For Investment Leaders: Why You Should Learn to Love Losing

The first time I met Dr. Daniel M. Zimet, he told me the story of his best-ever handball match. His story changed my life, and it can empower investment leaders to improve the trajectory of their organizations. It goes like this…

By the time the 1997 three-wall Nationals came around, Zimet had already lost eight times to his nemesis Kendall Lewis, a ranked professional handballer. “If you were to see us side-by-side, the results wouldn’t surprise you. Kendall was built like an NFL tight end. I’m scrawny and scrappy,” Zimet said.

This fateful match started at five on a Saturday afternoon. The first game went the same way as many others between the two players. Zimet ground out bread-and-butter points while Kendall made spectacular shots. But unexpectedly, Zimet eked out a 21-20 victory in game one after an hour of play. Lewis found his rhythm in the second game and prevailed 21-7, sending the match into a tiebreaker. 

As it started to get dark, the venue’s lights came on and the players passed the second hour of grueling play. The crowd swelled. The fans became so boisterous that the event director stopped matches in the adjacent courts. Those fans added to the ones already watching this incredible match. Beer was flying in the stands. Kendall served for the fourth time to win the match point. Trying something new, he hit an overhand serve. Zimet’s return was weak and short, a perfect opportunity for Lewis to hit a low-kill shot.

More than 20 years later, as we sat in his office, Zimet recalled what happened next like it was yesterday:

“I reached deep into my depleted well of strength and sprinted as fast as I could to the front of the court, where Kendall’s match-ending shot seemed to fall in slow motion. At full sprint and stretch, I caught up to the ball an inch from the ground and hit the perfect shot — a flat kill. I rolled over on the concrete to break my speed. On my knees, I squeezed both hands into fists and screamed at the top of my lungs. The crowd’s roar was so overpowering that I couldn’t hear my voice.”

His voice trembled as he retold this story. I could swear his eyes grew watery. But what happened next is a bit strange. He told me the rest of the story nonchalantly.

“He was down 9–10 and failed to score on his next serve. Then, Kendall served an ace.”

“Wait, you lost?” I asked. “How was that your ‘best moment’? What about all your wins?”

I couldn’t understand how a world-class athlete could be elated by defeat.

But Zimet then explained his rationale: “Measurable goals can impede self-motivation. Those who focus on mastery — rather than on the scoreboard — are the biggest winners in the long run. That time, I played to the absolute best of my abilities.”

This match changed Zimet. From then on, he knew he belonged amongst the best in the game.

“Every victory stands on that match’s shoulders,” he told me. “That match, that point, and that loss solidified my quality as a player, a competitor, and a person, making it the most important moment of my career as an athlete.”

Of course, he loves to win, but Zimet – a sports psychologist — defines success in terms only a sports psychologist could. He focused on mastery over ego, the importance of relationships and community (“The crowd’s roar was so overpowering that I couldn’t hear my voice”), the meaning of sport as a meritocracy, and the importance of engagement and flow. To him, all these concepts came together that day on the court.

His theory became an epiphany for me. I asked myself: What if leaders could develop a similar mindset and apply it to their organizations?

Zimet’s story was the spark that started the project that became my forthcoming book, The Psychology of Leadership, available for pre-orders. It put me on a path of discovery. I spent four years investigating new ways to apply psychology to leadership. I plowed through hundreds of books and articles in scientific psychology. What I learned has been life-changing and worth sharing with the world. 

I will be discussing these concepts at CFA Institute Live 2025 in Chicago in May. In next week’s post, I will discuss the hidden trap sabotaging your decisions.