Passion Struck with John R. Miles - Poker Legend Annie Duke on How You Get Good at Quitting EP 255

Episode Date: February 16, 2023

Annie Duke, who gained expertise in quitting from her successful career as a professional poker player on the world stage, advocates for quitting things more frequently. In our interview, she delves into the science of quitting and teaches us how to overcome our obstacles and develop the ability to quit when it's necessary. We discuss her latest book: Quit: The Power of Knowing When to Walk Away. Annie Duke and I Explore How You Get Good at Quitting In our interview, Annie Duke imparts the skills necessary to become proficient at quitting. She cites examples from the experiences of accomplished individuals such as elite athletes like Mohammed Ali, leaders of major companies like Stewart Butterfield, the CEO of Slack, and successful entertainers like Dave Chappelle. Duke argues that quitting is crucial to success and offers techniques for deciding when to persevere and when to abandon a pursuit to save time, energy, and money. Full show notes and resources can be found here: https://passionstruck.com/annie-duke-on-how-you-get-good-at-quitting/  Brought to you by ZocDoc, Shopify, and Fabric. --► For information about advertisers and promo codes, go to: https://passionstruck.com/deals/  Like this show? Please leave us a review here -- even one sentence helps! Consider including your Twitter or Instagram handle so we can thank you personally! --► Prefer to watch this interview: https://youtu.be/Qf9s9OypF-s --► Subscribe to Our YouTube Channel Here: https://www.youtube.com/c/JohnRMiles Want to find your purpose in life? I provide my six simple steps to achieving it - passionstruck.com/5-simple-steps-to-find-your-passion-in-life/ Want to hear my best interviews from 2022? Check out episode 233 on intentional greatness and episode 234 on intentional behavior change. ===== FOLLOW ON THE SOCIALS ===== * Instagram: https://www.instagram.com/passion_struck_podcast * Facebook: https://www.facebook.com/johnrmiles.c0m  Learn more about John: https://johnrmiles.com/ 

Coming up next on the Passion Struck Podcast. The problem is that waste is not a backward looking problem. It's a forward looking one. So what you would poker players, what you would entrepreneurs, what you see honestly with people climbing Everest, with people running projects that are over budget and over the timeline, continuing to develop products that can't find product market fit,

staying in relationships too long, staying in jobs too long, whatever it is, that what you'll hear from them a lot is, but if I quit now, I'll have wasted everything that I've already put in. Welcome to PassionStruct. Hi, I'm your host, John Armiles, and on the show, we decipher the secrets,

tips, and guidance of the world's most inspiring people and turn their wisdom into practical advice for you and those around you. Our mission is to help you unlock the power of intentionality so that you can become the best version of yourself. If you're new to the show, I offer advice and answer listener questions on Fridays. We have long form interviews the rest of the week with guest-ranging from astronauts to authors, CEOs, creators, innovators, scientists, military leaders, visionaries, and athletes.

Now, let's go out there and become PassionStruck. Hello everyone and welcome back to episode 255 of PassionStruck. Recently ranked by FeedSpot was one of the top 50 most inspirational podcasts of 2022. And thank you to each and every one of you who come back weekly to listen and learn how to live better, be better, and impact the world. If you're new to the show, thank you so much for being here, where you simply wanna introduce this

to a friend or family member. We now have episodes starder packs, which are collections, or fans favorite episodes, which we organize in the convenient topics to give any new listener a great way to get a clinic everything we do here on the show. Either go to Spotify or passionstruck.com slash starter packs to get started. And in case you missed it, earlier in the week I interviewed Matt Higgins,

who is the co-founder and CEO of the Private Investment firm RSC Ventures. An executive fellow at the Harvard Business School where he teaches, the course Moving Beyond DTC, a guest shark on ABC Shark Tank, seasons 10 and 11. He will soon star in his own spin-off business hunters, also executive produced by Mark Burnett. Matt is the author of the brand new book, Burn the Boats, Cos Plan B Overboard, and unleash your full potential. Please check it out in case you missed it, and I also wanted to say thank you so much for your support of the show, and if you love today's episode or the one I mentioned

with Matt, please consider giving us a five-star rating and review. They go such a long way from improving the popularity of the show and bringing more people into the passion structure community where we can enlighten them with weekly doses of inspiration, hope, connection, and meaning. Now let's talk about today's episode, which tackles the science of quitting. Often, we find ourselves stuck in a job, relationship, hobby, or pursuing a goal for far too long. Knowing what you know now would you still make the same decision? Did you experience concerns about embarrassment, how it is, and not leaving in impression

or legacy, that kept you from moving toward more promising opportunities? The fact is not quitting can be detrimental, as shown in the example of Olympian skier Lindsay Vaughn, who incurred unrecoverable injuries before finally deciding to retire from skiing. Ultimately, the sacrifices that she was bearing became too high. What if our long-held beliefs and diligent efforts aren't enough when new information surfaces? What if you were making false progress? Have you ever thought about enlisting a quitting coach? These are all topics that I will discuss today with our guest, Annie Duke, who is an author,

corporate speaker, and consultant in the decision-making space, as well as a special partner focused on decision science at first round, capital ventures, a seed stage venture fund. We will explore Annie's latest book, Quit, The Power of Knowing When to Walk Away, which was released in October 2022. We also touch on her previous book, Thinking in Betts, which is a national bestseller. Annie is a former professional poker player, where she has one more than 4 million in tournament poker. During her career, Annie won a World Series of Poker bracelet, and is the only woman to have won the world poker tournament of champions and the NBC national poker heads up championship.

Thank you for choosing passion struck and choosing me to be your host and guide on your journey to creating an intentional life. Now let that journey begin. I am absolutely thrilled today to welcome Annie Duke, the Passion Start podcast. Welcome. Hi, thank you for having me, John. Well, it's such an honor to have you, and as we discussed before the podcast, you were recommended to me by one of my favorite people, Katie Melkman.

One of my also. Yes, so very honored to have you here today, And your book, Quit, is just amazing and has gotten tons of incredible reviews. So, we're going to dive into that throughout today's podcast. But before we do, I wanted to ask you this question that I'd like to ask to set up interviews. We all have moments that define us. Was there a moment or moments as you were growing up that have led you to where you are today? I think there's two pieces to the puzzle. I've spent my whole life thinking about decision making under uncertainty. I think the people think that I've actually done a lot of different things, but it's all really kind of the same thing, whether it was the cognitive science work or poker, consulting, exploring, through writing these books. It's all a round decision making under uncertainty. And I sometimes wonder like, why am I so obsessed with that topic? Because I've really been obsessed with it since I was 21.

And I think part of the reason is that I actually grew up in a household where there was a lot of uncertainty. So my mother was a pretty severe alcoholic, and that just creates like for a kid growing up, it's like things are very unpredictable in that kind of environment. So I think that was something that I was trying to navigate when I was a child, like as I kind of think back on that, and that seems to have carried through in this particular way where first of all I think I've been ease with this uncertainty because I lived it and it's just something I think about a lot like as things become more unpredictable as there's more luck involved as you're not sure what's coming next what does that look like for you but then I think separate from that I've also thought, so this kind of now I'm going to go on the bad side is I'm clearly someone who feels the need to produce. Like and I don't

think necessarily in a healthy way and I think that also is coming from this contrast between what was going on my mom was going on my dad. So my dad is an incredibly productive human being He was a teacher. He prided himself. I never missing a day of work. He's written I'm gonna get the number wrong, but somewhere close to 50 books himself Yeah, he's someone who's just really a workaholic and a very deep way. And so I think, separate apart from obviously, my dad is wonderful and he totally loves me

and all of those things. I think I heard the message loud and clear that the good parent is the one who works. So I've actually been last spring, I put some sort of intention to what does it feel like not to be producing, at least producing in the sense of producing in a public-facing way. So after I finished the draft of Quit,

there was still stuff I had to do, like a variety of edits and things like that. I told my clients, goodbye for two and a half months or so, and I just was like playing a lot of tennis and walking my dog a lot. Right? And so that was hard, but it actually felt really good. And so that's actually something like I'm really working on right now, is there's different ways to be productive. And I'm trying to really work on like this way of being productive, which is just like walking my dog is a very productive activity. So that's kind of what I'm working on right now. But I think that that sort of comes from this weird childhood that I had. Well, I'm glad you brought up those two activities because

they're two of my favorites and actually Katie Melkman's a kind of split-ers girl. I have a broken wrist right now from tennis. I've been out for three weeks. It's killing me. It's killing me. But Katie, I am not in Katie's lead. Obviously Katie was possibly thinking about going pro. So I have nowhere near Katie, Milfin level, but I do love the game. Well, I have a black lab, and I welcome about five miles a day,

and it's when I do a lot of the research for podcast and listen to upcoming episodes of casts if they've done podcasts before. So I mean, it's well-used time. So I'm really interested in that. I was walking my dog. I wouldn't bring my phone with me. For just the reason that I was like, no, like walking my dog is the activity. So that's what I was working on because I think that I actually do need to work on that. Well, it ironic that you bring that up because I am preparing to do the 12 hour walk and I'm not sure if you're familiar with about this, but I'd call on a radio on the podcast a few months ago and he has

a brand new book on this and you basically walk for 12 hours, but as you said, I can't even bring the dog nor can you turn on your device. So it's really an introspective way, as you're saying, to quiet the mind and spend the full day with yourself. Yeah. Yeah. So I was getting about three hours a day, but I had my dog with me. Well, many of the listeners recognize your name because you are a very well-known former professional poker player. And I wanted to ask you, what is the most important strategy that you learned

that differentiates an average player from a professional? Yeah, so I think this is interesting, because I think that if you asked most people, they would say something like, oh, they're really aggressive, or they can really get a dead read on somebody or something like that. But I think actually when you just look statistically, the biggest differentiator between really great players and amateurs is quitting. So poker has this ability to quit, which is called folding.

So quitting is not even just loss cutting, but loss cutting would go under-quitting. So folding is just cutting your losses. It's just getting out of the hand. And when you look at professionals versus amateurs, there's all sorts of different ways where you can see that professionals are quitting more. I think it would be surprising to people.

They fold way more hands so that they can concentrate their capital on the ones that are really worthwhile, right? So they're trying to get rid of hands early when they figure out that they're not worth continuing with. So in a game like a Texas Hold-Em, where you get to dealt two cards to start face down, obviously. Amateur is going to play over 50% of those two card combinations in a full game. And a pro is only going to play between about 15 and 25% of those hands. So it's just like a lot more folding. So that means that a pro is folding like 75 to 85% of the time. Just like literally right off the bat, just look at the first two cards I'm done.

Then when you actually start to get into a hand, right? So you now started to invest money in the hand. Again, pros are just better at folding when they can kind of see that their hand is not the best hand. It doesn't have a high enough probability of winning or that sort of under that category of a high enough probability of winning that either the cards on their, the hand on its own isn't good enough to stand up, or there's not a higher problem, high enough probability that I could bluff you in order to win. So those would be the two ways that you could win.

And when you figure out that your expected value has gone negative, in other words, for every dollar you put in, you're going to get less than a dollar back, right? That you want to be folding in those situations. And pros are just much better at doing that. And what I think is kind of interesting on sort of both fronts is that when you can actually hear the chatter at the table, so this is one thing that makes poker so amazing is that we can study cognitive bias, right? We can read Katie Milkman's book and see what bias is. We can read Daniel Conneman, thank you, Pais and Flow and go, oh, these biases are very interesting. But then when you sit down at a poker table, you'll hear people say them out loud,

which I think is like so amazing. So one of the things that players will say is any two cards can win. Okay, so what they mean by that is, look, it doesn't matter whether you have two aces or a seven and a two, once those five cards come down in the middle, doesn't matter what you have, you could possibly win the hand. Okay, so when we think about fear of regret, like regret a version,

what's happening is that they continue playing because the regret that they'll feel having folded a hand if the cards in the middle come out favorable to that hand. And so now they're not sort of raking in a pot that they otherwise would have, is so painful that they'll basically play a hand and until they have a lot of information that the hand isn't going to win. The problem is by then you're already dead, right?

Like that's not the point that you're supposed to fold. You're supposed to fold when, and this is how a pro would say it, any two cards can win, but not enough of the time to make them profitable. So you're supposed to fold at the point that the hand is not profitable for you to put. That does not mean that you're going to be sure. And what it means for pros or amateurs is that you're going to fold lots of hands that it turns out we're going to win. Like I can take the worst hand in the deck, which is a seven and a two, and you know what, when those five cards come, maybe I would have made a full house, and I would have won the day. But I'm not going to do that enough of the time to make it profitable

to put my first dollar in with that hand under most circumstances, unless I'm specifically bluffing. So I'm not saying I've never played a 7 and a 2, but it's under very narrow circumstances. When I feel I have a very good opportunity to bluff my opponent, then I might play a 7 and a 2. But I know that I'm bluffing. I know I'm not trying to actually win the hand by making it, right?

All right, so you can hear that whereas poker players are like, whatever, right? Like, all right, the cards came out of what a one, who cares? That's what professionals are doing. They don't care. So that's kind of like the first piece where you can see this, like, this what if problem? Like, but what if my hand would have won?

And then if I have to see it, I'm going to be so sad. Then the other thing that I think is so interesting is this sunk cost problem, right? So once people are sort of in the middle of the hand and they've got lots of money in the pot, you'll hear them say, I couldn't fold because I had too much money in the pot already. Okay, so they'll say this out loud.

I couldn't fold because I had too much money in the pot or they'll say, I had to protect my chips. So that's the same thing, right? Like I had chips in the pot. I needed to protect them by continuing to play But again No, the money that's in the pot is already in the pot That is not your money

That is the pots money at that point and all that matters is do you have a high enough probability from here forward? To make it worthwhile to continue to play? So one way to think about it is like if you parachute at me in, so I have no money invested, if you parachute at me in and said do you want to take this hand right now? Would I say yes? That's the question, right? And if my answer is not in a million years, then I shouldn't play. It doesn't matter that I already put money in the pot. So if we were to think about that mathematically,

if I have a hand that I think is only going to win 10% of the time, and there's 200 in the pot, and I have to bet 100 in order to try to keep playing, I'm only getting two to one. So what that means is that to keep playing, I would have to believe my break even point as a belief that I would win 33% of the time. But I believe I'm only going to win 10% of the time. So therefore, I must fold. So if that's the case, it doesn't matter that part of that 200 that's in the pot came from you. It's literally irrelevant to the decision, but what you can hear from Amateurs is that it's very relevant to their decision.

It matters a lot to them that they have money in the pot and that if they fold, that money is going to be gone forever. They're not going to be able to get it back and it causes them to stick in situation where pros are like, meh, whatever, I don't want to play. Because pros recognize that it's not about what happens on this hand. It's like you're playing one long game. And it's about maximizing your return on investment over time, making sure your chips are going in the pot in situations that are favorable to you and that you're exiting situations that aren't favorable to you and that's really what they care about. So that's where you can see like the humongous difference between the two groups. I think that's the most defining characteristic of great players is this ability to not succumb to those cognitive biases that would cause you to stay in hands. Well, I think it's a great lesson as well for entrepreneurs or people starting their own business who might be listening in today because I have an example of this. I have a friend of mine who has had this start up for at this point, I think he's going on a decade, and I was on the board for five

or six years. Oh, so you quit. And he continued to take millions and millions of dollars from investors, yet he has never once driven a profit. And I told him when I was on the board five years ago that he should shut down the company. He's taking money, but I told him it's not the honorable thing to take money if it's not going to achieve the results that you're promising. But it's one of these things where I think he and many

investors have so much some cost and what they're doing that they can't fathom to get out of it. I think it's a trap that a lot of people get into. Yeah, so we have we have the intuition I think is individuals that when we get signals from the world that we have to quit that we will do climbing Mount Everest in the snowstorm hits you like obviously you're going to turn around right like we all have that intuition. It's that look at all the people who continue to climb up Mount Everest when there's a snowstorm do you think they're really different than you are? They're not. So it turns out that we actually escalate our commitment to the cause. That Katie Milpin has done some very good work on this problem, by the way. So it's like, we think we're going to turn around, but we actually escalate our commitment to the cause.

Like our intuition is actually the opposite of what we actually do. So there's so much evidence that shows that intuition is just wrong, that we actually do the opposite. So, the question is like, what's making us do that? And so, one of the things is what you said some cost, right? Like the time and effort and money and attention that you have put into something where if you quit sort of a goal, you feel like you've abandoned that somehow you've wasted that time.

The problem is that waste is not a backward looking problem. It's a forward looking one. What you see honestly with people climbing Everest, people running projects that are over budget and over the timeline, continuing to develop products that can't find product market fit, staying in relationships too long, staying in jobs too long, whatever it is.

What you'll hear from them is, but if I quit now, I'll have wasted everything that I've already put in. And I'm sure that your friend feels that. Like, I've come so far. I've put so much time into it, so much effort, my heart and soul, like all these things. And they're thinking about waste as a problem that's retro-spective,

but it's not. Waste is a prospective problem. It's a forward-looking problem. Once you realize that the cause is lost or at least doesn't have a high enough probability of succeeding, putting any more time and effort to it into the future is where the waste lives. So we sort of create actual waste

by continuing with things that we ought not to be continuing with because we're worried about wasting what we had in the past or what we've put in the past. And then what happens is like your friend like five years ago, I could have shut the company down. So now where are we? Five years later, it's still not going well. I'm sure your friend is brilliant. It sounds like very gritty, very dedicated, hard working, determined. What could he have accomplished in those five years if he had quit and started doing something else? Maybe he could have actually changed the world, right? Like, maybe he could have actually created an amazing business, but

in service of protecting what you've already put in, he now has actually wasted five years. Right? So because it's past the point at which you should have, in which maybe he could have accomplished great things. And I think that's the real tragedy of our inability to walk away from things that aren't working. Well, one of the questions I was going to ask you is what can playing poker teach you about life. And I think you just answered that through all those different examples. So I have one more question on poker that came from the audience, but I'm going to phrase it like this. I am fortunate enough to know a number of former professional athletes, and the majority,

I know, especially those who played in the NFL, don't even go to football games or even watch it anymore. And so there's this good and bad that comes with being a professional athlete. And the question that I have for you is what are the best and worst things about being on the poker tour? Well, I so actually interestingly so I retired from poker in 2012. I neither play it nor watch it. In a decade, I can count on one hand a number of times I play poker and most of my fingers are used for a charity event. And then I think I need one or two fingers for playing in my basement low stakes guts, which I don't even know if you would call that poker. So I don't play it or watch it either. What are the best things and worst things about being on the tour? I mean, the worst thing, and like you have to travel a lot, I had kids.

So I actually only went to tournaments where I knew that we're going to be televised because I didn't want to travel and be away from my children very much. But I think that for other people who do a lot of traveling, I think it's hard not to have a home base. Even if you're 25 and you don't have kids and I think that's just hard not to have, this is where I live. So I think that's really tough. It's very high volatility. It's a high stress job. So I think that's also really hard.

I think that particularly being a woman in the game is incredibly difficult as it is in any environment where, you know, on the for professionals, I think it's like three to five percent of people who play poker who are professionals or women. So I think anytime that you get that kind of imbalance, I think that's a really difficult place to be as a woman. So I think that's also like incredibly hard. The good things are like you don't have a boss. It's kind of nice. Make a lot of money, which is nice. And for me, I was playing a game that I loved, which was also nice. So for me, I retired at the point that the bad stuff outweighed the good stuff. And probably after that point, as people do, like it's you tend to be slow to quit things,

particularly ones that are wrapped into your identity. As mine was, people still think about me as a poker player, I think, and I haven't played in 10 years. If you asked somebody who was in a touring band, the same question, I think they would give a very similar answer to me. Like you're doing something you love, but it's very hard not to have a home base to be traveling all the time,

to be in different hotel rooms. That kind of stuff, I think, here's sort of a very similar thing. This is the Passion Struck podcast with our guest, Annie Duke, we'll be right back. This episode is sponsored in part by Shopify. Here that little chitching, that's the sound of another sale on Shopify.

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You can check out all our sponsors at passionstruck.com slash deals. You'll find all the codes, all the URLs, all those things are there. So please consider supporting those who support the show. Now back to my interview with Annie Duke. I actually have a friend who was the league guitarist for a pretty darn big band and he said the same thing and he got out of the band after I think their first or second album, but it was primarily because of the same thing and he had kids and it just became too much. But yes. Yeah.

But where I wanted to go with this now is going deeper into the book. And we've already covered some concepts from it. But you start out the book by discussing Muhammad Ali. And what I wanted to ask is how did that same grit that helped him become a champion revered without equal become as undue when it was obvious everyone who was on the outside looking in that he should quit. Yeah, so look, here's the thing. I think that we all revere grit. The people who stick it out are the

heroes of our story. We admire people who keep at it even in the face of huge obstacles and big downturns and naysayers. And when we think about grit, we think about it as a virtue, right? Like, look, let think about grit, we think about it as a virtue, right? Like, look, let's be honest, we think about it as synonymous with character. Right, like if we're gonna build character, right? Then we wanna be gritting. We tell that to our kids, like you can't quit

because you need to build your build character. But I think that what people forget is that grit kind of period can't possibly be a virtue that the context matters like for your friend, right? It's not great that he's gritty in this particular case. He ought to be walking away. So grit absent context is not a virtue. You need to know what the context is within which somebody's persevering. Because while grit is really amazing for getting you to stick to worthwhile things that are like really hard, it's also really amazing again getting you to stick to things that are no longer worthwhile. And I think with

Muhammad Ali you can see this like in a single individual. So Muhammad Ali started off boxing as cashless clay. Could have obviously the greatest of all time, Muhammad Ali, but he started off as cashless clay at, which was a given name when he was born. Beat sunny, listen as an underdog. Beat sunny, listen for the heavyweight title. And he was so smart. And so I mean, he was quick on his feet and quick of mind He said like he's holding was like float like a butterfly sting like a bee because he was so fast

That it was very hard to land a punch on him and then he would just come in and sting you with a punch and so he beats any list in And then soon after that the Vietnam war starts he converts and becomes Muhammad Ali and as part of that He is a conscientious objector to the war, so he refuses to be drafted, at which point he gets stripped of his heavyweight title and he's not allowed to fight. So eventually, after I think it was four years, he was allowed to fight again, I think the war ended and he could get back in the ring. And when he was allowed to get back in the ring, it's not like they were just like, oh, and by the way, you're still heavyweight champion of the world. They said you got to earn the title fight back.

And it takes them, I think, was four years to get a title shot, to earn the right to win the title back. So by this time, he's in his early 30s. And that's quite old for a boxer, but he gets the title fight against a guy named George Foreman. And George Foreman, I mean, I think sort of people think of him as the guy with the grill, but when he was a fighter, he was really good. He was ginormous. And his fights never lasted, but a handful around. Because he was just so big, he would just come into the ring and just knock his opponent out. So he's undefeated.

Ali obviously is old for a boxer and not as fast as he used to be so on so forth. So he's a big underdog going into the fight, the rumble and the jungle in the Philippines. So he comes in and he changes his strategy. And instead of float like a butterfly sting like a bee, he goes to Ropadoop. And Ropadoop is basically, look, this guy is as good as he is. Hasn't ever gone more than a few rounds.

So I believe him to have no stamina. So if I can just last and let him tire himself out, I'll be able to win this fight, which is what he does. He lays against the ropes and Foreman just pummels him. But as Ali had planned, Foreman tires himself out, but the fight goes like the distance. I think at that time, fights were 15 rounds. So this is a very long fight. So Ali's taking like a lot of punches, right? But anyway, he ends up winning the fight doing that. He does actually tire forming out and ends up winning the fight. So that's great. So here we can see what grit does for you. Right? I mean, here's a guy goes in and fights listen. Nobody thinks he's

going to win. He wins. He sticks to his guns. He's gritty, right, about his faith. Being a conscientious objector to the war. That's amazing. Then he comes back and has to fight his way back after being heavyweight champion of the world. He's some four years to do that. That's super gritty. And he goes in a fight to our foreman in a spot where nobody thinks he can win. also very gritty. So let's admire that. That's amazing. But what people don't know is the rest of the story. They know that part of the story. Right, but they don't know the rest of the story, which is he kept fighting.

And he kept fighting, even though he was getting older and his new strategy was to take a lot of punches. And there's only so many punches that a body can take. So what happens is Teddy Brenner, who was the fight promoter at Madison Square Garden, and a very good friend of Ali's, but let's be honest, making a lot of money off of Ali. Okay, so if he hosts an Ali fight, he knows he's gonna fill, he's gonna fill Madison's square garden, he's gonna make a lot of money. But he's Ali's friend. And he can see that there's some neurological decline happening.

So he says to Ali, look, I think you really need to stop because I'm worried that someday you're gonna come to me and you're not gonna remember who I am. And I'm gonna feel like it's my fault that me and you're not going to remember who I am and I'm going to feel like it's my fault that I allowed you to keep going. So I need you to quit. So Ali says no. And Teddy Brenner quits him. He says, okay, if you're not going to quit, I'm not hosting your fights at Madison Square

Garden anymore. I can't be part of it. So this is a friend who's giving up some financial upside in order to protect his friend. But Ali says no. So a little bit later, I think it might have been a week later, there's an x-ray that comes back that shows that there's really bad kidney damage occurring. So Ferty Pateko, who is Ali's fight doctor, Also Ali's friend says to a you need to quit. Your body is getting damaged. This damage is going to be irreversible. You need to stop. And Ali refuses. And Ferdi Pateco quits him. So this is something. So he keeps going. And it's just a disaster, right? Like he he fights Larry

Holmes and gets beaten up so badly that Larry Holmes actually cried after the fight. He loses to Leon Spinks and Leon Spinks is seventh fight as a professional boxer and finally ends up and we couldn't even get licensed in America by the end. And he ends up overseas in a fight where they only have two sets of boxing gloves. So everybody has to wait to take the gloves off the previous card. I'd like to undercard and put it on your hands. And I mean, he even loses that. And eventually he just couldn't get licensed anywhere. And he was forced to quit.

I think this is really important to understand. It's like sometimes when people are naysaying, sometimes when things are hard and other people can't see the way out, you do actually see something they don't see. And then grid is amazing. But when the world is screaming at you to quit, I don't think you see anything that they don't see. And then grid becomes total folly. And we know what happened to Muhammad Ali in the end. He ended up with Parkinson syndrome and it was really sad to climb as somebody who was like the most sharp-witted human at the time. Yeah, you see him in his interviews from back in the day and

wow, did he have wit and charisma and everything else. But yeah, I remember watching him as a kid when he was in those early fights. And even when he did the George Foreman one, but you're right, his whole tactics changed. But it's a great example of staying in for way too long. You also raise another good example, Lindsey Vaughan, who put her body through just battering after battering, as she kept recovering from her multiple injuries as well. But I'm gonna jump to the second part of your book, because since she brought up the Vietnam War with Muhammad Ali, your second part of the book

is talking about being in the losses. And what I wanted to ask is, how were the examples of the book is talking about being in the losses. And what I wanted to ask is how were the examples of the Vietnam War in the war in Afghanistan, places where we're in the losses, and because of that, we're more likely to stick to a losing course of action. Well, I mean, we can talk about the war in Ukraine as well. I mean, this is so very star who's one of the giants in this field of escalation of commitment was inspired as well as quite a few other scientists, including Jeffrey Ruben by what was happening in the Vietnam War to start really looking into this idea of escalation of commitment.

Because what they noticed was that, like there was no point at which we could have possibly had any illusions that we were winning that war. I mean, it was never going very well. And what happened with despite all of the signs that this was not a war that we're going to win, we kept going. It was very hard to extricate ourselves from it. And he had read the Pentagon papers, which it got leaked, where Under Secretary of State George Ball had basically said, we need to really not start this war because once we start it, and we start to incur losses,

it's going to be really hard for us to extricate ourselves from it. So he had really sort of foreseen this problem of escalation of commitment. And in war, it's particularly difficult because not only are you spending tremendous amounts of money on the cause, but you're also losing lives to the cause. So if we want to think about kind of like the ultimate

sunk cost, think about a life lost in the cause. And actually, General Tony Thomas said to me when he was talking to gold star families who had lost their children in Afghanistan that he said it's really hard when someone sort of grabbing you by the lapel and saying go win this war because I don't want my child to have died in vain. lives in these endeavors. What we have to remember, as it goes with other resources, the resources of human lives, it's true for these as well, that what you've lost to the cause doesn't mean that you should put another life at risk going forward. Not if you don't believe that the war is actually going to achieve your objectives, and I don't think there was any point for Vietnam where we felt that we were actually going to be able to achieve our objectives. But here we were mired in it, right? Because it's very hard to walk away because then everybody feels, why did you get into it in the first place?

What about my child who died? And then you just walked away from the war? What about all the taxpayer money you've spent? And then you didn't even accomplish anything that just puts you in a situation where these things go on way too long. And we can certainly see that in Afghanistan. We were there for 20 years. What did that do for us? The Taliban took over in three days once we left. And but what's interesting is that if you look at the reaction to the actual exit from the war, People lost their mind. So theoretically they kind of understood, like, oh, maybe we should try to get out of this war. But when it actually happened, people were mad. How could you exit with no plan to not have the Taliban take over? Well, that shows that we weren't winning the war. So then you can also add in on top of that, there are just issues of national identity.

So Barry Stott talks about this issue of what's called external validity, right? How do other people view you? And it's a very important motivating factor for the types of decisions that we make. And it certainly motivates us around not quitting because we feel like if we shut a project down or your friend like shutting a business down,

then it's like, you failed. Why did you start this in the first place? You wasted everybody's resources. You worry that the investors are going to say you wasted my money. And in war, it's like you're worried that everybody that taxpayers, whatever, think about it as a politician, right? I'm going to say you wasted my money. Why did you get us into this in the first place? That the world is going to be laughing at you. All of these things, right? That makes it very hard to walk away. Then if we look at the war in Ukraine, we can see all of this stuff happening.

I mean, tell me what point Putin's been winning that war. Because I mean, he was supposed to take Kiev in three days, so I'm not sure that there's a point that Russia has been winning that war, not in any real sense of the word, but look, I mean, it's lots of money hundreds and hundreds of million dollars in weapons that they've expended there. Obviously, so many lives lost. And for him, national identity, right, like the identity of Russia going against the rest of the world, Putin's identity as a politician, so on, so forth. And you can see that he keeps escalating his commitment to this losing cause,

conscripting people, so on, so forth. So I think it's interesting when people are saying, like, what we need to find an off ramp for him. And I'm like, what's the off ramp? Because any off ramp that involves him not winning is not going to be acceptable. It's just kind of not acceptable in a war. So what ends up happening with wars is that you've got to get to some sort of point where essentially you don't have a choice. So either you win whatever that objective is, so the

other person surrenders, okay, so that would be winning, or you have to get pushed till you don't have a choice. So in America for the Vietnam War, I think it was just very clear that no politician was ever gonna get reelected if they supported that war. So that can get you out of it because you're sort of pushed against. Essentially, you're trying to get to, I had no other choice. And I think that that's what happened in Afghanistan. And I think that's the only way that Putin's gonna exit

is one of these I had no other choice. So I would say that it's more likely that Putin leaves the work as he gets deposed than if he takes some sort of off-ramp. Yeah, I mean I think for the United States it's always our center of gravity. He has always been public opinion. When it comes to these wars, but I think one of the things that at this point is keeping Putin alive is he is basically not telling the truth to his population and the other thing is since no one has taken the war to inside of Russia, they're not feeling the pain because in many ways it's invisible to them unless they're one of the people who have lost the tens of thousands of lives from it. Before we started, I mentioned to you that I hit interview Daniel Pink earlier this year about his latest book, The Power Regrets. And as I was reading your book, I found that regret is very similar to the topic of quitting. Why do both have such a negative connotation?

These are both associated with losing or failing. I think that's why. What are the things that we regret? The failures. If we quit, when we're in the losses, right, if we quit when things aren't going well, that is the moment that you go from failing to having failed. But if you have a business that isn't doing well, as long as you keep doing it, you have a chance that you might turn it around. Now,

as poker players would say, but not enough of a chance, but any chance for us there feels better than as long as it's not zero, we have this urge to push ahead because when we quit that's the moment that we failed. That's the moment we look back and regret, right? So I think that when we think about failure, it has a such a negative connotation that these things that are associated with failing, like quitting, regret, take those negative connotations on as well. But I don't think of quitting as failure at all. I mean, that's one of the things. It's just similar to what Daniel Pink says. Like, is regret really negative?

Like, or does it really drive us to learn? I don't think quitting is a failure. Here's the situations under which I think quitting is a mistake. When things are going really well. And what you're doing is actually causing you to gain ground toward your goals and you quit. Okay, I'm not sure why you would do that, right? I mean, assuming that you're not quitting to go do something that's going to cause you to gain even more ground toward your goals. Now notice I'm not saying that you were in a job, we're making a lot of money and then you quit to go take a job that was 40 hours a week. I'm not saying that's a failure

because I said it's your goals, right? So I would actually consider it a success if you decide, you know what my goal wasn't to make the most money. My goal was to spend the most time with my family. So in that case, if you quit, I think that's a total success. So the only failure is when you quit, when it's a bad time to quit, meaning things are going really well and actually you're just reading a situation wrong if you quit. But anything else, like if you quit, when things aren't going well, I don't know why that's a failure. In the same sense, if I'm driving on a road and there's a huge accident and traffic is really slow, is it a failure to exit the highway? No, because I'm going to go get on a faster road. That's really good decision making. That's success. And I think

that we need to start seeing it for what it is. The failure is Muhammad Ali continuing to fight after Fertipotko and Teddy Brenner quit him. That's the failure. So we need to stop thinking about quitting as a failure because sometimes not quitting as a failure too, we just don't think about it that way. Yeah, I was gonna bring up a couple examples of that. One that's not in the book, but I think is a great example is famous football

running back for the Lions,berry Sanders ends up quitting. And at the time everyone is so mad and if he would have stayed in, he probably would have been top greatest running back of all. Yes, he would have been the goat, but he's looking at the toll that it's having on his life and looking at other players who have CTE and other things going on, and he makes the decision to get out, which from his standpoint probably turned out to be a very excellent choice. But I like in the book how you bring up the story of the comedian Dave Chappelle, who left production of season three of his popular show.

And I recently interviewed Dr. Benjamin Hardy. I'm not sure if you're familiar with him. He also does a lot of things around behavioral science. And his latest book is on the science of your future self. How did Dave Chappelle use the power of looking at his future self as a way to decide that it was time to quit? Yeah, so actually, interestingly enough, kind of the only way to really quit well is to be able to get a look at your future self.

Because quitting is a forecasting problem right that the moment that it's correct to quit it's not going to be like anything particularly dire is necessarily happening right then. That's going to be that you can see that what's going to happen in the future is not going to be good so you can take Barry Sanders is an, right? He quit at the top of his game and there are a variety of reasons that he might have looked into the future and seen that. So as an example, CTE, right, he might have seen like, oh, I really don't want to have all these concussions and that's going to be bad for me in the future. Or my body's taking too many blows and I want my knees to still work when I'm older. Or maybe it was just that he said, look, at some point I'm going to be sure that I'm not playing well anymore work when I'm older. Or maybe it was just that he said, look, at some point I'm going to be sure that I'm not playing well anymore.

And I've seen a lot of athletes around me who play past the point, at which they really should be on the field anymore. And I don't want to be that person. I don't want people to see me on the back end. So there's all sorts of things, but that's all sort of looking at what's going to happen in the future.

Because at that moment, he doesn't have CT at that moment his knees work fine. Right at that moment he's playing really well. He's just looking into the future and that was true for Dave Chappelle as well. So Dave Chappelle walked away from this huge contract. And for him, as he said, like a comedian is supposed to get up and like tell jokes, he's not supposed to be the joke. And he was going to do stand-up gigs and people were yelling characters at him from his show, asking him to do characters from his show. And he just realized like, I don't wanna be the show. I don't wanna be the joke. I wanna get up to be the show. I don't want to be the joke.

I want to get up and be the comedian who's just sort of delivering the jokes, right? And then people are thinking, it's funny. I don't want to do characters. That's not really what I want to be for the rest of my life. And he just realized that it was just making him very unhappy. And then it was going to get worth. Right. And so he walked away. And the thing that's so interesting

is that we as observers hate that so much. That people started saying that he was in a mental institution, that he was addicted to drugs, like all sorts of things, just to try to explain what they felt was really bizarre behavior. And you can see that with Barry Sanders too. People still are kind of mad at Barry Sanders for not continuing to play, even though it was obviously the right decision for him.

But here's the interesting thing where you've got to, so I've seen the commentary about Tom Brady and Aaron Rogers this year. I think we all know what the commentary for Peyton Manning was in like his last year. Drew breathe, yeah. True breathe. We're all like, oh, what an idiot. Why did they keep playing? Like, oh, Tom Brady's having a midlife crisis,

all of these things because they're playing past the time that they're the best versions of what they have been in their life. And we get mad at that too. So what is a person to do, right? Like, if I quit at a time where it's not obvious that I should, you're gonna get pissed. But if I stick around to the point

where it's obvious that I should have quit, you're also going to be pissed. You're gonna make fun of me. So this creates like a huge bind for people in quitting. And I think in the end, just for ourselves, we tend to want to be sure that there's no other choice. But from a public facing standpoint, there isn't a great way around this.

And I think that what people forgot is everybody has different values. They have different things that they're trying to accomplish. And I mean, Tom Brady might really enjoy playing football, even if he's not that good at it anymore. And Barry Sanders might have really valued being able to walk. And Dave Chappelle might have really valued

going back to Ohio and getting some time with his family and getting back to a point where he could do stand up without people yelling characters at him. And I think that all of that's fine. And we shouldn't be judging people for those choices in that way. Well, given I live in Tampa Bay, a lot of my friends would probably argue,

well, he stole from the top five quarterbacks this year, but I personally have seen a drop off as I've observed him play this year. Well, that's the thing. I mean, look, we benchmarked or whatever we benchmarked. So is he as good as he used to be? No, but again, like we don't know what his values are. I don't think that you can say that he's sticking around too long because it completely

depends on what he wants from football, Not in the way that we can say that Ali stuck around too long. Because I think Ali objectively stuck around too long when people are telling you like you're, were medical professionals telling you that you're experiencing neurological decline and your kidneys are not functioning. Now we can objectively say that continuing

to take punches is a bad decision. It wasn't a bad decision for Peyton Manning to play his last season. I mean, I assume he really liked football. So whatever that balance was between like, I want to be as good as I used to be enough, but I also want to be on the field every week. For him, that was probably a perfectly good decision. I think that's just we shouldn't assume that we know what the answer is. I think he just wanted to equalize his brother's accomplishment of winning two Super Bowls. How could he ever live that down?

Well, throughout our discussion today, we've talked a lot about individual examples of this, but I wanted to close on one of my favorite chapters, which chapter eight and you profile the rise and fall of series robot. Why is it such a great example that the hardest thing to quit is to quit who you are. Yeah. So we've talked a lot about what it means to be in the losses meaning I put time and energy money into something and if I quit that will be for not I won't be able to get a back all of wasted it but sometimes Money isn't the problem where effort isn't the problem or time isn't the problem what you've put into something and Rather the problem is your identity because there are certain things that we walk away from in life But where we're actually kind of walking away from who we are

Right, so for me as a poker player, quitting that was hard because people knew me as a poker player. Like, and you have these feelings of like, well, if I walk away, like, well, am I going to be? What does that mean for me? Yeah, think about. Yeah, think about Serena Williams or Roger Federer. Who, by the way, Serena Williams refuses to say she's retired and she said she's evolving, right? I mean, that's how much we hate that, right? Lindsay the Lindsay von Pente. She said, I'm stopping skiing, but I'm not quitting.

It's like, what do you think quitting means? Because that sounds like quitting to me. We're so averse to it, and it's very hard to walk away from our identity. And it's not just hard for individuals, that's the thing. It's hard for companies as well. So I think we know there's like a story of series that we all know. It was founded in the late 1800s,

the book of bargains, Sears and Robuck catalog. It was huge, right? Like it was the biggest IPO ever, still to this day, I think, for Goldman Sachs. And it was Goldman Sachs of Morgan Stanley. I can't remember which one. And then in the 20s, the founder, Sears, was worth like $26 million.

Like it was, it was- On the money back then, yeah. Just a lot of money back then exactly. Sometime around the 30s, the catalog was sort of using this new likefangled thing called mail that kind of went everywhere and into rural areas. And so they were trying to get

products, the ability for people in rural areas to be able to buy stuff that normally would only be able to get in a city. So think like a bicycle, right? Because that rural areas don't have a lot of access to the kind of goods that are available in the cities. And that's where they developed the Sears Robot Catalog. So in the 30s, people got cars and people started driving places and they didn't necessarily need a catalog as much because they could get to places to go buy things. So Sears then created retail locations. And just like the Book of Bargains, you could really buy anything. Right? You could get like underwear or a wrench or a bicycle or a refrigerator, right, like shoes. I'm at anything that you could imagine.

You could get it a sear store. But those retail locations were incredibly popular. They were very successful. By the 1950s, sears represents 1% of USGNP. That's pretty nuts. That's a lot. But then by the late 70s, you start to see these competitors come into the space, right? So you get Walmart, you get Kmart, these very low-end

discount retailers. And then you also have the high-end retailers come in, like Neiman Marcus, Nordstrom, Staxbeth Avenue. Home Depot and Lowe's as well. Yeah. So what happens is that Cier sort of starts to lose its place in the retail ecosystem. They're really kind of not really a bargain retailer, but they're also not a high-end retailer

and so they're trying to sit in the middle and it's not great. By the 90s, they're no longer the number one retailer in the country. Walmart and Kmart have beaten them, targeted on its way. They very slowly go into insolvency at one point actually in the 2000s. They merged with came art, which by that point had also been pushed out. And I think somebody called that a double suicide, a hedge fund eventually invests in them, and then they go bankrupt. So that's kind of the story that we all know of Sears. But there's another story of Sears, which is like so incredible, which is Seers was not just a retail store.

It was also a financial services company. So originally, I had a banking department because they were often customers credit. But then in the 30s, as these cars came along, so that's why they created the retail locations, they also realized that people might need insurance for these cars. And so maybe they would buy that insurance at a seers store that they had driven to. So they found it a company called Allstate Insurance. And Allstate Insurance had their offices were literally in the sear store. So now you could get an underwear wrench and car insurance. Photograph.

Yes, and your photograph. And it was it was thriving. And eventually, obviously, it moved out of the actual Sears location and goes on to become the largest personal liability insurer. So they have that that they founded. And then in the 70s, they acquired a company called Dean Witter, which was a stock brokerage, actually. And somebody made the joke about Sears that you could get stocks and stocks at Sears stores.

So then there's Dean Witter, which is a huge financial services company. It's a stock brokerage. They also found the Discover Card, OK. And they get Coldwell Banker. So the question here then becomes, if they had Dean Whitter discover, Coldwell Banker,

and all the state insurance, how did this company go bankrupt? Because that's kind of confusing. If you look at the combined market cap across those four entities, you know, obviously, you have to estimate with some of them because Dean Wetter doesn't actually exist anymore. They got acquired. But if you look across all of them, it's somewhere close to $100 billion in market cap. Yeah, but the identity of the company was the retail store.

That's right. So when the retail stores start to falter, they now have a choice. The shareholders are demanding action. They're demanding that something be done to save the company. And they have a choice. Should we keep these assets that are losing money, the retail location, or should we keep the assets that are making money? Dean Witter discovered Colo banker, I'll stay. Now from the outside looking in the

answer to that seems obvious. Well ditch the retail stores, they're doing really badly, sell those off, and keep this other stuff. But if they do that, then they're not a retail company anymore. And their identity was retailing. That's what they were founded as, a retailer. So when it comes pushed to shove, the board says, we've decided to get back to our retailing routes. So Dean Whitter Discover gets acquired by JAP Morgan and Morgan Stanley. I'm clear exactly what that was worth,

but it represented 40% of the value of that entity at the time, and that's a very valuable entity. So it's a lot of money. All state insurance, they spin off. So they spin it off in a separate IPO in order to raise funds to shore up the retail business, and they sell Cold War Banker. And we know what happens after that. Those companies thrive, and Seers go out of business.

Why? Because they want to protect their identity. They want to get back to their retail and roots. I mean, obviously, it looks like a nutty decision. But the thing is that we all do this. We're all trying to protect our identity every single day of our lives. And this is particularly true when we start to think about beliefs that we won't let go because we identify with those beliefs,

think political beliefs that in the face of lots of evidence, people won't jettison because they would have to jettison something that sort of defines them as Republican or Democrat. The thing about me as a poker player, one of the reasons why I probably stayed past the time that on be with making me unhappy is because who was I supposed to be then? I'm a poker player, right? I was. And when the thing is, of course, like when you actually quit, you're like, oh, this isn't so bad. And as we said before, I neither watch

nor play poker anymore. And I'm fine. I'm still me. But it doesn't feel that way when you're, that's part of the problem. So I think that we can all take a very good lesson from Sears about how identity makes it very hard for us to actually quit things. Okay, and then my last question, Annie, will be, if there's a takeaway that you wanted a listener or a reader of the book to get, what would it be? I think the takeaway is just that quitting the ability to quit and quit while is at least as important a character trait as sticking to things because your goal in life is to stick with the stuff that's worthwhile and quit everything out. And what that means is that over the course of your life

There's going to be a lot more quitting going on than sticking. And I think that just the popular narrative around grit has been that we have a belief That the human condition is one of not sticking to things enough That we're all kind of quitters, right? And if you're not eight years old, that's just not true. Like if you're 28 instead of eight or 38, your problem is you stick to things too long in general, mostly. So you need to flip that script and stop thinking that sticking in a job with a toxic boss

somehow is showing character. That continuing up a mountainous no-storm is somehow showing character that continuing to box after you're getting these medical reports is somehow showing character. It's not because in that case, you're just slowing yourself down because you're sticking to something that is not working. And that is sacrificing all the games that you could be getting from other things that you could be doing that would be that would win, that would actually be getting you to achieve your goals. So if you want to be quicker to achieve your goals, you need to start being a better quitter because you have to quit the stuff that is not getting you to achieve your goals

so that you can switch to something that is. And when you find that thing that's going to help you achieve your goals, then you want to be gritty, but only that. Well, Annie, thank you so much for coming on the podcast today. And I will just tell the audience, this is an incredible book. I love it. We only got to touch the tip of the iceberg. There's so many elements of science in the tip of the iceberg. There's so many

elements of science in the book with great explanations and Examples that really bring it to life and I didn't even get to talk about the partnership that you had with Daniel Canemun and Richard Thaler and Dom Moore and some of these amazing behavioral scientists who Took the time to review and give you suggestions all the way along. So I love that it's got all their endorsements. But thank you again so much for being on the show. Well, thank you so much for having me. This was a fun discussion. I hope your friend shuts his business down finally. We will see. I don't give that very high chances. Okay. Well, that was an awesome interview today with Annie Duke. And I wanted to thank Annie,

Hady Melpin, and Portfolio for giving us the honor and privilege of having her on today's show. All things Annie will be in the show notes at passionstruck.com. Please use our website links if you buy any of the books from the guests that we feature here on the show. All the proceeds go to supporting the show. You can find our videos both at PassionStruck Clips as well as our main channel, John R. Miles. Avertise their deals and discount codes are in one convenient place at PassionStark.com slash deals. I'm on LinkedIn and you can also find me on Twitter and Instagram at John R. Miles. And if you want to know how I book amazing guests like Annie Duke, it's because of my network. Build those relationships before you

need them. You're about to hear a preview of the PassionStark podcast interview that I did with Oksana Masters, the United States most decorated winter Paralympic athlete about her journey from a Ukrainian orphanage to the podium. She was nominated for three SB awards this year, including Best Female Athlet athlete. We launch her absorbing and try often new memoir, the hard parts, a memoir of courage and triumph. It really all started turning around where I started realizing that I'm going to make this dream real because of all the negativity that kept coming and everyone determining so much for me. And I guess maybe my dream was starting to advocate for myself. And that's by doing it by

showing and not just trying to fight back with words, but just prove people what someone with no legs can do and a girl can do or that you can come through these really messy, horrible experiences and be use those horrible sad things or the bad days as fuel and be that secret weapon to guide you where you want to go. Remember, we rise by lifting others, so share this show with those that you love and care about. And if you found today's episode useful, please share it with somebody else who can use the advice that we gave here today on the show.

In the meantime, do your best to apply what you hear so that you can live what you listen. And until next time, live life, Ash and Scrap. you