomings, blind spots, and areas for growth.

When we pointed this out, the room grew quiet. The realization landed.

Reflection matters. Continuous improvement matters. But so does recognizing your own victories. Too many leaders are experts at accountability and amateurs at celebration.

I know this because I live it. I struggle with personal praise, with public recognition, with allowing myself to simply receive a compliment. A therapist could likely trace that back to my childhood. Still, I have learned this is not just my issue. It is common among leaders across fields.

At the core of it lies perfectionism. Others see what we achieved. We see what we missed. What looks like a strong performance from the outside often feels incomplete from the inside. A win becomes a checklist of what still needs fixing rather than something worth pausing for.

The Winter Olympics recently began, and while flipping through events, I caught a Hershey commercial featuring several Olympic athletes. Each spoke about chasing gold, about the singular focus required to win on the world’s biggest stage. Then their loved ones appeared on screen, telling them something far more important. They were proud of them regardless of medals. Loved for who they are, not what they produce. Gold, they reminded them, was just a bonus.

That message struck me. It is one many leaders need to hear.

We must learn to enjoy our victories in real time. Not as fleeting relief before the next problem, but as meaningful evidence that our work matters. Every major achievement is built on a series of smaller successes along the way. Those moments are not distractions from the goal. They are the energy that sustains the journey.

I was watching the luge this morning when commentators highlighted an athlete competing in his fifth Winter Games. Over four previous Olympics, he had consistently placed in the top ten, even earning silver, but never gold.

Think about that. Two decades at the highest level of sport. Year after year among the best in the world. Yet it would be easy to reduce his career to one missing medal.

We do the same thing to ourselves.

I hope you reach the “gold” in whatever you are pursuing. More than that, I hope you recognize the wins that get you there. And most of all, I hope you understand that many people are already proud of you, whether you finish first or tenth. Showing up consistently, doing meaningful work, and moving toward your purpose is leadership in its truest form.

So I will end where we began.

What is one of your leadership wins?

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