Win at Losing: How Our Biggest Setbacks Can Lead to Our Greatest Gains

Win at Losing: How Our Biggest Setbacks Can Lead to Our Greatest Gains

by Sam Weinman


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An engaging, inspiring exploration of the surprising value of setbacks—and how we can use them to succeed

As an award-winning sports journalist, Sam Weinman has long studied the ripple effects of losing. But as a father of two competitive boys, he struggled to convince them that failing—whether losing a hockey game or bombing a math test—can actually be a critical part of success. So he sought out the perspectives of men and women who have turned significant setbacks into meaningful comebacks—and sometimes even new careers—to illustrate how we can not only overcome defeat but grow stronger from the experience.

Blending firsthand interviews and advice from professional athletes, business executives, politicians, and Hollywood stars with expert analysis from leading psychologists and coaches, Win at Losing reveals how renowned figures—from Emmy Award–winning actress Susan Lucci to golfer Greg Norman and politician Michael Dukakis—have prevailed and even triumphed in the aftermath of loss, humiliation, and rejection. In showcasing the ways our most difficult moments can be turned into powerful growth opportunities, this lively and moving guide asks readers to redefine what constitutes success and failure, and offers an essential blueprint for harnessing the power of setbacks to achieve what we want in life.

Product Details

ISBN-13: 9780143109587
Publisher: Penguin Publishing Group
Publication date: 12/20/2016
Pages: 256
Sales rank: 736,092
Product dimensions: 5.70(w) x 7.60(h) x 1.00(d)

About the Author

SAM WEINMAN is the digital editor of Golf Digest. Prior to that, he was a senior writer for The Journal News in Westchester County, New York, where he was honored with multiple national writing awards for his coverage of the PGA Tour and the National Hockey League. His work has also appeared in USA Today, Golf World, Yahoo! Sports, ESPN the Magazine, and Sports Illustrated. A graduate of the University of New Hampshire, he lives with his wife and two sons in Rye, New York, where he coaches multiple youth sports teams. To learn more, check out his website,

Read an Excerpt

The greatest glory in living lies not in never falling,

but in rising every time we fall.


The most important sporting event I ever attended was a kids’ tennis match on an August afternoon. This might seem odd coming from a sportswriter who has covered World Series and Stanley Cup Finals and dozens ofmajor golf championships. But none of those events involved my kid. And none led me down this curious road of talking to everyone from professional athletes to CEOs to presidential candidates about their most crushing defeats. That’s the road that led me here.

  But first there was a tennis match on a quiet late-summer day. There was no press. There were only a handful of spectators. And the only real drama came at the end when my oldest son essentially lost it.

  I should explain: Charlie is a pretty good tennis player. Approaching eleven, he has everything down—the two-handed backhand, the open-stance forehand, the emphatic little grunt with every stroke. Charlie couldn’t tell you the reason one grunts when playing tennis. But he knows that Rafael Nadal grunts, so the conversation endsthere. 

  This is how it usually works with him. About a year ago, Charlie talked us into getting him a blue Nike headband like the one Nadal wears, and now whenever he misplaces it, he reacts as if he’s missing a kidney. “Where’s my headband?” he’ll ask before a match, tearing frantically through the house. “I can’t play without myheadband!”

  Over the courseof that summer, as Charlie would punctuate forehand winners with Nadal uppercuts, the other kids around the tennis court took to calling him Rafa. Charlie ate it up—so much, in fact, that if in mixed company I dared to call him anything else, I might as well have announced he still wet the bed.

  “Rafa,” he’d correct me.

  “Right,” I’d say.“Sorry.”

  When it came time for our club’s junior tournament, Charlie progressed through the early portionof the ten-and-under bracket with enough ease that he began thinking ahead to the final. We both did, actually, although outwardly I was saying all the right“dad” things: Respect your opponent; one match at a time; it’s important to just have fun. In the semifinal, when he matched up against a timid, freckly kid named Jake, Charlie bounced onto the court confidently, perhaps thinkingthat if he wrapped up the win with enough time to spare, he could sneak in a swim and a candy bar before dinner. Seated on the deck overlooking the tennis courts, my wife, Lisa, and I made small talk with Jake’s mom and feigned indifference through the first part of the match. Oh, are they keeping score? How cute! We anticipated a short match.

  But as play unfolded, nothing went right. Charlie placed backhands into the corner, and Jake hunted them down, sometimes even passing Charlie with a winner of his own. Serving, never a strength for my son, was now an ordeal, with Charlie at onepoint forfeiting an entire game by sending eight consecutive balls into thenet. On the deck, Lisa continued to indulge Jake’s mom in conversation, but I couldn’t hear them anymore. I was entranced. As I watched my son, I could seehis anxiety level rise—the hurried tosses, the twitchy fiddling with his racket, the occasional look heavenward when he sailed another shot long, as if God had suddenly taken interest in a ten-year-old’s tennis match and was siding squarely with Jake.

  By the final game, Charlie was flat-footed and waving passively at the ball. On the final point his forehand bounced before the net and onto Jake’s side, and Jake briefly weighed whether he should play it. It didn’t matter; the match was over intwenty minutes. Charlie lost 6–1.

  When Jake approached the net with his hand extended, Charlie shuffled forward to weakly reciprocate, looking past his opponent the whole time. Then he tore off his headband, flung his racket at my feet as I approached, and ran toward theparking lot.

  “Charlie!” I hissed in a sort of scream-whisper, the same type of urgent yet polite tone you might use to ask someone to fetch you a roll of toilet paper. “Come back!”

  Charlie turned toward me, his face streaked with tears.

  “I’m never playing tennis again!” he said. “That’s it!”
  “Stop, Dad,” hesaid. “It’s not funny.”

  It went on like that for a little while, Charlie swearing off tennis, me summoning some of mybest “It’s only a game—you’ll learn from this” material. Though I still hadn’t talked him out of retirement, I eventually convinced him to gather his racket and head to the car while I went to find Lisa, who had said good-bye to Jake and his mom and was now waiting for me under the awning by the tennis court. Lisa and I have been married for fifteen years and have been friends since the fifth grade. She knows all my looks, and I know most of hers, and as I walked toward her, she offered a faint smile in the “What have wegotten ourselves into?” vein. Then she finally spoke.

  “My God,” she said. “He’s you.”

So this book began with a tennis match. In watching Charlie unravel over something so insignificant, I started to think about howlearning to lose is an acquired skill, like juggling or parallel parking. It contradicts our most basic nature because everything in our DNA has taught us to want to win and hate to lose. After all, at one point in our history, winning was about more than tennis matches. It was about securing food and shelter and not letting the neighborhood pack of wolves make off with one ofyour kids. You’ve heard that Vince Lombardi line “Winning isn’t everything. It’s the only thing.” The context was football, but for a great portion of human existence, it could have been describing the simple struggle to survive.

  Now, though, we lose and usually live to tell about it. We lose in sports, and we lose in ourcareers, and we lose out on that house with the perfect backyard we were certain we were going to get. Some of us are losing our hair, although we’dprefer not to talk about that. Over the course of any given year, we probably lose a thousand different ways, and as painful and inconvenient as those losses might be, we still have a say in how we handle them. We too often overlook that last part.

  This is a truth I’ve come to appreciate not only as a father of two sports-mad boys but also as someone who’s had his own frequent dalliances with failure. My wife’s contention that Charlie in the teary aftermath of his tennis match is a miniature version of me is true, but only to an extent. I still struggle with losing in its various forms: in men’s league hockey games, in golf matches for fivedollars, and as an editor when I see the competition come up with a story we don’t have. My authority in writing this book does not stem from the graceful and admirable ways I’ve lost in my life but rather the opposite. I’ve thrown my racket and slammed my fist on my desk, and on one occasion I slung my varsity jacket into a puddle of mud after a bad pass cost my high school hockey team our season. Once, stuck in a newspaper job, I was awaiting word about a plum job I was on the short list for getting. It was my birthday, and Lisa and I were headed out the door for dinner. When the email came that the job went to someone else, I sat down at our kitchen table and cried.

  The difference now is I also see that losing can serve in ways winning never can. Losing hastaught me and toughened me and forced me to address the very shortcomings that got me in trouble in the first place. That bad pass I made at the end of my junior year in high school inspired me to get stronger and fitter, and it led to a senior year in which I emerged a different player. That plum job I didn’t get was inspiration to develop the skills that led to an even better opportunity later.

  Looking outside myself, I’ve also come to realize that the people I’m most impressed by are notthe ones who appear to float through life but those whose weaknesses and failures are exposed in all sorts of undignified ways and yet they emerge stronger as a result: golfers who’ve blown tournaments, politicians who’ve botched elections, the bookstore owner who has struggled to pay his bills for decades and has only recently begun to turn a profit. What I’ve found is that the people who’ve approached their failures honestly and constructively are often able to point to tangible benefits of those losses. The impact of this can be profound: The more we can embrace the upside of losing, the healthier our perspective toward whatever is in front of us, the less encumbered we are by fear.

  Although my interest in how we handle losing began with a personal challenge, I saw it as a challenge that permeated every segment of our society. And it was in recognizing the thread between my family’s modest struggles and the bigger, bolder storiesthat exist elsewhere that I decided to dive in headfirst. I sought out Olympians and politicians, entertainers and Internet startup CEOs. Their versions of losing vary—lost games, failed political campaigns, businesses and careers dissolved in flames—and may seem unrelated at first glance. But there are similarities as well, and it was upon consulting a wide swath of experts that I learned there is not only an art to losing but a great deal of science, too. I saw there is a way to not only tolerate setbacks but also use them as a foundation for future success—to win, if you will, at losing.

  I’d love to tell you I contemplated all this while driving away from the tennis courts that day, but more likely I was thinking about dinner and whether I needed to stop for beer. But the image of Charlie’s frustration lingered. I had taught my son a forehand and a backhand, and he knew exactly where to stand when receiving at 30–15. Yet there was still much for both of us to learn about coping with theswirling emotions that come with defeat.

No one sets out to be a good loser, in the same way thatno one sets out to be an ex-husband. 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.

  You may recall Super Bowl 50, when the Denver Broncos upset the Carolina Panthers, and Carolina’s star quarterback, Cam Newton, was so despondent he walked out of his postgame press conference. The next day he explained his reasoning, “Show me agood loser and I’ll show you a loser.”

  I’ve come to abhor that sentiment to the point that I now think being a good loser is exactly what we should aspire to be. Being a good loser does not denote some hapless resignation. It implies perspective and resilience and the quiet confidencethat the world will not crumble around you just because of a fleeting setback.

  There are all kinds of stories about athletes whose abundant desire to win carried over to the most mundane tasks. At airports, Michael Jordan would bet his teammates whose bag would shoot out of the carousel first. Jordan was said to revel in winning, less because he needed to prove his baggage claim prowess and more because, like Cam Newton, he didn’t want any more experience with losing than he absolutely needed.

  Trivial as it sounds, Jordan was doing himself a disservice. There is in fact merit to this sort of experience, and he should know. As a high school sophomore, Jordan was famously cut from the varsity basketball team, and he channeled that disappointment into a competitive fire that burned for decades. Later, when his Chicago Bulls stumbled in the playoffs each spring against the more experienced Detroit Pistons, Jordan used the lessons from those losses to help transform the Bulls into a dynasty.

  The Bulls would win six NBA championships over the next eight years, and Jordan, who also won an NCAA title and two Olympic gold medals, would become known as the consummate winner in basketball, if not all of sports. But success brought complications as well, many of which persisted into retirement. Jordan became so obsessed with winning and so uneasy with losing that he struggled to find a comparable outlet now that he had hit middle age and was incapable of replicating the same level of success he had as a player. The writer Wright Thompson had rare access to Jordan and his inner circle for a 2014 profile in ESPN the Magazine, and he depicted the basketball legend in the years following his retirement asunfulfilled and restless.

  “There’s no way to measure these things, but there’s a strong case to be made that Jordan is the most intense competitor on the planet. He’s in the conversation, at the very least, and now he has been reduced to grasping for outlets for thiscompetitive rage,” Thompson writes in “Michael Jordan Has Not Left the Building.” “His self-esteem has always been, as he says, ‘tied directly to the game.’ Without it, he feels adrift. ‘Who am I? What am I doing?’?”

  By Thompson’s account, Jordan’s model was unsustainable. Beyond deriving outsized satisfaction from the games he won, he had so distanced himself from the sensation of failure that he had no road map for how to react when his post-Bulls career proved rocky. To Dr. Jerry Brodlie, a noted family psychologist in Greenwich, Connecticut, this Jordan was an extreme version of the teenager who thinks he can do no wrong and then struggles mightily once hedoes. “It’s like he’s this golden kid who develops an inflated sense of self,”Brodlie says. “Ultimately, these are the kids who have a really hard time when whatever makes them special is taken away.”

  In his celebrated commencement address at Kenyon College in 2005, the late author David Foster Wallace detailed the perils of placing unhealthy value in something as tenuous as money, beauty, or glory. “Worship power, you will end up feeling weak and afraid, and you will need ever more power over others to numb you to your own fear,” Wallace said.

  The point isn’t that you should strive for mediocrity, and heaven help me if my argument is based on the pitfalls of becoming a multimillionaire icon. But both Brodlie and Wallace arrive at the same place: uninterrupted success is a fantasy. The absence of certain humbling elements in our lives makes us more vulnerable in the long run. From there it stands to reason that losing is something not only that we should tolerate but also that we need.


Excerpted from "Win at Losing"
by .
Copyright © 2016 Sam Weinman.
Excerpted by permission of Penguin Publishing Group.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
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