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in: Advice, Character, Podcast

• Last updated: September 30, 2021

Podcast #646: How to Win at Losing

Losing stinks. Nobody wants to suffer defeat in a game, flunk a test, or get passed over for a promotion. Losses can feel like stinging humiliations, insurmountable setbacks, like the end of the world; they can even push us to quit pursuing something we love. And yet losses can be the most instructive and meaningful parts of our lives, and be central to our ultimate success.

My guest set out to study and explain these underappreciated upsides of getting bested. His name is Sam Weinman, he’s a sportswriter, and he shares what he learned in his book, Win at Losing: How Our Greatest Setbacks Can Lead to Our Greatest Gains, as well as in today’s episode. Sam and I begin our conversation with how losing is typically a lot more interesting than winning, the difference between losing and failing, and how you can lose without failing, as well as fail without losing. Sam then illustrates the lessons in humility, growth, personal responsibility, and resilience that can come from losing by sharing the stories of famous people who dealt with famously big losses, including golfer Greg Norman, soap star Susan Lucci, presidential candidate Michael Dukakis, and speed skater Dan Jansen. We end our conversation with how Sam’s study of how to turn loss into gain has influenced his own children and the way they deal with setbacks.

Good insights here both on how to deal with your own losses as well as how to help your kids deal with theirs.

If reading this in an email, click the title of the post to listen to the show.

Show Highlights

  • Why losing is more interesting than winning
  • The difference between losing and failing
  • How you can lose without failing, and fail without losing 
  • Greg Norman’s magnificent failure at the Masters Tournament  
  • How losing can soften people’s rough edges 
  • Michael Dukakis and the 1988 presidential election 
  • Susan Lucci, the Daytime Emmys, and what she learned from her decades of losses
  • Why Dan Jansen fell on the ice at the Olympics 
  • Process vs. results 
  • What Sara Hess can teach us about finding new mountaintops 
  • The losing Columbia football team of the 80s 

Resources/People/Articles Mentioned in Podcast

win at losing book cover by sam weinman.

Connect With Sam

GolfDigest.com

Sam’s website

Sam on Twitter

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Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness podcast. Losing stinks. Nobody wants to suffer defeat in a game, flunk a test, or get passed over for promotion. Losses can feel like stinging humiliations, insurmountable setbacks, like the end of the world. They even push us to quit pursuing something we absolutely love, and yet losses can be the most instructive and meaningful parts of our lives and be central to our ultimate success. My guest set out to study and explain these unappreciated upsides of getting bested. His name is Sam Weinman, he’s a sports writer, and he shares what he learned in his book Win at Losing: How Our Greatest Setbacks Can Lead to Our Greatest Gains, and he shares some of those insights with us today on today’s episode of the AOM podcast.

Sam and I begin our conversation with how losing is typically a lot more interesting than winning, the difference between losing and failing, and how you can lose without failing as well as fail without losing. Sam then illustrates the lessons in humility, growth, personal responsibility, and resilience that can come from losing by sharing the stories of famous people who dealt with famously big losses, including golfer Greg Norman, soap star Susan Lucci, presidential candidate Michael Dukakis, and speed skater Dan Jansen. We end our conversation with how Sam’s study of how to turn loss into gain has influenced his own children in the way they deal with their setbacks. Good insights here on both how to deal with your own losses as well as to help your kids deal with theirs. After the show’s over, check out our show notes at aom.is/winatlosing.

Alright, Sam Weinman, welcome to the show.

Sam Weinman: My pleasure, thank you for having me.

Brett McKay: So about three or four years ago, this was I guess 2016, you published a book called Win at Losing, and it’s all about how to be a good loser, what it’s like to lose, and the lessons you can learn from losing and the upsides of losing. I’m curious, what kickstarted you on that project to explore loserdom?

Sam Weinman: The original genesis for me was just a challenge I was having with my boys. I have two sons, now they’re 15 and 12, and obviously when I embarked on this they were younger, but even then it was just very apparent to me that they didn’t understand or see any value whatsoever in losing, and both competitive kids, competitive athletes, and we had a series of sort of comical meltdowns in various settings, and it just became very apparent to me that this was an area that not only they, but everyone can really stand to embrace, is that in every loss there is a lesson, in every loss there is an upside and an opportunity to respond in a more constructive way. And so that was the idea, and ultimately it was this concept of, look at all of these amazing, impressive people who have lost in spectacular fashion, and look at how they responded and look at how they are able to point to those episodes as real growth moments for them. And not all of them had these triumphant comebacks from those losses. Some of them, the losses are what define them, at least in the public’s eye, but they… Even those people can still say yes, there was a lot of good things that came out of this.

Brett McKay: Well, and you’re also a sports writer, you write about golf, so you encountered losing in your career on a regular basis, and we’ll talk about one golfer who lost monumentally. But you saw it, you saw this regularly.

Sam Weinman: 100%, and I would say one of the things that was very apparent to me, and it’s still very apparent to me throughout my sports writing career, is a game ends or a tournament ends or whatever, and some of you would go into the winners’ locker room to talk to the winners, some of us would go into the losers’ locker room and always felt like the story about the losers was more interesting because they were a bit more introspective and a bit more willing to discuss what went wrong, which is just a hell of a lot more compelling than, “You know, we executed what we wanted to, we came in, we really wanted it… ” All those cliches from winners.

People who win are happy, and rightfully so, but they don’t really plumb the depths of what happened as much as you do when you lose. And so that was definitely a big part of it as well, I just felt like those were the most compelling stories and continue to be. And the other part is, I’m a sports coach, I’m a youth sports coach with my boys, and it just feels like… And I’ve said this a hundred times. Your practices after losses, your next session after a loss, is far more constructive and everyone is much more engaged than after you win. Because after you win, everything’s great, there’s nothing really to talk about, but after you lose, there’s a lot of things to go over and build upon.

Brett McKay: Right, and you make that point, that losing… Success can actually get in the way of getting better because you think, well, we won, we don’t have to do anything. With losing, though, it really causes that self-reflection and to look at, what are my weak points so I can get better at that?

Sam Weinman: Exactly, exactly. And there’s a million examples of people who have had uninterrupted success early on in their lives, and when they are faced with setbacks, which everyone is, they struggle more than the people who have the typical bumps in the road and have to scratch and claw their way out of it. You have guys who are on the fast track at some point, and then something goes wrong and they’re not equipped to deal with it.

Brett McKay: So in the beginning of the book, you make a distinction between losing and failing, and I think often in our just common conversation, common vocabulary, we can conflate the two. They’re the same, losing and failing is the same. But you think it’s important to recognize the difference. So first off, what is the difference, and why do you think it’s important to make that distinction?

Sam Weinman: Yeah, I think… To me, the best way to explain the difference between losing and failing is that losing is just an event, it’s just a fact, it’s something that happened. Failure is an interpretation of what happened, and it’s somewhat a reflection on poor execution or inability to execute or some sort of poor effort. And the reason why it’s important to distinguish between the two is that sometimes you lose and it’s not really your fault; things just happen a certain way, and you need to recognize that there’s not much point in beating yourself up over something that just went the other way. Whereas a failure is an opportunity to examine and analyze what you did wrong, where you fell short, so that you can adjust accordingly. And it’s possible to lose without failure, and it’s also possible to fail without losing, which I can explain.

That sounds sort of vague, but to me it’s like we have all of these things that go our… Go against us in life and… Which we would characterize as a loss and… Sometimes it’s something that we did that we can learn from and sort of beat ourselves up over. But there’s also times when it’s like, “You know what? I’m not gonna beat myself up over this ’cause this wasn’t… This wasn’t on me.” Not to oversimplify that this current moment in time, but look at this, look at this global pandemic; look at all of the… Look at all of the hardship that has resulted from this period; people losing jobs and businesses are failing. Well, a lot of those… Again, businesses are suffering, I should say, just to not confuse it.

Well, people are losing jobs in large part because of an event that’s outside of their control, so that’s a loss. When you talk about a failure, if someone loses their job because they screwed up X, Y and Z, it’s important to note that is that difference.

Brett McKay: No, yeah, I think if anyone’s played sports, they understand that distinction where how you can lose but not fail, but fail but not lose. I’ve had those games. I remember in high school where… In football that we played really sloppy, it was just terrible, but we still ended up winning ’cause the other team just played sloppy. And so we won, but it really it was a bad game, we failed; we didn’t play up to our potential. But then we had those games where you did everything right, but the other team just did a little bit better and there was nothing else you could do.

Sam Weinman: Right. And that’s a concept that I talk about in the book, and for young kids that’s a very difficult concept to understand. You walk into a locker room after losing a game 2-1, and you might have actually played one of your best games of the year, and again, that’s a loss not a failure. You did everything, almost everything, right. And to your point, there’s tons of times when, “You know, yeah, we won, but it wasn’t because we did anything that well; there’s so many things that we can improve upon. And there’s a lot of things that we need to address here.” And again, that’s a really difficult concept for… For really anyone to really wrap their heads around, but especially when they’re young.

Brett McKay: So when you set out to research and write this book, you interviewed… Or, yeah, you got interviews with all these people, famous people who lost in spectacular ways; and they’re known for losing. When you made these reach-outs, did a lot of people… Were a lot of the people hesitant to talk about it? Or were most people pretty open about it?

Sam Weinman: There were definitely people who I reached out to who were not open to doing it, and either they didn’t respond or they respectfully declined and… Which is fine. The famous example is Bill Buckner, who as you probably know is the first baseman for the Boston Red Sox, ball rolls through his legs, 1986 World Series; he’s synonymous with this egregious error in the worst possible setting. I reached out to him, and he declined through the Red Sox. I don’t begrudge him for doing it, or for declining, but I would argue and from what I’ve read about him is that there’s a great story to tell about how that episode shaped him.

And there was a lot of pain there, so I don’t want to say it would be an easy story to tell, but there was a number of people like that. And then the people who did ultimately agree to talk to me were people who basically buy into the premise, who bought into what I was selling. And there was a little bit of flattery from me. The pitch was, “Hey, I wanna talk to you about why you’re such a loser.” The pitch was, “You are someone who is known to have sustained a really significant loss in your profession or in your life, and my perspective is that there’s a lot that people can learn from how you handled it. Would you be open to discussing this?” And of course, you butter ’em up in that way and they’re like, “Yeah, that sounds great, thank you so much,” and so the conversation went from there.

Brett McKay: Well, and what’s interesting too is that is seems like in the past, I’d say, decade, this idea of talking about failure has become more acceptable. Maybe it’s something people don’t like to talk about but it’s become more socially acceptable. But you make this point that, yeah, we’re more open about talking about failure, but we don’t… Sometimes we don’t do it in a really productive way. What do you think is going on there?

Sam Weinman: Well, a couple of things. I think that you’re right, it’s become kind of like a corporate cliche; you know, losing is, you gain from failure, and your business fails, and then there’s something to be said for that. And I think the reason why that’s great in concept but it’s not always great in execution is that people are glossing over the real hard parts. They wanna point to their failure and wanna point to everything that went wrong, but they’re not really willing to do the work and the real investigative work into their shortcomings to really grow from it.

Brené Brown, the author, has talked about it as gold-plating grit, meaning you’re willing to point to all of the benefits of your setback without actually going through the real hard work of unpacking it and learning from it. And the metaphor that I use for it is someone who goes to the gym and they walk on the treadmill for 10 minutes at really low speeds, and then they get off and pat themselves on the back for a killer workout. Well, yeah, they went to the gym and they worked out, but they didn’t really do the work to really gain anything from it. So there’s gotta be some pain, there’s gotta be some discomfort in that process for you to actually grow from it. And so I think when we talk about people who don’t really confront failure in a constructive way, that’s what we’re talking about.

Brett McKay: Gotcha, alright, so let’s talk about some of these famous people who lost, and you start off the book with someone from your domain of golf, and it’s Greg Norman, and you use him as a way that how losing can teach us humility. So for those who aren’t familiar with Norman’s career, can you give us a thumbnail sketch of it, and then what was his magnificent failure? Or, well, not failure, we’ll say loss.

Sam Weinman: Sure. Well, actually, I think it’ll be both in this instance, but so Greg Norman, one generation earlier was the premier star in golf. Great-looking guy, immensely talented, had some incredible, incredible runs, that topped the world ranking in golf, and in many ways, he was sort of the poster boy for success. But in some ways he also was not a very approachable guy. He was, he’s just a better golfer than you, he’s better looking than you, way wealthier than you, not very identifiable to the average person. And then along the way, he had some really notable collapses in major championships. And the biggest one, and really kind of the, I would say the defining moment of his career, was the 1996 Masters.

It was the tournament he wanted to win the most, he had opportunities to win earlier in his career, and in ’96, he takes a six-shot lead into the final round. And the famous moment is, he’s preparing for the next day, he’s walking out of the clubhouse Saturday night, and a writer goes to him and says, “Greg, not even you can beep this up.” And sure enough he does. He blows the Masters, he falls apart on the front nine, and he’s defeated by Nick Faldo, who’s kind of his rival of the time. And the reason why that was such a important moment was not because he lost, but because in that moment, this incredibly impressive, sort of hard to associate or identify with character became immensely human. Because everyone just ached for him. You watch the final nine of that broadcast when it was already apparent he was gonna lose, and it’s painful to watch, because this guy’s dream was dissolving right before him.

And his press conference afterwards, he was very honest about how much it hurt, and he got this huge outpouring of support. And so the reason why I always think of Greg Norman as such a great loser is because here’s a guy who had all these amazing successes throughout his career, and the real moment of connection with the public was when he lost. And for me personally, I was in college at that point, and I’d just started getting into golf, and that was the moment I was like, “My God, this game is so painful, and this guy, I feel for this guy,” who you normally wouldn’t think you could feel for a guy who’s a multi-millionaire superstar athlete, and so that was the story I wanted to tell, and Greg was very, very accommodating and willing to talk through every part of that process.

Brett McKay: And when you talked to him, and this has been decades since that happened, has he come to peace with ever not, not ever winning the Masters? He won all these other tournaments, but the Masters, the green jacket. He never got it. Has he come to peace with that?

Sam Weinman: Yeah, ’cause he had to, right? It just, if it wasn’t that day, it was not soon after that he realized, “I’m never gonna win one of these, and so what am I gonna do? Am I gonna… Am I just gonna consistently lament and rue everything that went wrong? Or am I going to see what I can sort of gain from it and learn from it, if not as a professional golfer, but as a person and as a business man,” and so I think he came as close to as peace with it as you can.

Brett McKay: And as you talked to him, how do you think it’s that experience of not achieving that goal that he had, how did that influence his post-golf career? Or and even not his career, but just him as a person, did he become more approachable? Is that one of the things that happened?

Sam Weinman: Yes, 100%. I think again, it was a real humbling moment, he became a much more approachable, probably a little bit more willing to laugh at himself and make fun of himself. I mean, Greg Norman appeared naked in the ESPN body issue at age whatever it was, 61 or something like that. There’s a little bit of hubris there still, but it’s also a little bit of humility, like, “Listen, I’ve already been exposed in other ways earlier in my career, this is no big deal.” And professionally, as a businessman he’s got a big line of clothing and wine, he’s got a huge sort of multi-faceted business, and I think he’s had a lot of successes, but also some failures. And he always says, “Because I failed in such spectacular ways on the golf course, I’m willing to be more flexible with setbacks and failures in other aspects of my life.”

Brett McKay: One of the stories too, if he would have won the Masters, he would have been one of the first Australians to win the Masters. But then I guess a couple years ago, one Australian guy actually won.

Sam Weinman: Yes.

Brett McKay: And Norman kind of… He’s a really competitive guy. If I were Norman, it’d be easy to see like, “I’m gonna be resentful of this. That could have been me.” But it seemed like Norman, he didn’t do that, he was really supportive of this guy.

Sam Weinman: Yeah, well, again, that’s like to your earlier question, right. It’s like, did he come to peace with it? Well, at that point, when Adam Scott wins the Masters in 2013, Greg Norman is well past his prime as a player and he realizes, “Well, I’m not gonna win one, and the mature and sort of admirable thing to do is throw my arms around this guy and celebrate his successes,” which is not something that you can easily do, but a lot easier to do when you’ve had some practice as a loser.

Brett McKay: And something that, I think what he did, what allowed him to do that, and you talk about this too, is the way Norman talked about his failure. I think after he lost, his family was just despondent, and I think he said to them, he was like, “Hey, look, yeah, I didn’t get it, but look, I’ve made so much money hitting a little white ball. So we’re fine, we’re gonna be okay.” He did some re-framing to help them, I don’t know, help them digest the loss.

Sam Weinman: Well, 100% and that’s a big theme throughout the book and throughout all of these stories is with every loss, there is inevitable pain, but in order to move forward, you gotta find… You’ve got to frame it in a way that’s palatable to you, and so for him, it was that, it was look at all you… Look at all the things that have gone my way in life, am I really gonna complain about this? It was also saying, “Here are the lessons I can learn from it.” And I think, again, going back to this idea that not the most approachable guy beforehand; through this loss became far more relatable than ever before and was embraced in ways that he never would have been had he just cruised to victory.

Brett McKay: Alright, so another famous “loser” you talk about is Michael Dukakis, who famously lost the presidential race to George H W Bush, I guess that was in ’86, that was…

Sam Weinman: ’88, 1988, yeah.

Brett McKay: ’88, ’88, so some of our listeners are probably too young to remember the 1988 presidential election, I was probably eight at the time or six, so what… So let’s talk about Dukakis, what was his career like before he ran for president, and then just talk about his presidential campaign and why it became synonymous with losing?

Sam Weinman: Yeah, well, to answer your last question first, it became synonymous to losing because he’s kinda like the poster boy for just getting completely blown out, like it was… He was really a one-sided, one-sided loser in that election, and sort of humiliating… You look at all the elections over recent years, there are usually a couple of points margined one way or the other, and Dukakis, it was never even close. So he’s sort of this guy, even if you are young and you don’t really know it, he sort of synonymous with blow-outs, and so how does a guy look at himself knowing that? So that’s one of the reasons why I was intrigued talking to him, and I actually, when I set up to talk to him, I didn’t really know the full story of his career prior to that point. And what’s interesting is that he was a guy who his big goal was to be governor of Massachusetts, went to Harvard, had some early success in government, ran for governor of Massachusetts, won the election, and then four years later, he lost the Democratic primary for re-election and it’s never happened.

You’re the incumbent governor and he was defeated by a challenger and he talks about that as being like an absolute gut punch, the real… Far worse than the presidency, because he was voted out of office, and it was a real sort of referendum on everything he had done wrong in office. And the amazing about that is, he has four years to think about it and think about the next steps, and he takes a look at what he did in his first go round as governor and what he could have done better, and scratches and claws his way back to run again, and he wins this time. And he says, “I was a much, much better governor in the second go round, in large part because I learned from all the things I did wrong in my first term. I wasn’t merely as interested in other people’s opinions, I kinda just pushed through my agenda without really listening to other people, and it was really detrimental.”

And because he was such a better governor the second time around, learning from his mistakes, he has great success, he starts to get a national reputation, ends up winning the nomination for the Democratic primary in 1988. And again, early on in that campaign, midway through the summer, he actually was beating George H W Bush in a lot of the polls, and it looked like he was gonna win, and then we can talk about all the things that went wrong from there.

Brett McKay: Yeah, so yeah, what did go wrong? He had it… It looked like he’s gonna win, but then it just went south real fast.

Sam Weinman: Yeah, well, and the interesting thing, back to this idea of losing versus failing, well, what happened in that campaign was like that was a real turning point in national politics, because George H W Bush, his campaign went… Got pretty dirty. They went after Dukakis in a pretty savage way, there were some campaign ads they ran about his crime record that were probably unfair subjectively or I would say objectively speaking. And there was an episode where Dukakis was riding on a tank and he wore a helmet and he just looked comically bad, it was a bad look. And they pounced on him and they just hammered him and think about national politics now, all this stuff seems pretty tame, comparatively speaking; back then, it was pretty vicious.

And you would think all these years later that Michael Dukakis would say, “Yeah, the reason I lost is they fought… They fought dirty and it was unfair, and that’s why I lost.” And that would be the way a lot of people would frame the loss, and he was like, “Actually no, they did what they needed to do, and I didn’t respond the right way. I could have responded to all those things, and I could have found a better way to answer a lot of the charges that were lobbed against me and I never did, and that’s on me.”

And that’s a really impressive stance to take because, again, a lot of what we talk about in the book is understanding when is it someone else and when is it you, and to be able to point to your own shortcomings and be really honest about that is a really… It’s a really healthy thing to do, and I would submit it’s a really impressive thing to do, because it shows you’re always… You’re always looking to be better. And even now, he’s 80-plus years old, his willingness to accept that and acknowledge that is, I think, is a really good lesson for the rest of us.

Brett McKay: Yeah, I mean, I think you use him as an example, you bring in this research about growth mindset, fixed mindset from Carol Dweck, it seems like Dukakis had a growth mindset. He never thought, “Well, I lost, that’s the way it is, there’s nothing I can do about it.” It was, “Well, I lost, there’s something I could have done, maybe I could’ve have done some things differently.”

Sam Weinman: Correct.

Brett McKay: And that’s a good attitude to have, and it’s a hard… Look, it’s really hard to do, it’s really hard to take the blame for a loss, particularly on, at such a magnificent level, but you can definitely grow if you do.

Sam Weinman: Totally, and I just think blaming… My experience and my view is that blaming very rarely leads anywhere productive, and so the more that you can just look at your part of the equation and you feel like there’s a little bit of power in that, like, here’s what I could have done, here’s what I should have done, it’s a lot better than saying all these forces conspired against me.

Brett McKay: So one of my favorite stories you highlight in the book is the story of Susan Lucci, which is interesting, ’cause I’m not… She’s a… For those of you who are not familiar, she’s a soap opera star. I never watched soap opera, except when I was sick in elementary school and it was on after The Price is Right and that was the only thing on. But her story really… It was captivating. So for those of you who don’t know, who is Susan Lucci and what’s her story about failing, or losing?

Sam Weinman: Yeah, it’s funny, I feel like I’m dating myself with all these stories, ’cause they are a little bit more my generation, which it doesn’t sound like we’re that far apart, but if you’re… Right now, Susan Lucci’s name doesn’t mean much, but she was this soap opera actress, not that I was a soap opera viewer myself, but she… The one thing you knew about soap operas was that there was gonna be an Emmy Awards, and that Susan Lucci was gonna be nominated, and she was gonna lose. And it was like… It was comical. Literally 19 times she was nominated for a Daytime Emmy Award, and she lost, to the point where it was sort of like a pop culture joke. People would refer to person X or team X as “the Susan Lucci of this.” The Buffalo Bills, when they lost four straight Super Bowls, were the Susan Lucci of football, and you can go down the line, that was a running joke.

And so when I was researching the book and thinking about the book, I’m like, I wonder what Susan Lucci actually thinks about people being called “the Susan Lucci of this” because of their proficiency in losing, and it turns out she had a really great story to tell, and it was like, there was a number of levels to it. One was, first of all, asking her, “In your view, you were nominated for all these Emmy Awards and you lost. Why was that the case? What did you learn from it?” And she said, “Actually, there were things I learned from it. I realized that in talking to judges and learning from judges, there were some things that I had done in my performance and in my acting that rubbed people the wrong way and rubbed judges the wrong way.” She was overly dramatic, whatever those elements were. She actually saw there were parts of it that were off-putting to people who saw her, and even as this larger-than-life star, exorbitantly wealthy and a bit of a diva, she was like, “Well, you know what, I gotta do something about this, because it’s obviously an error that I need to improve upon.” So she did that.

The other thing was, she had a family and kids and a son, ironically enough, who is a very good high-level competitive golfer, played college golf and made a go as a professional, and he had his own ups and downs trying to make it on tour, and he said, “You know what? Amazingly enough, I learned how to stomach a lot of the adversity that I’ve faced trying to make it on tour from my mom, and watching her approach to her profession and, in her own way, being kicked in the stomach every year and getting up and going to work the next day and trying to be better.” And it ended up being really instructive to him. So it was a bit of a symbolic story there, like the ultimate loser, what can you learn from her, and in her case, there were some real tangible lessons both for her internally and also for the people around her.

Brett McKay: Did she have a sense of humor about it…

Sam Weinman: Yeah.

Brett McKay: Did it really pain her to not win?

Sam Weinman: I think both, I think both. I think it hurt, I think she talked about how she would go to these Emmy Awards and hope for the best and get dressed up and they would have the camera on her as soon as they announced the winner, and she’d have to have that fake smile that you always see, and she’s like, “That sucked, that was really hard.” So it did really hurt her, but she also had a great sense of humor, like she was on Saturday Night Live as a host, and the only reason she was the host is ’cause she was the consummate loser and people knew her for that. And she did a bunch of commercials that sort of poked fun at her. So you had to have a sense of humor, and again, going back to that Greg Norman idea of humility, that’s… Having a sense of humor about these failures in your life is the ultimate sign of humility, and she obviously exhibited that.

Brett McKay: Well, and because she had that growth mindset, she actually took the feedback and tried to get better, even like 19… She was a veteran at this point. At that point, she could have just rested on her laurels, but she continually tried to get better. The result, she ended up actually winning.

Sam Weinman: She did. She won in, I think it was her 20th try, or… Again, when did… Think about someone who you are willing to embrace at that point, a great success that everyone wanted to celebrate, is when Susan Lucci finally won a Daytime Emmy. And again, none of us knew anything about Daytime Emmys or cared about it, but you just knew this person kept going every year, kept losing, and then finally broke through and won. It’s a great story that people can feel really good about.

Brett McKay: So one of the gut-wrenching stories that you told was the story of Dan Jansen, who was one of the greatest speed skaters in history, like he was setting world records, he was winning all these world championships, but when it came to the Olympics, he would just choke magnificently, and he wouldn’t even medal. What was going on there? Why would he perform so well in every other competition, but when it came to the Olympics, he would just fall apart?

Sam Weinman: Yeah, a lot of things were going on, and I think, looking back at the book, it’s been three or four years, I think the Dan Jansen chapter ended up being probably one of my favorites because there are so many layers to it and it touches on a number of things we already talked about, but for one thing, the real tragic story that is part of Dan Jansen’s larger story is that in 1988, when he was the clear favorite to win the 500-meter speed skating event, the morning of the race his sister died. She had leukemia, they were very close, he literally talked to her on the phone that morning and she passed away right before he started the race.

And they show him on national TV, the race starts, and he falls a few strides into the race, understandably so, he’s just kind of a ghost and not really there. And then two days later, this is the 1000 meters, even worse in a way, he is leading the race, he’s gonna win for his sister, all these things, and in the final stretch he falls again and, again, doesn’t medal, doesn’t even come close, and… Heart-wrenching stuff. Four years later, the memories of his sister are still there, but he’s still back to being the top speed skater in the world, had won World Championships, but still hadn’t won an Olympic medal, goes to the Olympics in Albertville, France, and same thing, doesn’t fall, but really under-performs in both of his races, and now it becomes this thing.

So now you have this guy, first of all, it’s like the… How do you get past that when there’s clearly like this kind of mental block. Well, he starts working with a sports psychologist by the name of Dr. Jim Loehr, and there’s a lot of kind of unpacking to do about everything that had happened, and, you know, we mention, we used the word framing before about, you know, framing what had happened to him to that point, and he had to kind of, first of all, look at what happened the first time when he fell after her sister died and realize that, you know, that was what he needed to do, like there’s a, you know, it’s a really deep story, but like Dr. Jim Loehr and Jansen had decided that at some subconscious level, Dan Jansen had decided that he wasn’t ready to win a gold medal when he was still mourning and that, you know, he almost fell, not on purpose, but you know, he fell, there was a reason why he fell in the way that he did.

And then it ended being a little bit more of a more understandable or relatable episode where when you get into certain events and you put all your focus on the result as opposed to the process, that can be really detrimental. And, you know, it became one of these things where Dan Jansen, you know, whatever, you know, 364 days out of the year focuses on skating his best and his preparation and training and put on the… In the Olympics, he was thinking about, I wanna win a gold medal, I wanna win a gold medal, he’s standing at the starting line, and that’s always thinking about… And that’s a really dangerous and unhealthy way to approach really anything, and the turning point for him was just that… So he had one more chance, the 1994 Olympics, and he decided that I’m gonna… I don’t care about winning a gold medal anymore, he really started to think about, I’m just gonna devote myself to the process of training and skating and enjoying what that journey is, and letting go, and in doing so, in his very last race, he set a world record and he won the gold medal. And so it’s just an amazing story, a ton of different lessons in there and really inspirational.

Brett McKay: Yeah, that lesson, the big takeaway from this is like focusing on process, not results, that idea, it’s very visceral in sports, ’cause there are just so many other stories like Dan Jansen, where yeah, these people who had performed top of their game, but they got started getting focused on the results and then they just crashed, and then they have this reboot period where they’re like, I’m gonna learn how to enjoy the sport, just ’cause I enjoy it.

Sam Weinman: Totally, it’s like, in some ways, it’s very counterintuitive, which is in order for you to achieve the thing you want the most, you have to almost trick yourself into not caring about it too much and find yourself finding something else to focus on. And I’m in the golf world, that’s kind of my profession, and there’s so many stories about guys who are like… Rather than think about making birdie here, I wanna think about just making a really good swing here and just putting a really good stroke on this putt, and that is a far more effective and, you know, constructive way to be than I really wanna win this tournament or, you know, make this birdie.

Brett McKay: Yeah, I mean, that’s when, you’re getting philosophical there, ’cause the Bhagavad Gita of talks about that. It’s like one of the things it says is like, you have the right to the work, but not to the fruits, so you just… You gotta focus on the work and just don’t care about the results.

Sam Weinman: A hundred, and it’s really hard to do, but I guarantee you it’s a far more beneficial way to be, and I would also argue that it also allows you to frame everything that happens as a result of those efforts in a much healthier way, because if you’re focusing on a process and you do fall short, you can say, well, I achieved my goal, ’cause my goal here was to be faithful to the process, to do all the things I could do and could control to be successful. And if I did all those things, I’m not gonna really lament falling short.

Brett McKay: So one of the hardest things about losing, particularly for athletes, I think this is really hard for them, because their whole identity gets tied up in their sport, and this can happen to other people too, in business or work or whatever. But whenever you lose, like as a Greg Norman, like the only thing you do is golf, that’s hard, or worse yet, you lose, you can’t do the thing anymore that you’ve based your whole identity around. And you use Sarah Hess, the soccer player, in her career to highlight what do you do? How do you handle loss where you can’t even do the thing that you love and you’ve spent your whole life building your life around.

Sam Weinman: Yeah, and I did use Sarah as the example, and there are examples everywhere of this, of people having to kinda look at their identity and what they’re associating with and trying to find a way to push forward. And in her case, it was… She was the star soccer player, US Women’s National Team, she’s on that ’99 team that won the women’s World Cup, and then a year later she was on the bench in the Olympics, and she was miserable, and then not long after that, she blew her knee out and had very severe reactions to a knee surgery and basically was really sick, and along the way, her entire identity of being an elite athlete is gone, and she’s this sickly person who’s not playing anymore and not doing what she loves and not feeling good about herself.

And that’s really difficult, whether you’re a professional athlete or if it’s your job or whatever it is, and in her case, it kinda forced her to find, again, like framing, find something to cling to and find another way of building herself back up and feeling good. So there was a couple of things she did. One was, when it was very apparent she wasn’t gonna play soccer anymore, she sought to get her degree in psychology and became a psychologist, and ironically enough, she works with a lot of high-level athletes, and a lot of her work is dealing and helping them deal with the pressures that athletes face and having to frame success and obviously framing when their careers go sideways or go away altogether.

So that was one way that she dealt with it. And the other way she dealt with it was personally. Again, this is someone who had a really serious allergic reaction in a knee surgery and they were afraid she was gonna die and couldn’t walk, and in the middle of this really intense period of rehabilitation, she says, you know what, I’m gonna try to run the New York Marathon, which is like lunacy. They were like, you can’t walk. And she’s saying, no, I’m gonna try to do it. And she would literally walk for five minutes on the West Side Highway in New York until she started crying and then it was five minutes became 10 minutes and 10 minutes became three or four miles, and she ran the New York Marathon through pain, but kind of the use of sheer will and it was just kind of finding something else that she could build toward. And so the lesson of Sarah Hess is obviously persistence, but it’s also about when things are taken from you, you have to find something else to look as your new mountain top, a goal that you can build toward, and she’s a real lesson in that.

Brett McKay: No, I thought that was really good. I think it was interesting, she found it, it was like it wasn’t completely new, it was tangential, like she found something that was related to what she was doing before, but differently.

Sam Weinman: Yeah, completely. Again, the ask is not for you to reinvent yourself completely where you’ve flushed away everything else you’ve experienced to that point, it’s find the elements that you still can use in a new context.

Brett McKay: Yeah, and I’ve noticed… Even for athletes who don’t lose, they had a great career, but their career ends, maybe they’re a collegiate athlete, they’re not gonna go on to the pros, that can be hard because they have to figure out what I’m gonna do now, and the ones that I’ve seen that they thrive and succeed, they find something that allows them to stay connected to the sport but differently, they might become a coach or they become a manager, or they get involved in… I don’t know, something related, but they reinvent themselves, but they build off what they did before.

Sam Weinman: Yeah, and again, I think… We always think about, we always think about athletes in this setting, I think it’s just like these guys who are gods in their teens and 20s and then their careers end, and there’s not the same level of adulation or the same level of positive reinforcement. How do you replicate that? And the answer is you don’t, you have to find satisfaction and positive reinforcement usually from within. Which is… That’s not always an easy thing to do when you’ve been in stadiums full of 80,000 people screaming your name.

Brett McKay: So the one final group you talk about in the book, was this Columbia football team. This is from the ’80s. First off, I didn’t know Columbia had a football team.

Sam Weinman: That’s part of the problem.

Brett McKay: That’s part of the problem. So what was their story? What made these guys unique and what can we learn about losing from them?

Sam Weinman: Yeah, and another great story, and again, kinda dating myself, because this is in the same way that Susan Lucci was sort of synonymous with losing when I was growing up, so was the Columbia football team, because they had lost 45 straight games in the mid-80s in the Ivy League, which is obviously not the highest level of college football, but this is real football, it’s division one 1A, I guess, division 1AA. And there are guys in those programs who literally went to college as freshmen in the fall and graduated as seniors in the spring, and they never won a football game. And… So two questions, right, that occured to me was A, how did you deal in the moment? How did you get through that period when it was incredibly frustrating and humbling and other students are making fun of you and newspapers are mocking you. That’s the first question.

The second question is, how did it shape you afterwards? And I talked to, I don’t know, a dozen of these guys, and a couple of things were very clear. One was none of them said it was easy, all of them said it was incredibly difficult, but they said that, first of all, they all benefited from it in ways that they insist they would not have benefited if they were… Even if they were middle of the road. Like they said, the fact that it was so difficult and so painful made us hungrier once we entered the workforce. It made us really loyal and committed to one another because we had been through this really cathartic experience together, and we’re, our team is closer than other teams because of this shared misery of the experience.

And they’re also like to a man far more persistent and dedicated in their professional and personal lives than probably other teams. Like they say, all of us have been married for 20 years plus, a lot of us have had the same job, like the word they use is sticktoitiveness, they had to develop that skill as a result of having as much disappointment as they did in their football careers. And so I love that story, ’cause I love talking to these guys who are still… They’re older than me, they’re all in their 50s now, all really close, kind of a band of brothers, not to liken what they went through to guys who go to war, ’cause that’s obviously a whole other level. But on some level, there’s this real bonding moment that takes place when you go through something like that together.

Brett McKay: And why do think they’re able to do that? Because I think a lot of people, if they just lost over and over, you’d get jaded. You’d be like the, why bother? I think you had that experience with one of your kids. It’s like they got smoked by this hockey team and they’re just like… The second half is like, why bother to go out? We’re gonna get our butt kicked. So how do you avoid the why bother effect?

Sam Weinman: Well, I think some it’s a testament to the people who stuck around, because it’s worth noting that… I don’t have the numbers in front of me, but if there were 25 guys who started as freshmen that year on that team, only 12 stuck around as seniors. So at some point, guys did drop off, and did enter that why bother phase. And so one would argue that certain guys just have some inherent resilience and they were willing to stick it out more so than others, but it’s also worth noting, I think it’s in the same chapter, I talk about the fact that, this idea that some people are naturally more resilient. Maybe you can start out that way, but resilience is something you can very much develop and foster over time, and for whatever reason, the guys on that group did do that.

And I think at some point, and this probably was true, is that there’s a little bit of wanting to stick it to everyone else by showing them they’re not gonna quit, like all these guys dropped off and you know what? I wanna prove, either to myself, or to others, or to the guys who are still with me, that I wanna see this through. And it’s an incredibly impressive skill. And again, this guy, Nick Leone, who I still keep in touch with, who was one of the “stars of that team,” he says that, “When I went for job interviews, it was actually a real asset, ’cause people were so impressed that I saw this through and I sustained as much as I did in college.”

Brett McKay: So at the beginning of this conversation you said you started this book ’cause you had sons in sports and you wanted… And they had some meltdowns ’cause they lost, and you wanted to teach them about losing. Have you been able to… Has this stuff rubbed off on them or when you try to tell them about the Columbia football team, they just roll their eyes and, “Yeah, yeah, yeah, Dad.” Do you see an effect?

Sam Weinman: I do. So it’s funny ’cause they’re literally lurking in the background while I’m talking right now, ’cause they’re doing this homeschooling thing but, the short answer is yes. They are incredibly sick of hearing me talk about it, ’cause I’ve been talking about it for years. I’m never gonna say that like, “Oh, they’re model losers now because of me.” They still struggle in ways, but I do think… The one thing I say, it’s an important point to make in the book, is being able to accept or embrace losing does not suggest that you’re not competitive. In fact, you probably are more competitive if you’re able to lose well.

And it doesn’t mean that you’re not gonna have these moments of frustration. The difference is that a day later, two days later, you are better equipped to put it in perspective and learn from it. So, the most recent example is my oldest son, who’s again lurking in the background, has become a pretty good golfer. He’s already better than me, and he’s starting to enter some junior tournaments, and he played his first junior tournament, he was 15 years old in a division with 15 to 18-year-olds, so already up against older kids, and it was really difficult. And he… When it was… As soon as it was over, he’s like, “I’m never doing that again. I wanna quit. I can’t play golf.”

All those things that we all go through when we’re incredibly frustrated, and then a day later, two days later, he’s like, “Actually, that experience was kind of fun. I enjoyed parts of it. I wanna do it again. I learned about what I did wrong and what I need to work on as a result of it.” And I’m not at all taking credit for him developing that mindset, but I think he’s more willing to go through that exercise of seeing what the upside would be, maybe as a result of me hammering it as much as I have been over these past few years.

Brett McKay: Alright. Well, hey, Sam, this has been a great conversation. Is there some place people can go to learn more about your work, or what you’re doing now?

Sam Weinman: Yeah, well, I’m the Digital Editorial Director of Golf Digest, so obviously golfdigest.com is my professional home, and obviously plenty of stories of losers there, and it is a topic that I tend to gravitate toward just still even writing about golf, so I’ve definitely written about that. And then I have my own website, samweinman.com, which has more information about the book Win At Losing. I’m on Twitter @SamWeinman, so people can get me there, for sure.

Brett McKay: Alright. Well, Sam Weinman, thanks for your time. It’s been a pleasure.

Sam Weinman: Oh, it’s been my pleasure. Thank you.

Brett McKay: My guest today was Sam Weinman. He’s the author of the book Win at Losing. It’s available at Amazon.com and bookstores everywhere. Check out our show notes at aom.is/winatlosing where you can find links to resources where you can delve deeper into this topic.

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