Home Thinking Aloud Losing Isn’t The Worst Thing: A Lesson In Purpose 

Losing Isn’t The Worst Thing: A Lesson In Purpose 


by Jason Caldwell, founder of Latitude 35 and author of “Navigating the Impossible: Build Extraordinary Teams and Shatter Expectations

These days, I give a fair amount of keynote speeches. I love telling my stories and having the audience be able to see themselves in them. My favorite part of my talks is directly afterward, when audience members are inspired to come up to me and share a quick anecdote about an experience they had that evoked similar emotions to a story I’ve told.

It’s amazing what stories people choose to share with me in that moment. Veterans of war, mothers of loss, and conquerors of cancer have all found their way to me. Personal stories of happiness and sadness, hope and despair, all because people felt a connection with me during the 60 minutes I stood on the stage. I find this to be the most rewarding part of my job.

However, there’s another group of individuals who come up to me from time to time, eager to share what they believe to be a common bond between us. These people are the more aggressive, type-A personalities who want to talk only of victory.

In an effort to identify with me, these individuals will say things like, “Like you, I never lose.” Or even more often, “I could totally identify with you up there. I hate losing, too. It’s literally the worst thing.”

For those people who choose to share their utter hatred and unfamiliarity with losing, I politely nod but am skeptical of their comments. When people say they never lose, I believe they’re either not telling the truth, or they choose to disengage from life in ways that keep them safe from failure. Either way, I can’t identify with them.

Losing Is a Healthy Part of Life.

I have nothing in common with men or women who say they hate losing or that they’ve never lost. I lose all the time. Not only do I lose all the time, but I also constantly put myself in positions where losing isn’t just a possibility but a probability — sometimes even an inevitability. To me, losing isn’t the worst thing. It’s not only part of life, but it’s also a very healthy part of life, one that’s vital to individuals and teams who strive to be the best version of themselves.

Losing gives you a benchmark, a place to reconsider. You learn more in losing than you do in winning because your injured pride is desperate to find the remedy, and this opens your mind to a true education. We don’t want to lose, but for anyone trying to win, losing is always part of the process.

So forget about losing for a second and focus on the true enemy of your success. The absence of an endeavor or challenge that’s worthy of your efforts and passion is truly the worst thing. Failure to find that “something greater” than yourself is the true culprit that undermines your success as a human.

Said simply: The worst thing is not losing but lacking purpose.

Leadership Lesson: Have You Found Your Purpose?

Matt Brown was a teammate of mine during our world record-setting row across the Atlantic Ocean, and he was an integral part of that success. Matt and I had a history, as we rowed together in Philadelphia after college. I had always respected Matt; he was a tough and tenacious athlete. But that wasn’t the reason I called him one spring day to assess his interest in being the fourth and final teammate of our ocean rowing team.

Though social media, I discovered that Matt had recently attempted to qualify for the Olympics in the men’s single, arguably the toughest event in rowing. He had trained for years in hopes of making it to the Olympics, but this year he fell short and lost in the finals. Matt wasn’t going to the Olympics.

I called Matt because I knew him well enough to know he was in a dark place, not because he lost, but because he was likely unsure of what to do next. For a man of Matt’s caliber, that was truly the enemy of his success. I called Matt to offer him a purpose.

With Matt on the team, we went on to win. It was the best decision I made that year.

What will be yours?


Jason Caldwell is the founder of Latitude 35, a leadership training firm that operates around the globe. He works with top organizations — including Nike, Booking.com, Columbia Business School, and the Haas School of Business — and delivers speaking programs to packed crowds at Fortune 500 companies and universities worldwide. A professional adventure racer, Caldwell currently holds over a dozen world records across five continents. His new book is “Navigating the Impossible: Build Extraordinary Teams and Shatter Expectations“.


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