Derek Jeter on Failure: “Don’t Let the Speed Bump Become a Roadblock”

Long before he stood in front of 70,000 people at Michigan Stadium as the commencement speaker, Derek Jeter was already known for something bigger than baseball. He was The Captain. A five-time World Series champion, Hall of Famer, and cultural icon, Jeter’s greatness wasn’t just measured in stats or titles—it was built on professionalism, poise under pressure, relentless consistency, and an unwavering team-first mentality.

He didn’t just play for New York. He gave the city—and fans everywhere—belief and a blueprint for honoring the craft, showing up for the process, and giving everything you love to the game and your teammates.

This past weekend, the Yankees legend returned to the place where his college dreams began—briefly—before the majors came calling. Enrolled at the University of Michigan in 1992, Jeter left just a year later after being drafted by the Yankees. But standing at the Big House decades later, his message to the 2025 graduating class had nothing to do with batting averages or championships. It had everything to do with choices, purpose, and the courage to fail.

“How you approached today, and every day, is a choice—your choice. Your life will ultimately be framed by the choices you make,” Jeter said.

In a world obsessed with perfection and success, Jeter kept it real—talking about failure not in distant, abstract terms but in vivid, personal ones.

“Failure. Failure is essential. If I can promise you one thing for certain: You will fail,” he said.

“The bigger the dream, the bigger the risk. What is the price if you don’t take the risk? If you don’t commit to the dream? You might end up overmatched. But maybe you won’t. I failed publicly. I failed miserably. There were days I literally cried because I was so bad. My first season as a professional, I made 56 errors. And for the non-baseball fans, that is hard to do intentionally... But you, me, every one of us has to learn to deal with failure. I wouldn’t have had the success without the failures.”

In a world that celebrates highlight reels and picture-perfect outcomes, Jeter offered something far more powerful: permission to fail—and a mandate to keep going when we do.

“It’s your job to make sure that a speed bump doesn’t become a roadblock.”

Too often, when things don’t go our way—when we suffer defeat or fall short—we start contemplating the exit ramp. We tell ourselves maybe we’re not built for this. Maybe the dream was too big. Maybe it’s time to quit.

But what if failure is just the beginning? What if adversity isn’t a verdict—but a teacher?

“Surround yourself with the right people,” Jeter added. “While you may fail on your own, it’s nearly impossible to succeed alone.”

For us as leaders, coaches, and high performers, this is more than motivational fluff—it’s strategic wisdom. One of the greatest competitive advantages we can build, both for ourselves and our teams, is the willingness to wrestle with failure and lean into it—not retreat from it.

Because it’s easy to play it safe. But are we truly living when we do? It’s easy to stay comfortable. But leadership isn’t about avoiding failure—it’s about engaging with it. Choosing to see it not as a signal to stop, but as a moment to grow, improve, and transform.

There will be days we question ourselves. Moments that shake us to the core. Days and nights when we need to pause, cry, breathe more deeply, rest, recharge, sit in the sadness and simply be still. And that’s okay. That’s what makes us human. These moments allow us to fully feel the failure—but also give us a profound opportunity: to choose not to be defined by it.

It’s in these moments—the ones we’d never choose, but life hands us anyway—that the true test of leading ourselves and others begins.

And it’s where we must decide: Will we let the speed bump become a roadblock, or will we find a way to keep moving forward?

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