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Sam Weinman had learned to embrace failing. In an effort to illustrate the benefits of losing to his two young sporty sons, “Win at Losing” was born. As an awards winning sports journalist, he has followed the winners and the copious amount of losers. Sam Weinman looked at inspirational people that have lost big and learned how they transformed their lives for the better like actress Susan Lucci, politician Michael Dukakis and golfer Greg Norman.
Losers to Winners
In a results oriented culture we don’t value the experience of the losers. That is a mistake in that learning to transform experiences of failure into success is worth learning from. Losing can make a person resilient. He illustrates some of his findings with stories of famous moments in athletes recovering from critical losses like Spieth’s shocking collapse at the 2016 Master’s Tournament. It is moment like that, public moments of humiliation and loss that Sam investigates what it takes to rebound.
Sam recognizes a particular formula with people that were able to make this shift in all areas of life. Some of these people never win the gold medal but these VIP’s DID use the experience to look deeply into themselves for the lesson. It is not easy but it is doable and so worth it.
– Hey, Doctor Pedram Shojai, back with The Urban Monk. I am happy to be back in the studio, just got back from some travels. And I love it, I love the travel, I love being away and meeting with people in the industry and talking to smart people, but I also miss my family. So it’s always that’s kind of balance of in and out. And I got to meet with some very interesting kind of entrepreneurs over this last week, at an event called the Bay Bath Water Institute, put on by some good friends. And it’s fascinating to talk to some of these people that are running nine, 10 figure businesses, and talk about some of their foundational moments and they’re all kind of predicated on falling on their face. They’ve had a number of losses, they’ve had a number of challenges and those kind of defining moments have now allowed them to be the people who they are today. One of the guys I spoke with actually, he just went through a divorce and he literally just handed everything over to his ex wife and said I’m gonna start over. Went and lived in his mom’s basement and now he’s worth north of eight figures again because he knows how to do what he does, and it all came from these iterative phases. So, today, we have a gentleman by the name of Sam Weinman on the air in the studio, a book called Win At Losing which is exactly along the lines of what I’m talking about here in really learning how to turn our biggest setbacks into our greatest gains, so welcome to the show.
– Glad to be here, thanks for having me.
– Yeah, this is great, I know that you have run around in some of the golf circles, you were a golf digest and you’ve been looking at this subject matter throughout your career. What can we,
– What can we glean from this? It’s so, we live in such a winner oriented society that no one ever even wants to admit to having lost, right? At least more than once.
– Well I think the most important lesson I’ve learned in this whole process, writing this book is that first of all as results oriented a culture we have, failure and losing is such a valuable step along the way in being successful, I read a book about losing which is not to say that I’m opposed to success, what I am saying is that a very key element to being successful or being happy for that matter is identifying the mistakes you make along the way and whether you can benefit from them or you can learn from them, and beyond that, just finding a way to be at peace sometimes when you make mistakes.
– Yeah, what got you into even looking at this subject matter? I mean, I know that it’s really hard when you get in your head and you really start losing as a golfer,
– You know, to come back, I’m assuming that’s it, but you know?
– No I mean actually, trust me, personally as a golfer there’s, the failures are many and I could talk about it all day but for me it was really two prong, one was as a journalist, someone who’s covered sports my entire professional career and has written about teams and individuals, I found like I was always drawn to the losers more and the sense that I found that the losing locker room was the more honest place, and people were a little bit more vulnerable and probably a little bit more introspective in the wake of defeat, and those were the most interesting stories to me, so that was one part. The other part was, I’m a dad, and I have two boys who are very competitive little athletes, and I found that they were constantly struggling with losing in whatever the context, very often it was athletics, like sports is a big part of my life, so a lot of it started with how they handled losing in sports, and they would struggle with it and I always wanted to impress upon them that losing can be a really valuable experience for them, so, I, you know, there was a couple sort of seminal moments that sort of set me on this path where I said you know what? I wanna prove this point to them and I set out to write a book to do that.
– And along the way, you’re turning lemons into lemonade, I’m assuming there’s some sort of, you know it’s one thing to just feel down and out and say damn it I lost, there’s nothing to take that and make it a transformative experience, so what’s the philosopher’s stone of turning lead to gold here?
– Well, you know, it’s certainly not an easy process, but I would say the people who have done that well are the people who have been extremely honest, excruciatingly honest with themselves and found something in that losing experience that they recognize as a weakness or as an error that needed to be addressed. And my point is that when we lose, those moments are crystallized, like we see our weaknesses so much clearer in the face of failure than we do when we’re successful or even when we’re kind of just floating along, and so, it’s being honest with yourself and being honest with the experience and seeing where those opportunities are that you can address and hopefully take a step or several steps forward.
– So as a dad, you’re talking to your kids about this. Pitch me, okay, dad I just lost this game, I feel so bummed this sucked, what do you got, how is this good for me?
– Well, you know it’s funny because I have been down this road a thousand times with my boys and I’m still going down all the time and first of all, I would say, depending on the age of your kids, they need and we all need that moment of validation that whatever they’re going through is real and the pain they’re feeling is legitimate, and so I don’t think it’s realistic to start right in with the oh you’re gonna learn from this, this is a great opportunity because that’s just not, they’re not gonna buy into that. So you have to kind of allow them that moment of frustration or self pity, whatever it is, and then once some time passes and they’re able to remove some of the emotion out of the equation, it’s helping them sort of perhaps through socratic method, well what, how did that go, what do you think you could have done better? What, you know, what were the areas where you think you fell short? And hopefully along those lines you’re helping to arrive at some answers about, you’re right, this is something that I need to practice or this is something that is gonna help me in the long term. You know, I’ve made the case from the start that it’s not an easy process, but the more you can sort of get them to ask those questions at some point along the way, the more they’re able to eventually come to a satisfying sort of revelation about the process.
– Sounds like there needs to be a bit of an introspective operating system
– That has to be built in and something that is willing to look at the self and constantly work on the self,
– And that’s not really built into our culture too well, you don’t work on yourself, and that’s why you don’t get better.
– Yeah. It’s totally true and now you’re adding the added layer of dealing with kids, so, I think that is a big part of it, which is in every episode there is a part you play, and you have to be open to the idea that you are not perfect or that there was something that you could have done better, and, I think humility is a big part of that equation, because like you said, our culture is the way that we don’t like to show, or consider that we were wrong or that we’re fallible in some way, and so if you can kind of get to that place where it’s just well, you know what, we’re all fallible, we all have our moments where we’re less than our best, and if you can sort of, whether it’s your kids or just anyone, buy in to that first premise, then you can get to some of these difficult areas in helping you sort of uncover some important truths.
– Yeah it’s tough, I’ve seen this actually at my kid’s school already, you can just tell what a kid’s mom or dad is like just by interfacing with them, where it’s like wow, you probably have a dickhead dad, you know, like an ego driven dude because the way you’re already seeing the kid doing this thing, and it’s like wow okay, he’s teaching this kind of ego oriented interpersonal interface early on and that’s the guy that gets hurt, that’s the one that really can’t stand losing in a lot of ways.
– Right. Yeah, I mean there’s certainly, kids certainly take a lot of cues from their parents, and you know, I think one of the things that we struggle with is that when parents are unwilling to accept that their kid was wrong in a situation, you know, whenever there’s a, whatever, for an altercation at school, and there’s two kids involved, and once in a while you gotta deal with that parent when like the parent is unwilling to see that their kid was at all wrong, that’s a recipe for trouble, because now you’re operating on this premise that your kid can’t do anything wrong, and that’s the worst message you can send, and so, I’ve certainly dealt with that personally and I certainly deal with it like in talking about people who struggle with losing, the people who struggle with losing the most are the people who are unwilling to look at themselves in a critical and constructive way.
– Yeah, yeah, I mean we could go down the rabbit hole of just kind of unpacking what that means psychologically, because, you know,
– Building this whole thing on a house of cards, but, it’s really a question of resilience, right? Psychological resilience, interpersonal resilience, and so if you can have the resilience as a kid to understand that sometimes you win, sometimes you lose,
– That gives you a lot more breadth in your personality to not just feel like you got slammed every time you lost a basketball game, how do you teach that?
– Like what can I learn as a dad to teach my kids?
– Yeah. Well a lot of what I have learned about this topic comes from other people, and certainly one of the influential people was someone named Carol Duac who has written and talked about something called a growth mindset and a fixed mindset, and at it’s most basic level, you want your kids to have a growth mindset, we want ourselves to have a growth mindset which is that we are not defined by, you know, this achievement or this episode or our talents, but we are defined by our approach to process and our approach to how we handle challenges. And so one of the things you want to teach with your kids is that if they are good at something or bad at something, that can be improved upon, that you can get better at something, that you can grow from whatever experience and when you have failures, whether it’s in school or in sports that those are things that you can embrace as opportunities to grow. So the classic example that she gave was, you know, she gave a test, and stop me if you’ve heard this before, she gave a test to a group of fifth graders, and half of the kids after the test, it was a really easy test, half of the kids after the test, she told them, wow you’re really smart, you know it’s obvious from this test that you are really smart, and then the other half she said wow you worked really hard on that, it’s apparent that you really applied yourself in trying to solve the answers to these problems, and then the interesting thing is in the subsequent test, the kids who were told they were smart, when they were given a more difficult test, they couldn’t handle it well, because they were like well I’m smart, how come I don’t get this? This is ridiculous, I’m supposed to be smart and I don’t get it, whereas the kids who were told wow you worked really hard at this, when they were given the more difficult test, they embraced that and they said okay I’m ready to take on something more difficult because I work really hard and I can work hard at this as well. So it’s that mentality that we want to apply to our kid which is, embrace the challenge or embrace the effort that is required here and not look at all these benchmarks as a reflection on your self worth.
– Yeah, that’s amazing, and that cultural thing right there makes a world of difference, right?
– For me, I said this 1000 times on this show, that translation of kung fu is hard work, and so if you have an operating system that is basically oriented in kung fu, you’re never worried about hard work, you always know that you’re going to try hard and try harder, but that’s the game of life.
– If you’ve been told that you’re smart, forget about it, right?
– Yeah, that’s, you know, that’s important work and I think any parent listening to this needs to just kind of really just get that iterated into everything that you’re doing in getting your kids to understand that this is a process and frankly, next week’s homework is always gonna be harder.
– That’s how this side of the world works.
– Yeah, so,
– And the other thing about it is, a lot of this is talking about how we handle failure and disappointment, but it’s really just as important if not more important in how we deal with success which is, when you’re a kid, has the most success in fourth grade or sixth grade or whatever, it’s important for you to be not like wow you’re really smart and wow it’s clear that this is gonna be easy for you, it’s wow, you know, you’re developing the right habits to be successful in school, you’re working hard, you’re learning to study, all those things, because like you said with kung fu, the real gift is not that you have some magic ability to do stuff, it’s that you have learned the value of effort and diligence.
– Yep, yep, and as a kid, it’s priceless, I know, look, we all grew up in different times and we didn’t know this stuff, and so you know, we’re all dealing with the fallout of that. And so, say now you’re like a 50 year old person and you got fired from your job, right, and it’s devastating. How does one take the same type of orientation and really shift it in mindset?
– Sure, I mean it’s conceivably something that we’re talking about that’s applicable to any age, but if you’re 50 years old and you’ve lost your job, there’s two ways to look at it, first of all, I’d be remiss and not talking about the fact that there are occasions when things happen that are outside of your control, when you lose a job, you might have lost your job because of factors outside of your control, and when you have that moment of honesty and you’ve really asked all the hard questions of yourself, and you can honestly say well you know what? It just, I was downsized, I lost it, well there’s some taken from that, but, let’s say there is something that you did wrong, let’s say it was a failure made along the way which it’s the same thing, it’s asking yourself those difficult questions like wow, did I rub my coworkers the wrong way? Was I unprepared in ways that I, that really were detrimental and I need to be more prepared next time? Is my skill set lagging behind? Do I need to develop a new skill set? Like again these episodes we have when we lose or fail are real crystallizing moments and so I would look at that episode as painful as it is, as an opportunity to see very clearly the areas that you can improve.
– You mentioned a number of famous people in the book who have been rolling like this historically for a while, I think of the old kind of KFC recipe and the amount of times that got banged on the door, but from Thomas Edison to Abraham Lincoln, give me some examples of these household names of people who we think of as such heroes, who definitely went through these throws.
– Sure, I mean, when I wrote this book I set out to just talk to people whose episode or failure resonated with me and it’s a kind of a wide gamut, so, an example again, I come from the sports world, I’m in the golf world so I, Greg Norman is a golfer who is very well known for having a lead in major chain shifts and blowing those leads, and not winning, and the most famous episode was the 1996 masters where he had a six out lead going into Sunday, everyone thought he was finally gonna break through in this important tournament and he fell flat on his face on Sunday, he shot 76 and lost by 5 and it was just sort of a humiliating moment. And the great moment from that was that Norman was a larger than life figure in a lot of ways and kind of had this presence about him, was very successful even amidst these losses, had won millions of dollars, and it was very human moment, he owned up to mistakes he made, he recognized that it was a very painful thing, he gave the credit to the guy who won, afterwards when he’s in a press conference after the tournament was over, he talked about how he screwed up and that it was all on him. And in a very small way but in a very symbolic way it was an episode of a guy who become very human to a lot of people because for a lot of times people couldn’t relate to Greg Norman, he was a vastly successful golfer, but here was a guy who was admitting that he screwed up, that it hurt like hell, that he was fallible in ways that he probably wasn’t willing to admit before, and I always made the case that he won more fans in losing that tournament than he did in winning 90 tournaments around the world, and it’s true, there’s a ridiculous number of letters that he still receives, I think he’s gotten, he’s received like 10,000 letters from people that he received after losing that tournament, so, that’s an example, and I talked to people, and, one of my favorite chapters in the book is about, it’s another sports example, the book’s not all sports but there is another sports example which is the Columbian University Football Team in the 1980s was renowned because they lost 44 straight games while they were in college, so is a group of guys who went to school as freshmen and graduated as seniors and never won a single college football game, so your reaction to that is naturally, wow, what a horrible experience, what a waste of time to go to college and only lose, and every guy on that team that stuck it out, there were like 12 guys who went from freshmen to senior, didn’t win a game, say it was the most important experience and the most valuable experience of their lives because it sort of taught them real resilience, and it gave them a kind of a hunger that other guys did not have, and when they emerged from college, they all said, first of all, they were very close to one another because they went through this difficult experience together, but also they had something to prove, they had this sort of chip on their shoulder, and it led to almost all of them to a man being extremely successful not in football but in business, in law, in medicine, and it’s like a real seminal moment for them.
– Interesting, you know the ginseng roots are very valuable, you go to China, Hong Kong, stuff like that, you can get a ginseng root for 2 to 300,000 dollars and business men go crazy trying to get this stuff. And what determines the value is really the struggle and the strife that that root had to endure in order to grow and so the actual active ingredient of the ginsenicide, concentration of that is increased with the more strife that this root went through, and that’s, you know, in correlation to the amount of money paid for it. And so again it’s that same principle of working hard, I mean these guys, I wonder if there’s been a followup story a couple decades later and all this, just keep following these guys, who, you know,
– Developed the grit.
– Yeah, and that’s what it is, it’s kind of an early exposure to the fact that life’s hard and that you’re gonna kind of fall flat on your face and you have to persist now granted, it’s college football, it’s not the end of the world, but in their world where all their classmates were kind of at any Ivy League school and kind of were known to be very successful, these guys were kind of the laughing stock of the school, and so it was a very important experience for them and an early recognition that these painful moments can be really great enlightening experiences.
– Yeah, I wonder if they made a documentary on that story, that’s actually really interesting.
– Yeah, that’s fascinating. So we have people throughout the course of time, you mentioned the founder of GoPro, what happened there?
– Well he was, Nick Woodman was a guy who, he’s from the Silicon Valley culture, had started a company, I think maybe a couple companies, and it fell flat on his, you know, it fell flat and it was a complete bust, and he moved back in with his parents after it was over, he ran out of money, and he decided to make a sort of career pivot where he was just gonna go around the world and go surfing and kind of find himself. Well on the way when he was surfing, he decided he wanted to sort of, you know, video while he was surfing, and so he kind of jerry rigged this idea for a camera that he made that he could sort of video himself surfing, and from that experience came the earliest version of the GoPro camera which is now worth billions of dollars and very successful, so, it’s a great sort of metaphor or example of how from his worst experience which is the failure of his business came the genesis of this new idea which made him ridiculously successful.
– It’s part of that kind of Silicon Valley lean start up mentality too, which is, you know, iterate, fail fast, move on, right?
– And it’s become part of the culture, it’s become really interesting that this is what big money embraces, this is what smart people understand, I mean look it’s not that you’re not gonna fail, learn from your failure because it’s a lesson,
– And then move forward.
– Yeah, and what’s really interesting about Silicon Valley is that so many things about that culture are contrary to what we’re taught because one of the sort of important lessons they teach out there is to know when to move on, like know when to kind of pull up stakes and give up on your idea, which is sort of contrary to what we’re taught as kids which is like be persistent, see your idea through, don’t give up, and part of what they say is actually it’s a really important skill to know when something is not working, it takes bravery to know this is not working, I’m gonna, that’s a very difficult thing to do, but it’s this idea that in order to know what can work, you need to first know what doesn’t work, and that’s something that they in Silicon Valley have really got down to a science.
– So there’s this whole other class of people that this should apply to but it’s so damn tough, right? And say, I went to med school, this dude went to law school so you kind of push all your chips in and then you become this professional person with this title, and frankly, probably 100, $200,000 of student debt and identity and all this stuff, and then you know, five years into it, you’re like oh shit, I don’t like this life at all, right?
– How do you get iterative there, like how does one become transformative once you’re kind of a little further entrenched? And all the excuses are there frankly, right? You have so many more excuses to say well I gotta stick now.
– Yeah, well, it’s a very good point I mean, I guess I would go back to two things, one is this whole growth mindset, which is that even if you’re six years out of college, seven years out of college, however further along your career, we are always growing, we are always learning, and so if you look at life as sort of an endless process of trying to get better, then you can get used to the idea that this early experience that you went through that it was an opportunity to, again, learn what you didn’t like or learn what was not for you, you hear all these stories about people who go through career changes and they are grateful that they had the first experience because they learned, you know what, that wasn’t for me, I went to law school, I went out to be a lawyer and I’m so glad that I went through that because now I know that I definitely don’t want to be a lawyer. It’s an expensive path to take,
– But those are the people who have a much clearer picture of what they want in life because of something they went through in which they learned they didn’t want to do it.
– Yep, yeah, and just rolling with that same example, this was a friend the other day, they were a high powered lawyer and they just wanna leave law and go do massage or something and help the world, I said well what do you care about? He said the environment. I’m like well why not take the skillset that you have and help Earth justice or help the Green Peace people, and use the kung fu that you know somewhere where you can apply it and you’re passionate, right? And it was just like it’s all or nothing, like I’d just jump off this ship and not be a lawyer,
– Just because the eight people in your law firm piss you off, so there’s a lot of that, too, right? It’s just stepping back and thinking about things a little more objectively and pivoting instead of just dropping everything I would assume.
– Of course, I mean pivoting like you said, it can be dramatic, it can be, I’m gonna go from being a lawyer to being a physical trainer, or it can be, I’m gonna be a corporate lawyer and I’m gonna be a non profit lawyer, like there’s obviously small pivots along the way, the key is to kind of identify the part that is really objectionable to you. This is the part that I definitely don’t like and I’d like to get away from that, and you know, if you can do that, you know that part, then there’s a lot of wiggle room in between.
– Yeah, yeah, and that’s the thing is under duress, we don’t see the wiggle room and that’s a direct correlation with the resilience argument, right? Like the more resilience you have the more you can kind of look at something without completely collapsing and being I’m such a loser, right?
– Yeah, totally, this actually goes back to the idea, talking about with my kids which is like we all need that moment where we’re sort of separating emotion from the equation or, like you said, I hate law, I’m never gonna be a lawyer again, there’s probably a lot of emotion in that and there’s probably a lot of, you’re kind of clouded by an immediate experience and part of what we’re talking about is, first of all if you go through enough of these episodes, you realize it’s not the end of the world when something doesn’t work out, there is always a next path and if you’re able to kind of allow yourself the time to eventually look at things really objectively and clear eyed, then you’re not gonna make that extremely dramatic move, it might be something just a little a little subtler.
– Yep. There’s this one thing that I hear a lot and it’s a big challenge in the community is rejection, right? And so, you know, everything’s going fine, you think your life is cool and all of a sudden your significant other is like later, I don’t know you, right? And then whether it’s a work relationship or personal relationship, that rejection I found people really getting hung up on, so what wisdom do you have there in turning that to lemonade?
– Yeah, well first of all I would make a very strong case that that’s a universal thing, if we go back to the idea of, sometimes it’s not always your fault, especially when we’re talking about a personal relationship, in the same way we talk about employee who was downsized for reasons outside of his control, there might be another party here who has changed or moved into a direction that is not really a reflection of you or who you are, or your self worth, so that’s the first part, the second part is, you know, as with anything else, when you go through an end of relationship or some sort of rejection, it’s as good an opportunity as ever to again look at yourself and look at your role, like was I as attentative as I could be, was I a good listener? Am I too self centric to be in a relationship? Like these are all very difficult questions that come to the floor when these things happen, and again, as difficult as they are, these are the real catalysts for positive change because it’s sort of, you’re forced to deal with it, and so again, I’d go back to the idea, like, you’re not gonna see it right away when the person you love walks out the door, you’re not gonna be so grateful for the opportunity, but if you allow yourself the time to really look at it objectively, you might get to that realization.
– Yeah, and that’s the hardest part, you wanna blame them, obviously, you’re the victim, but you know, it’s probably been festering for a while, no body I know is an angel, you know what I mean? And so it’s always dirty
– Right of course.
– On this side as well, and so, but then developing that culture, there’s so many people that wanna externalize that pain, it’s almost like going through the steps of grief
– Where at first you’re pissed and you’re like that jerk, I can’t believe they did that, but once you start getting into that level of introspection, any wisdom on how to really just stop playing the blame game and asking oneself what is it that I may have done wrong?
– Yeah, I mean, I don’t know if I have wisdom as much as I would say that blaming really doesn’t get you anywhere. I think we’ve seen it, you know, American culture right now, politics and everything else, it doesn’t arrive at constructive solution so it might make you feel better but it’s not gonna get you to a better place or a higher place, it’s just gonna basically prolong the problem, and so again, I don’t know if that’s wisdom as much as like, when you have the temptation to blame others for your problems and your lot in life, make sure you’re aware that that is only gonna get you so far and that’s not very far at all.
– Yeah, exactly, exactly, and where it gets you internally is an ulcer, you know, it’s like it cooks you
– Inside out.
– And look, we’re all guilty of it, myself included, it’s very easy at the moment to say that all the problems that arise was of something that are outside of you. But I think, again, give yourself the time and perspective and you’ll realize that’s not necessarily the case.
– I love it, I love it. The book is called Win At Losing by Sam Weinman, “How our biggest setbacks and lead to our greatest gains”. The book is already out, and man, I really enjoyed this conversation, smart guy and look, here’s the thing, you’ve been around people, there’s only one guy that really wins the golf tournament, so everyone else has some degree of kind of introspection that goes along with saying well yeah that didn’t turn out the way I hoped, right?
– And that’s the experience, that’s what sports are, that’s what life is.
– Yeah that’s why, I mean look, my background is sports but I also feel like sports are great examples of that whole idea that, you know, when there’s a loss it is a perfect opportunity to look at what can be better, and so, but that’s, it’s applicable well beyond the athletic realm as well.
– Yeah, yeah, well it is life, the old metaphor sports is life, right?
– Yeah. It really is, life is sport. So listen, I wish you the best, I love this work, keep up the good work and for my audience out there, where can you turn this around and really look at getting out of the blame game, finding those losses, metabolizing those losses and turning them into the nuggets, right? Like how do you take the coal, turn it into a diamond? And all chemical translation as turning lead to gold, this is what we do everyday, right?
– There’s a metaphor for life, how do you find that in your own life? Let us know in the chat threads here and keep up the good work at digging in your own life and Sam, thank you so much for being here.
– Well it’s my pleasure, thank you.
– Thank you.