Balancing Act: Why Losing Is Good For You

By Heidi Stevens
Chicago Tribune

WWR Article Summary (tl;dr) Sam Weinman, an editor at has a new book out that seems pretty interesting. It’s called “Win at Losing: How Our Biggest Setbacks Can Lead to Our Greatest Gains.” Weinman interviewed a variety of folks famous for their epic losses to find out how and why they picked themselves up after defeat. And more importantly, how those defeats served them.

Chicago Tribune

It’s not unusual, particularly in Chicago, to find sports reporters writing about losing. (Hi, Bears!)

But to read a sports guy waxing poetically about the benefits of it? Not so common.

That’s just what Sam Weinman, an editor at and a longtime hockey and golf writer, has done with his new book, “Win at Losing: How Our Biggest Setbacks Can Lead to Our Greatest Gains” (TarcherPerigree), and it’s instructive reading for anyone who wonders how to cope with defeat, at work, at sports, at life.

Weinman was inspired to write the book after watching his 10-year-old son melt down after losing a tennis match, and it’s filled with insights for parents who hope to help their kids not just lose gracefully, but bounce back stronger and smarter.

“My argument is that we end up learning more from our failures than we do from our successes,” Weinman writes. “And I maintain we’re better served listening to those who have lost constructively than those who’ve simply won. These are the strongest people we know, and in a society still uneasy with failure, their insights are more valuable than ever.”

With that in mind, Weinman interviewed a variety of folks famous for their epic losses, Michael Dukakis, who won just 111 delegates to George H. W. Bush’s 426 in the 1988 presidential election; Susan Lucci, nominated and passed over for 18 Emmys (she won the 19th); golfer Greg Norman, famous for his 1996 Masters collapse, about how and why they picked themselves up after defeat, and how those defeats served them.

“The point isn’t that you should strive for mediocrity,” Weinman writes. “But … uninterrupted success is a fantasy. … Losing is something not only that we should tolerate but also that we need.”

Weinman weaves in perspectives from psychologists, including Stanford University’s Carol Dweck and Jonathan Fader, author of “Life as Sport.” Fader talks about “contingency management”, our ability to deal with unforeseen challenges, and argues that shielding yourself from failure is a mistake.

Imagine taking the same route to work every day, Fader offers, and discovering one day your route is blocked. A person adept at dealing with setbacks quickly navigates an alternate route. “Imagine a world where for every negative result, we just sat in our car not moving,” he says.

Unanticipated defeats make us more agile. We don’t do a bang-up job of rewarding, or revering, losers, though.

“No one sets out to be a good loser, in the same way that no one sets out to be an ex-husband,” Weinman writes. “I used to think of losing as one would curing a hangover or avoiding prosecution: If you’ve achieved a level of proficiency at it, you probably ought to consider what that says.”

But watching his kid go to such a dark place after defeat, and hearing his wife say, “My God. He’s you.”, inspired Weinman to search for ways to embrace a growth mindset, which doesn’t just view losing as an eventuality, but also as an opportunity.

“People in a growth mindset don’t just seek challenge,” Dweck tells Weinman. “They thrive on it.”

One of the things that makes losing so difficult to endure, Weinman contends, is how bleak life seems in its wake. Kids, especially, lack the life experience and perspective to remind them that feeling is temporary. It’s hard to remember there will be another game, another test, another audition. Even as adults, we forget there will be other job offers, other dates, other elections.

“In some form or another,” Weinman writes, “there’s always a new race to run.”

Reading the stories from the other side of famous defeats, as well as the psychological benefits of those defeats, is incredibly useful.

Weinman interviewed Ralph Cox, a hockey standout who broke his ankle in a game one month before tryouts for the 1980 Olympic team. He talks to Weinman about feeling embarrassed, as though he’d let a lot of people down, and bitterly disappointed not to be at the Olympics with his teammates.

“Having to find my way out of the darkness was at times a very painful experience,” Cox tells Weinman. “But 95 percent of it was incredibly powerful. Failure, if done properly, is the magical opportunity to create success and happiness.”

What more could we ask, for our kids and ourselves?

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