The Daily Stoic - Annie Duke on Knowing When to Quit

Episode Date: October 19, 2022

Ryan talks to World Series of Poker champion Annie Duke about her new book Quit: The Power of Knowing When to Walk Away, the power of walking away from things that don’t align with your beliefs, the importance of making decisions in service of a larger goal, and more.Annie Duke is a former professional poker player and a bestselling author. She is an expert in cognitive psychology and co-founded the non-profit Ante Up for Africa in 2007 to benefit charities working in African nations. Her recent book, How To Decide, details how to be a more confident decision-maker. 📕 Ryan Holiday's new book "Discipline Is Destiny" is out now! We’ve extended the pre-order bonuses for the next week—among them is a signed and numbered page from the original manuscript of the book. You can learn more about those and how to receive them over at Dailystoic.com/preorder. ✉️  Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Hey, it's Ryan Holiday. Welcome to another episode of The Daily Show Podcast. I don't think we've had many people on the podcast more than twice other than the one in Only Robert Green, but Andy Duke is one of my favorite people and one of my favorite writers. And so hearing that she has a new book on a topic that is near and dear to my heart as a college dropout, I really wanted to talk to her. Her new book, Quit the Power of Knowing When to Walk Away, just came out. I've also loved and raved about her book, Thinking in Betts, which I carry here at the Pay and Report.

If you haven't read, you should absolutely check that out. As a former professional poker player, she's won millions of dollars in poker tournaments. But I think where her most important work has come is in thinking about decision-making, thinking about the lessons and metaphors of the game of poker and how we bring them into everyday life to be better at the game of life. She is also the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education, which is also on the board of the Renewed Democracy Initiative, which I think is really, really important.

Here's my conversation with Annie. Do check out her new book, Quit, The Power of Knowing, Win To Walk Away, published by the same publisher I have portfolio. It's a great book. And if you haven't read Thinking in Betts, you absolutely should. And her other book, How to Decide. It's also quite good. Recommending all of Annie's stuff stuff if you haven't read any of it already. Any of those is a good place to start. Go to her website at AnnieDuke.com or follow her on Twitter at AnnieDuke. How are you? Well, I'm good. How are you?

I'm doing good. I was just saying off camera, I'm getting it on the record. So people don't notice, but my kid drew it all over my shirt. So it it looks, it's this isn't the best presentation. Well, I have four children. So I remember just being covered. I know what that's like.

Stuff is just always coming out of their mouth, always coming out of their nose. It's just it's just a stream. of their mouth always coming out of their nose. It's just it's just it's just a stream. Well, I'm very excited to talk and grats on on another book also. Same to you. Yes, yes, I think I think you're you and I are perhaps the two most prolific portfolio authors like I feel like I feel like we're we're keeping them busy over there. I feel like I'm a very I mean if I am I'm a very distant second to you. I just have to say that it's just astonishing but at first I would personally never commit to write a book a year so like kudos to you impressive but I'm not sure I would commit to that again either so well there you go fair. We learn, right? I've been on

an every two year schedule so far. It's not so bad that I would quit to go to the topic of today's conversation, but I definitely learned that more space is better. It's actually, it's less the writing that I don't have room for. It's this, it's less the writing that I don't have room for. It's this, it's the hardest part has been like, I'm now in the middle of writing the next one, but I've had to stop and go do stuff that's not writing. Yeah. So when I was, when I had finished quit,

the draft, which as you know does not mean you're finished. No, it's like half-wit. Right. So, be able to know, like, you turn in the draft and then you get big suggestions about kind of broad edits from your editor. You implement those, then it goes through like 17,000 copy edits or so. I'm not sure. Yes.

Because even when I, when I was reading the advance copy of discipline is destiny, there were, you know, there were some typos I was finding in there. For sure. Just takes a, Thank you for catching them. No, well, I mean, it just takes a village because you can read the same thing over and over again,

but you then have an expectation of what you're reading. And so it then becomes very hard. So you have to do that like four times. And I don't know if you do, but I record my own audio books. You're catching errors even when you're reading it for the audiobook. That's exactly right. It's like, oh no. So, but when I had turned in the draft, I knew that things would slow down a little bit, right? Like, because the actual process of like drafting a book is like very intensive, like cognitively physically everything.

So I decided that I was going to take two and a half off, sorry, I decided I was going to take like two and a half months off of my clients. So I also have a business consulting life. And I just told my clients, you know, I'm turning this draft in, you're not going to talk to me too enough months. Yeah, because I just needed some space. It's exactly what you're talking about is that I felt like I when I was promoting how to decide my last book, I was already thinking about quit. Yeah. And I had already started doing the research for it. I was talking to a bunch of people about it. I was writing the proposal at the same time. I still had my clients that I was working with. I was doing research at Penn with a couple of people.

And I just sort of after I finished the draft, I was like, I need a second here. I need some space. And I spent two and a half months basically like, separate apart from like reading the drafts and still working on some of the stuff that had to do with my research, walking with my dog to the river every single day,

and like playing tennis. Yeah. And it was amazing. And I just said, you know what, I have a bunch of stuff on my plate right now, I've got a releases book into the world and I've somehow decided to go back and do my PhD, which I thought was like ABD before I was just shy of it.

And I said, as soon as that's done, my next project is to think about what does it really mean for me to be productive? And to your point, this realization that like space away from at least what I think people would traditionally think of as productivity, which is your work product, is actually incredibly productive. And I want more of that. And so that's my thing in the spring. It's I'm gonna be working on space.

Why I talk about Joyce Carol Oates in Discipline Estesne a little bit in her rule. And it doesn't, she's so prolific, I'm not sure she actually follows said rule, but I think there's value in it. Her thing was that she likes to leave the manuscript in a drawer for a year before she goes, begins the publishing process on it. Because just sort of sitting and thinking about it and but also not thinking about it. Having the space for like, you know, comedians talk about tags or like, you know, just the

little things that you add in there that actually, you know, that last 5% might make all the difference was really important. And there's a quote I found from Lincoln where Lincoln talks about even just those couple months where he writes the emancipation proclamation, but then he's waiting for the moment that he has the political strength to put it out. The language changes significantly. And I do think that space is really important. It's just so hard to budget for it because it feels like the opposite of work. If you're like, I need two more months to write,

people would give you the space. If you're like, I need two months to not write, people would be like, what is that even? Mind? Yeah. Yeah, you can justify one. It's hard to justify the other.

Even if the other is actually the one that moves the needle. Yeah, I wonder, you know, it's interesting. So, you know, it, quit took me from inception to turning in the draft. So this was before I was writing. I mean, I wrote a proposal, which is still writing. Sure. It took me about a year from proposal to writing. And then there was about three months in front of that,

where I was really working on it. Sure. And, you know, I always wonder, if I sort of sat with it and took a little bit more time, would it actually be a better book? And the thing that always worries me is that there is no book where I don't wish that I could go back and change some stuff. Particularly when you're like doing podcasts about it and you're talking about it, it creates like kind of a workshop for the ideas and trying to figure out like what's the best way to express it, how are people going to respond to it the best. And I just am not sure that putting it in a drawer for a year would change that.

Do you know what I mean? Like, I don't know that I would have less regret because the world, you know, I mean, this is part of so much of what I think about and in my writing is the world changes, like your knowledge changes, you change. And I think that no matter how long I sat it in a drawer, that there would always be some, you know, something that I would want to go back and say differently, or

there'd be new research that came out, or I would have talked to someone and they expressed something way better than I felt that I had in the book. So, you know, I feel a little bit like that's where that editing process comes in, like I want Nikki, pop it up, a list of my editor, to like take a really good look at it. And I actually make sure to send her along the way, like send her chunks along the way, because I want to hear what she has to say. And then I have like readers who are reading it

to try to solve for that problem. But as soon as I get to this, as soon as I get to the public conversations about it, that's when the regret starts to set in. So yeah, and I'm not sure you could have that, those conversations without an imminent ship date. That's right. So like the real valuable part of the process may just happen after completion, whether it took three years or a year and a half. Yeah. And like, I remember as a kid, you know, they'd be like a math tester, whatever. And I was all, I

would always be like one of the first people to turn it in, the teachers would be like, are you sure? You know, they'd always be like, are you sure? And I wasn't like, cause I was good at math. I just tend to do things quickly. And I sort of get done what I'm gonna get done. I do know I have the issue of rushing things

and that like, you know, if I'd taken them slower, if I'd measured twice, I'd cut less or whatever, but I generally find when I look around the industry that the vast majority of people have the opposite problem, right? They take too long. And when I look at someone who took four years on a book, very rarely, like when I look at Robert Green or I look at Robert Carrollro or, you know, you know, this is some of the greats, I can see where the five years are. But most books that I look at where the people are not as productive and they do take longer,

I'm not like, it was, you definitely used the whole shot clock here, right? Like, yeah, I'm not seeing the painstaking results of taking more time. So there may be a certain amount of just like balance here. I think shipping is the harder problem than shipping. More people fail to get over the hurdle of shipping than the people who ship too soon or ship more than they should. Well, I mean, I set Goden would obviously agree with you about that. You know, I think part of the problem is this,

like if you think about identity, the identity of I'm writing a book is like a super awesome identity to have because everybody thinks you're bomb. Like oh. It could be the greatest work of all time. Right. Like people just think like, oh my gosh, I wish I could write a book. That's amazing that you're writing a book.

They just think you're totally awesome. The act of shipping a book, that's terrifying. That's when you're running down the street naked. So I just always kind of think about, I'm gonna have a bias against putting it out there because that's when people, it's open to criticism. Now, obviously, there's only so quickly that I can write a book like, you know, any of my books because there's

a lot of research that goes into it. As with you too, right? Like there's just a whole bunch of stuff you have to research. You're not you're not writing chicken soup for the soul, which is like thoughts that are coming out of your head. You know, for somebody like, you know, like Robert Green,, there is a tremendous amount of research for people who are doing biographies. You have to take the time to really get the facts right and talk to the right people. You need to give time and space for that, so you don't want to go too fast on that. But I think that going back to that idea of like, am I always going to regret things that are in the book, sure?

So is putting it in a drawer for a year going to help me? I don't think so because I think I'm still going to regret stuff afterward. And I think all I'm doing is trying to get to some level of certainty about it that I can't possibly ever achieve, which I think is in general our problem is decision makers anyway. So at some point you got to go, okay, like I know that I have to set this in stone. It is an a living breathing document, and it's gonna go out into the world. And for years from now, I'm gonna go back and say, there's a result in thinking about that doesn't replicate.

It partially replicates. Some of it replicates and some of it doesn't. So I wish I had waited, I think that news came out like three years ago. Sure, then I wouldn't have it in my book. But at the time, that was the knowledge that there was. And I just have to be okay with that. Yeah, I think that's right. And and provided to like if you want to do this space, like I don't imagine Joyce

Carol Oates puts the book in a drawer and then does not work for a year. She goes and works on something else. Yeah. Right. So so if what you're really staggering is the publishing process, you know, I think I can buy it with the the the final part of it. But if you're always working, I think that's what matters. But anyways, this is all somewhat of a jygrression from from the book, which I really liked. And I wanted to start with something when we talk about quitting. I know you're like, you don't like some of the euphemisms or different words for quitting, which I get. But it is interesting, specifically, like if we're talking about poker or we're talking about sports,

you're playing, it's a series of finite games, right? So folding is quitting, but it's not the same as getting up and leaving the table, right? And so- Well, it's getting up and leaving the hand. Right, but with the assumption that you are staying at the table, right? So like, I think a lot of people see quitting as this permanent conclusive thing when really some of the most important things to quit could also be described as like tactical retreats or folding or whatever. That there it like I think one of the reason, I guess what I'm saying is one of the reasons I think we have this aversion to quitting, which central to the book is wide, we think

this is such a bad word, is that we think we fail to make the distinction between sort of holistic quitting and quitting a specific game that you're or hand that you're likely not to or that you're unlikely to win. Oh gosh, I've brings up so many thoughts. Yes. So I first of all, I agree. So let me say first of all that I, well, no, sorry, I said first of all, I agree. So not first of all next. But second, second, let me say that the holistic quitting actually leaving the game also should not have a negative connotation. Because when you do that when the time is right, that gets you to where you want to go faster, which is counterintuitive, but it's true. And I'm sure that we'll get into that.

It's also how you would leave with your winnings intact, potentially. Well, it is how you would, or leave in a situation where yeah, you're taking a loss, but now you're not going to continue to put more money into the situation, or in the case of like a relationship or a job or a project or a product or whatever, that you're not putting more time or attention,

really valuable resources into something that isn't worth your time. And it's actually preventing you. It's blocking you from being able to put it into things that are worth your time. But to your point, I guess we're on third now. To your point, those things are all quitting when you do it within some sort of broader project.

So I don't know about you, but like, there's all sorts of stuff in my writing that I quit. I, there were at least two completely written out narratives that were in the proposal that sold the book quit that did not end up in the actual book. And it wasn't because they weren't good narratives. I actually think they're really good narratives, and they were fun, and I think that I wrote them very well. Just in the end, when I sort of looked at the book, and where they adding enough to it,

no, were there other narratives that were better? Sure. Did I need to tighten the book? Yes, all those things that cause you to dump things. And in fact, I think that you can't write a great book without lots of quitting. You have to, you have to be throwing stuff out all the time. You write things all the time that you have to just sort of let go of. And so that, that is also quitting. So I think that that's something that we also need to real. Excuse me. That's something that we also need to realize is that

there's also a quitting that we kind of don't see. Yes. Which I think is just incredibly important to understanding the endeavor itself. What does it mean to be walking away from things and not walking away from things? And it doesn't just have to be the broader goal. And then the last thing I would say is like, I think that you can get kind of infinite almost in terms of what is your broader goal. So we think about the broader goal is, is like, say to finish the book. And then we would make the distinction between deciding

that this isn't the book for me. And I know I've gotten part way through it, but I'm just gonna dump it, right, which would be sort of your view of like holistic quitting versus internal to that, you know, throwing out a chapter or maybe some section of a chapter or something like that. But I think that that's actually kind of the wrong way

to think about it. And this is where I think poker really can help us, which is when I was playing poker, we had a saying among some of the elite players that poker's one long game, that folding in a particular hand matters very little or quitting or losing in a particular game. So that would be what you would call sort of the holistic thing.

Matters very little. What matters is that over your lifetime, that you're playing this game, that you're making sure that you're betting your money as much as possible in a situation that's what we call positive expected value, where you're going to earn money. You're getting a positive return on investment. I assume that that's true for like, why do you write books? There's some goal that you have that's much longer than any single book that you might write that you're trying to achieve. Let's call it

happiness or fulfillment or and part of that might be expressed for you through communicating these ideas that you think are going to make other people's lives better. And that's something that's going to occur over your whole lifetime. It doesn't have anything to do with one particular book, or one particular podcast, or anything, you know, that kind of thing. And I think that we need to start thinking in that way a little bit more so that we can be okay with letting things go. No, you're right. I mean, you talk obviously about getting to the outside of things. And Right, I mean, you talk obviously about getting to the outside of things and it can feel like when you are quitting something, the more inside of it you are, the harder it is to quit. The bigger your view, the more zoomed out you are.

If you're seeing this as a hand inside of a game or a game inside of a weekend of games or a game inside of a career of games, then you have more perspective, you're actually freer and more able to fold or quit what should be folded and what should be quit. Then you are, if you are too much on the inside or too up close with the specific thing in front of you and then you're feeling all the inhibitions and doubts and you know biases that make it hard for you to

To take a loss Yeah, so you know, I think that said that word that you just said loss. I think it's so important in terms of really Understanding the context around this quitting problem. Sure. So Richard Thaler author of Nudge, Novel Laureate, he's done some really cool work on what's called mental accounting. So when we start something, we open up a mental account for it.

So like the simplest way to think about it is, if you buy a stock, you have something on an actual physical ledger, right? But you also have opened up a mental account. So here's the thing I've started. It's now on my mental ledger. And as you start that, that could either be winning or losing, right? So we would call that being in the gains or in the losses, meaning if I buy a stock, then I buy it at 15, it goes to 40, I have not sold it yet, right? I'm carrying this loss now. But I haven't lost past 10s. I'm just in the losses, I'm in a state of having a loss on paper. in a state of having a loss on paper. And that's also true when we have a project that's failing or we have a goal we have yet to achieve, right?

So we set some sort of goal and we're short of the goal we're in the losses. Now, if you continue with what you're doing, if I hold the stock or I keep heading toward that finish line, I keep trying to achieve that goal that I have yet to achieve. Maybe I can turn it around. So maybe I don't actually have to lose, even though I've got this loss that I'm carrying

in the mental account. Maybe I can actually wipe that off with my mental books. But if I quit, if I sell the stock, if I shut the project down, if I throw the book out the window, whatever, that's the moment where I go from being in the losses to having lost. It's the moment where I go from in a state of failing to reach my goal, to having failed to reach my goal.

That's where I realized first unrealized gains or losses. Exactly. That's where it was. Realized first unrealized gains or losses. Exactly. That's exactly right. And man, that is a powerful force. Because the line, I think the best line of anybody that I talk to comes from Richard Thaler, who said, quite simply, we don't like to close mental accounts in the losses. And what we have to realize is that being in the losses is a cognitive phenomenon, not an actual phenomenon. So I can give you an example. If you're trying to run a marathon, the goal is 26.2 miles. If you run 16 miles of that marathon and you quit, you have gained 16 miles.

Okay. So that's the reality is you've gained 16 miles, but the cognitive state is in the losses because You're in the losses cognitively. So this is like this really huge force, this really big problem of not wanting to convert losses on paper and to realize losses. And because it's a cognitive phenomenon, it's not even rational what it, like that you're losing or winning. It's just how are we processing? How are we like feeling that feel, you know?

Right. No, that is funny, right? Because even in stocks, like, to realize a gain, you have to quit, right? Like, you have to call it. You have to say, this is the end of the road for me, which is, I think, in some ways, I actually have less trouble, like calling it on something that's gone down.

I go, that thesis was wrong or I don't have the patience to stick with that. I was talking to David Rubinstein, the investor that founded the Carlow Group to the day. And we were talking about this. It's like you know objectively that most investors make most of their money by not selling things, by holding them on for a really long time. But the tension is, you know, when are you being greedy? When do you say, hey, tripling my money on something

is plenty for me. It's still difficult to quit even when you're ahead as the expression goes, right? Because you're realizing a gain, but in realizing that game, you're still, there's still the mental accounting of, well, what if it continues to go up and then I look like an idiot?

Yeah, so what's interesting, so this is very interesting. So you're unusual because the science is actually quite strong that we like to quit when we're ahead. Yeah. And in fact, that that advice is terrible Because the science is actually quite strong that we like to quit when we're ahead. And in fact, that that advice is terrible because it's amplifying a bias that we already have. So let me explain.

And this is what you're struggling with also. You're struggling with it in a different way that the average person does. But here's the problem that we have is that if we were perfectly objective, I'm a non-munition being. Yes. Then what I would do is stick to things that are worthwhile and quit things that aren't. That's what I would do.

But it's hard to know. Yes. So if I hold a stock and it's gone up, does it mean it's still going to go up? Well, I mean, we're making some educated guesses at this. We're having to do some forecasting in order to figure that out. Same thing on the way down.

So we have these silly churistics like quit while you're ahead. It turns out that those are quite bad because they make you lose sight of number one, that it's really a question of what's called expected value, which is just, do you have, are you expecting a positive return or a negative return over time? But it's also playing into a particular bias we have, which is we like to quit when we're ahead and do it too fast.

And we hate to quit when we're behind, and we do that too slow. So there's a fun study that was done by Colin Cameron and some colleagues, including Richard Thaler, actually, on New York City cab drivers. And this is before Uber. So they were looking at trip sheets from the 1980s,

long before Uber. And so the way that cab drivers work is most of them don't own their own medallion. So the medallion is just like the licensing, they cost a lot of money. It's hard to own a cab in New York City. Because the medallions, I don't know if they still do because of Uber, but at the time, it was very expensive to have a lot of money. It's hard to own a cab in New York City. Yeah. Because the medallions, I don't know if they still do because of Uber, but at the time,

it was very expensive to have a medallion. Right. So what you would do, so Ryan, you're a cab driver, you rent the cab for 12 hours at a time. That was the way that it worked. You couldn't rent it for six. You had to rent it 12 hours at a time. Okay, so you're renting that medallion,

and now you go out and drive. And camera looks at all of these trip sheets and he finds something really interesting, which is that when the drivers are getting a lot of fares, they quit really fast, right? Because you don't, you don't get the cab and drive the whole 12 hours. You get to choose how long you drive, but they quit really fast when they get lots of fares. And when they're not getting a lot of fares, when the fares are slow, they're staying in the cab for like ever. Yeah. Okay, so that, that's weird. So what was going on with

that question, question mark, what was going on with that? And what he found from talking to the drivers was that the drivers had sat like a finish line, right? Like we talked about what does it mean to be in the lobsters or in the gains. They said a finish line, which was an earning goal for the day. So they've an earning goal. So let's say it was they want to make $300 that day. So as soon as they hit $300 now they're in the gains, they're done. Yeah. Right? Like, they made it. And they quit.

But as long as they're short of that $300, they like kept going in the cab. Yeah. Now, a perfectly rational human would say, oh, if there's lots of fares, I should keep driving. Right. Because that's what I'm going to make the most money. And if there are no fares, this isn't worth my time anymore. As you said, like, my thesis was wrong, whatever I should. Yeah. I'm just going to get gonna make the most money. And if there are no fairs, this isn't worth my time anymore. As you said, like my thesis was wrong, whatever I should.

I'm just gonna get out of the cab now. And had the drivers done that, they would have made 15% more than they were actually making. Said, with there, I just wanna hit my earnings goal, which then causes me to not wanna quit when I'm in the losses, right? Not wanna quit when I haven't reached my goal. And what was amazing about how completely backwards

this strategy was, is that had they just been random, I'm just going to drive six hours a day. Yeah. Come what may? They would have made 8% more than they actually were. Sure. Having a hard and fast rule. Just a hard and fast rule, like I'm just going to drive six hours.

Like not even try to figure out or there are enough people around for me to keep driving. They would have made 8% more. Now, I assume that their whole point of driving a cab is they want to maximize their wealth, right? They're trying to make money and you can see what they were costing themselves with this sort of quit while you're ahead, stick when you're behind. Kind of bias, right? And you can see this with retail investors. They have something called the take gain order, which is like, they'll say in advance, they'll say, I'm buying the stock at 50. If it goes to 65, I'm going to sell it. They canceled them and sell it at 58, right? Like, they never actually get to the number that they're supposed to stop out at because as long as they haven't sold it, those winnings could get wiped away.

Right. And we don't like that, right? So we want to take those gains on paper and turn them into realize gain. Meanwhile, on the flip side, just like the cab drivers, they also can have a stop loss order. I buy it at 50 if it gets to 40, I'm going to sell. They cancel those too, but not to sell early. They cancel them to hold on and keep gambling. Because again, it's sort of reversed.

As long as they keep gambling, maybe they can wipe those losses off the books. Which they really want to do. They can make a comeback. They can make a comeback, exactly. And this is, I mean, this is where you can really see this like miscalibration between perseverance and walking

away where when things are going good, we want to walk away because we don't want to risk things turning the other way. But when things are going bad, we keep the risk on. We want to keep going. Even though the world is giving us really strong signals that, hey, maybe your thesis is wrong and you shouldn't keep, hey, there's no fairs around. Maybe you should just get out of your cab and go have a hot dog. Right. Right.

Yeah. Not only could they potentially made more money, but they would have spent less time idly sitting in the car. They could have spent time with their family. They could have done. They could have productively used that time to do something else. Right. Which is the problem of opportunity cost. So I think that this is something that we lose sight of. Like when you talked about being in it,

which you talk about like being in the decision not being able to get outside of the decision, this is part of the problem, which you just brought up, is when you're sitting in that cab and you're like, but I need to get to $300. What you lose sight of is what it's costing you. Yes. Which is not just like, I'm idling in my cab board

not finding anyone to pick up, but it's what could you be using that time for? And that's a thing that we need to realize. Like if you're sticking in a job, because even though it's making you miserable, because you think that grit is the same thing as character, right? And somehow you would be like weak will, or whatever, because you think that grit is the same thing as character, right? And somehow you would be like weak will, or you know, whatever, because you were walking away from something that was making you miserable.

The problem is you forget that you would be walking towards something, and the thing you might be walking toward would actually be a lot better. And so sticking has the associated cost of not just the misery that you're feeling in that horrible job, but also all the happiness you could be gaining from other things you might be doing, which by the way might not even be another job, as you said, it might just be like time with your family. In your giving up on all of those things that because your attention is a limited resource, then you can't you can only be focused on so many things at once.

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versus their leading competitors. LinkedIn jobs will help you find the candidates you want to talk to faster. You can post your job for free at LinkedIn.com slash dough that's LinkedIn.com slash dough to post your job for free terms and conditions. Apply. Yeah, no, no, that's right. And you were, you were mentioning writing earlier about sort of quitting, you know, sort of avenues

you've gone down. To me, that ties into one of the greatest pieces of writing advice that's ever been said, which is kill your darlings, right? Like you have to, just because you spend a lot of time on something, just because it's working pretty well, just because it satisfies you, something in you personally,

doesn't mean it should actually be there for the opportunity cost we talked about for the sort of ranking impact. But it's just extremely hard to quit things, to walk away from them, because I think we feel like you're losing something that you'll never get back a moment, words, time, whatever. It just tugs at us in a very special place. Yeah, so I think, think with the writing example, there's two problems here, there's actually three. So the first is just a simple sunk cost issue.

So sunk cost is simply, you put stuff into something and you're afraid that you'll waste those if you don't continue. So it's this problem where we take into account what's happened in the past in terms of gains or losses in deciding whether it's wise to continue to go forward. So I sort of talk about it in relation to fear of waste. Well, if I quit now, then I'll have wasted it all the time that I've put into this. Yes. But of course, waste isn't really a backward looking problem.

It's a forward looking problem. Does it make sense for me to continue? And one of the most char-breaking, I think, examples of this problem of fear of waste or sunk cost actually came from talking to General Tony Thomas, who was a general in Afghanistan. And he talked about talking to Goldstar mothers, who would, you know, say like, you need to go out and keep at this war and win this war so that my child won't have died in vain.

Yeah. And what he said was it was so hard to remind yourself that what mattered was if the next child that you put into war, if their life is worth the risk, right? That sadly, the casualty has already occurred. And to bring that into your decision making about whether you want to risk another casualty is not actually the right way to think about it, right? It should be, in all things we should think, would I start this today?

Would it be worthwhile for me to start it today? But what we show is once you've incurred some losses, you aren't able to think about it that way because you want to get your stuff back. You want to make it worth your time. So that's like that sun cost problem, which of course is big in what you're talking about, kill your darlings because you spend a lot of time and effort trying to write whatever it is that you've written. Then the other problem is that you're the creator. So you have an endowment problem, meaning just ownership. And we love things we

own better than things we don't. And it's really hard for us to give up things we own. We don't like to quit them, which is another issue. And then the other thing is identity is that we don't like to walk away from who we are. So you have all of these things making it really, really hard for you to be able to dump stuff, particularly when you've created them. It creates a whole other issue,

particularly when it's part of who you are. It's just really hard to walk away from things in those cases. I remember when I, and we may have talked about this before, but I remember when I was at American Apparel, the company had been around for a long time, but it was unusual and that it had this sort of CEO, creative director, model slash owner in DevCharnie, who was flawed in many ways. But in this particular area, his flaw was highlighted, and that,

you know, any fashion business, you're gonna make a certain number of things that just don't work. Nobody likes them. You're gonna make a certain number of things that people like, they're popular, so you make more of them, and then you make too many of them,

and then people stop liking them. So the point is, after a certain, the longer you're in business, the more sort of just dead stock inventory you're gonna accumulate. And you can only dump so much of this through your outlet chains or discounting or whatever. At a certain point, you just have it.

And it's just a raw cost, not simply in what you spent making it, but in storage. And so the unusual problem, like, I don't know if you remember a couple of years ago, there's that controversy with Abancronme and Fitch where the CEO was just like, give the clothes to homeless people. He was being quite ruthless and insensitive

about quitting the stuff, but Dove, like he's sweat and blood and loved all these things. And so, you know, stuff wouldn't sell. Then he'd walk around the warehouse and fall back in love, like narcissistically, like with his own creations. And try to, he'd be like, I think we can make this work. And he'd try to put it back in the stores or he would be reluctant to, to, to discount them.

And I remember at one point, I was like, you have so much stuff, the, this company's literally choking on them. I think if we just put them all in the parking lot and lit them on fire, the pure spectacle of it would be a more profitable use of the materials. Then this delusion, this inability, this delusion that they're gonna come back with this inability to quit them.

And I think about that all the time, it's not just, hey, you didn't quit this one thing. And that's a problem, but you look at a stock market portfolio, like you could have all the positions that you're ahead in. And then you could have the whole bottom half of your portfolio, the stuff that's in the red that you have refused to quit, that by the way, had you quit six months ago, a year ago, five years ago, you could have reinvested in the winners and made more money. And it becomes this thing where the more, as you said, the more your identity is attached to it, the more you have personally spent or been invested in it, the harder it is for you to walk away. And part of the reason

to have staff and teams is you want people weighing in who are less emotionally invested in you because as a result, they're less irrational than you are about it. Yeah. So I think one of my favorite stories about this particular problem that you're talking about, like you have this investment and as you're pointing out, like every time you put that back in the store, that space you can't put something new. And if it's all painted in one of the rare house, and you're falling into a full room, you're shipping back in fourth at Cosmoney.

Yeah. And and because you've fallen back in love with it, it's stopping you from creating new stuff. Like, there's just so many blockers happening there. So this, so this is like my, this was the most mind blowing thing that I discovered in my research. And I don't, you'll have to tell me if you're, you're blown away by this as well. So you're, I'm sure you're familiar with Sears. Yeah. Okay. So Sears retail company kind of has become the butt of a lot of jokes, but was a hugely successful retail company. It was, it was founded in the late 1800s, started off as a catalog business. It was called the Book of Burgans, 512 pages. You could literally buy a house by catalog.

And it was at the time that the mail service was just starting to really get underway. And there were all sorts of people in rural areas that didn't have access to goods that people had in cities. And so it was a way to connect America to goods. It was a huge, I mean, it was just really, really profitable business. I think in the 20s was when it went public and seers,

I think he personally, at that point, was worth $26 million in the 1920s. So I mean, so then we roll around to when cars start to become really popular. And obviously cars are connecting people. and they sort of see their business fault or a little so they realize, oh, people are driving places and so we'll create physical locations to sell the stuff that we would normally have in our catalog. And so they start creating physical locations, which is the way that I think about sears, and that's hugely successful. And by the 1950s, Sears represents 1% of the GNP of the United States. Think about that. That's like your head explodes when you think about that. But then obviously, eventually you get the K-Marts and the Wal-Mart by the 90s, you have target sort of at the bottom end that start to squeeze

sears out and then you have from the top end like the Neumann Marcuses and the Nordstroms. And sears just sort of loses its place in the retail ecosystem. And we know it goes bankrupt. And that bankruptcy included sometime in the 2000s, they merged with K-Mirt, which I think the financial news called the double suicide. I mean, it was really, it was bad. Okay, so that's the story that everybody knows about Sears.

But to your point about like this ownership over stuff and how that can really create all these problems, there's a whole nother story about Sears that I didn't know until I did the research for the book, which was that Sears was not just a retail company, it was also a financial services company. So that started in the late 1800s because they had to offer credit to their customers. And then, remember I said they built these retail locations because of cars. So someone had the brilliant idea in the 30s that, oh, well, people have cars and they need to ensure them. So we should offer them insurance. So we'll do that in our stores.

And they found it a company called Allstate Insurance. In the 1930s, which now is the biggest and personal liability in sure that there, I mean, I think the market, I'm not sure, I'd have to double check, but I think the market cap of all states like 40 billion dollars. Okay, so they owned all state they found it all state they owned it. Um, roll around to the 70s and like the credit business is doing really well so they they they found the discover card. Yeah, right. Okay, they buy Dean Whitter, which was a big stock broker firm. Yeah. And they also acquire Coldwold Banker, which is a real estate company.

Yeah. Okay. All right. So now you have to wonder, because all state, I think, is like a $40 billion company. Dean Whitter discover Morgan Stanley bought it. And at the time, it's unclear exactly how much it would have been worth today, but at the time, it was 40% of Morgan Stanley's value. Okay, Morgan Stanley was worth a lot of money, so I don't know. And then they ended up spinning off Discover. And I think

Cole of Banker merged with some other real estate companies became Reology and it's market cap, I think it's $2.2 billion. So we're talking about Bethany and some billions and billions of dollars worth of market cap. I think it's $2.2 billion. So we're talking about billions and billions and billions of dollars worth of market cap. So your question might be, wait, I'm so confused like why is Sears broke? Yeah. That doesn't make any sense.

Well, because when the retail business started to falter, which is their identity, that's what Sears is, right? When it starts to falter, the shareholders start to lose their minds. Because they're like, what's going on? Like the retail business is losing money. Like you need to do something about this. And the board made the decision to quote unquote, get back to its retailing roots.

And so in order to save the retail business, they sold off all the- The genesis of the actual businesses. They just sold off all the- The genocents, the actual businesses. They just sold them all. Yeah, right. And then went broke. And from the outside looking in, you're like, this is nutty.

This doesn't make any sense, like why on earth would you do it? And it's because they had a warehouse full of clothes that they had created. Right. And they didn't want to send it out into the parking lot and light it on fire and continue on with all stayed in Dean, Witter and Discover Card and all of that stuff that was honestly making money hands over fist. And there I think it's such a good example of like that is what our failure to quit talks,

you know, does to it, particularly in the service of our identity. Because that is why seers didn't sell those things off. Because if you asked the average person on the street, what is seers, they would have said, oh, they have retail stores where they sell stuff. Right. Yeah, to be to become who you are, you have to stop being all the things that you don't need to be anymore. And this is true not just from a business standpoint, but you have to leave different parts of your life behind, different parts of your identity behind

to grow up and mature and change into what the moment before you requires. That's exactly right. And you know, the hardest thing to quit is who you are. Yeah. And that's not just true of things that we're pursuing. It's also true of our ideas. And I think that this is something that's so important for people to understand is that, and you can see in a, you can see in a Sears story

is that we have the intuition as individuals that once we start something, because when we start things, there's lots of uncertainty. We know very little, there's going to be luck involved. We've all had that feeling of like, oh, if I knew then what I knew now, I would make a different decision. Well, that's that feeling of the uncertainty of starting an endeavor or even forming a belief, right? And then after the fact you find out new stuff, and what we think is, oh, when I find out that new stuff, then I'll change my mind.

I mean, obviously, I'm a normal human, right? If things are going really badly, if I'm climbing up Everest and a snow story comes in, I'm gonna stop climbing. If I'm running a marathon and I break my leg, I'm obviously gonna start running, right? If my retail business is losing money hand over fist, and I've got this other stuff

of obviously going to sell the retail business, and this is the thing that we need to understand is that that intuition is just wrong. When we get information after we've started something that it's not going well, it's not just that we don't walk away, we like double down on it. And this is true of our beliefs as well.

So I think like we're all super frustrated by the political environment that we're living in now where there's all these people who are holding these beliefs and you're like, hey, the facts on the ground, just don't match up with what your beliefs are and you're sitting there scratching your head saying why aren't they willing to give these up? And the answer is because we don't, because those beliefs are part of their identity. And this is the really disturbing part. So it's for the same reason you wear clothes that aren't in style anymore, or you have a haircut that's not in style anymore. Wait, are you safe? I'm thinking about my hair.

No, it's true, right? Because it's who you are. like you see people with, you know, where it's like, oh, you're like 15 years behind. Yeah. And this is the thing to really understand about this particular problem is that the more extreme the beliefs you have, the more this is a problem. So if I believe something that's completely mainstream, that everybody else believes, like, you know, Neptune is whatever this many did, you know, whatever it's, you know, something about, well Pluto, like Pluto is a planet. Okay. So then everybody thinks that and then someone comes and says, no, they're whatever they called it, like, you know,

asteroid the permanently. It's a, it's a pseudo planet. And then I go, oh, okay, I guess I was wrong because everybody believes this. I'm not, I don't believe something that's different than other people believe. So when we think about this problem of identity, right? It's like, I just, it's not really that Pluto's a planet that doesn't really have anything to do with my identity. But when I believe something that is outside of the mainstream,

that's when my beliefs can get really wrapped up in it. So, and this is true for everybody. So I'll give you a more extreme case of it and then a pretty simple case of it. So Leon Festinger, I'm sure you're familiar with Festinger's work at like one prophecy fails. So he did, there was a, there was a doom stakeholder called the Seekers that

was found by a woman named Mary and Keach. She believed that aliens from the planet Clarion were going to come. This was in the 50s and white bus all off the face of the earth with a flood, but people in the cult were the true believers were going to get rescued by the aliens on midnight of like December 20th of that year right before the aliens came. So you know, simple doomsday cult stuff. So anyway, fasting or just saw a piece in the paper about this and said, oh, this will be really interesting

because the thing about a doomsday cult is they actually have a doomsday. They say, why not? There's a date. There's a date. So this is going to be for sure disconfirmed. And so I'm just going to go join the cult and see what happens.

So he did with some colleagues. He joined the cult. And they're all sitting there the night that the aliens are supposed to come. And of course, they don't come. And you know what happened, they didn't quit the Colt. Not only did they just move the date. They, well, they moved the date. They thought they were going to come later. They thought maybe they had believed hard enough that, that like now the aliens had given them some respite or something like that. But they actually, and it wasn't even that, it was like people who were sort of mild

in their beliefs became very much even stronger in their beliefs. So this is a good example of like, oh, geez, even though they said a date that someone was going to be reinstated into something, and then the date comes and it doesn't happen, why do people still believe in it? Well, okay, here we go. Like this happens. But it's not just happening to like cult members. So John Bersier's and Katie Milkman looked at stock analyst predictions of earnings. And what they found was that let's say that we're both stock analysts Ryan. And we both like all of us sort of have the same estimate of earnings for a particular company. And then when the actual earnings come out,

it just really conflicts with what our prediction was. But we all had the same, you know, we all were sort of in the same zone. We then will update our prediction for the next quarter. Okay, so we all agree, we get new information, it disagrees with what we thought was true, and then we all change our belief. But, Ryan, if you make an estimate that's out of the mainstream, that's really different than what everybody else is saying, and then the earnings come in, and it conflicts with

your forecast, you don't abandon it now. You actually double down on it. You believe more strongly in it, And the amazing thing is you get financially punished for it, but it doesn't matter. You won't give it up because when you stand out from the pack, it's more of part of your identity, that belief that you have. And then, you know, all this information that can come in that completely disagrees with what you believe. And you're like, yeah, you just rationalize it away. Well, to go to your point about politics,

I think this is the thing we're struggling with is we keep expecting once we show these people enough information, though, change your mind. And what we fail to empathize with, and I realize it's difficult to empathize with it when you, when things are what they are. But the amount of guilt that you are asking these people to voluntarily accept by admitting they're wrong

is essentially superhuman. The cognitive dissonance isn't just this quirk of the mind. It is a, it's a warm blanket that, you know, the reason you don't wanna accept that you were misled by a cult is that you would feel stupid and nobody likes to feel stupid. But nobody wants to feel like the bad guy on top of feeling stupid, right? People don't like to admit they've been conned. But what if in the process of being conned, they were part of a vicious, racist, anti-Semitic,

anti-American, you know, regressive movement, you know, that's a tall order to ask a person to accept, right? When we ourselves don't like to admit that we are lost on a, you know, a driving trip with our family, people are just not gonna do that. And that's the tragedy of, I think the situation we've slowly backed ourselves into. Yeah, I mean, a bit of a depression, but no, I completely agree. And I mean, if you think about just the people who were in the seekers, they had

abandoned their families. They gave over their worldly goods. Yeah. You know, so when the facts on the ground come in conflict with those types of beliefs, it creates tremendous discomfort. That's really what cognitive dissonance means. There's only two ways to resolve that discomfort. One is to change your belief. One is to rationalize it away. To your point, you've abandoned your family. You've probably heard the people that you love, you know, you're given all your stuff away.

I mean, there's just all this stuff that's happened. Yeah. And, you know, obviously, what that means is that, you know, when it's a choice between the facts and your belief, your belief is gonna win there, and you're gonna rationalize it away. And as you said, we think it's like, oh, there's some sort of character

flaw in these people that they want to ban in the police. But you don't admit your loss, right? Like stock analysts who have every incentive in the world to get it right will just like cling to these really extreme predictions that they've made because they stand out from the crowd. And when we're talking about, you know, in today's politics, the situations that you're talking about, these are people who are really doing something that's against the mainstream, right? Like they're really, they're really standing out from the crowd in a crowd while they're doing it, but they're standing out from the crowd. And, um, Bob, you know, and that's incredibly hard to let go.

So, you know, one of the things, I mean, kind of speaking to the top of your last book, is that I think the thing that we really need to realize is we think that perseverance is the courageous thing. Yeah. And sometimes, right? Like sometimes you're sticking to things that are really freaking hard, but are totally worthwhile. And the fact that you're conquering the dragon is actually heroic, that is courageous.

But we need to recognize that quitting is a really courageous act. Because you have to walk away from all this stuff. You have to take the loss. You have to say the thing that I believed was wrong. You have to say, I failed. I'm lost. I didn't get it right. Like, these things are all so incredibly hard for us to do. And I don't, I think that we think of quitting as so cowardly. But it's the opposite of cowardly. It's courageous when it's done at the right time.

I think that's right, and especially when it depends on what's on the line, right? So like in discipline, I tell a story of Shackleton, you know, he's sort of by endurance, we conquer, he's not quitting because there's people on the other side of the obstacle that he's trying to rescue. And that's different, like persevering to save someone is different than persevering with a bad idea that you want to be vindicated, right? And so I think a lot of it comes down to stakes. We often raise the stakes on things that don't matter,

and lower the stakes when they really do matter. And then we wonder why our quitting versus sticking, you know, sort of choices are all out of whack. I mean, I think the shackled example is really good, because this is where we can see the contrast. If there are people on the other side that you wanna rescue, then perseverance really makes sense.

But if those people are with you, and you're continuing past the point at which it's clear that you're putting their life in danger, then you're ought to be quitting. And what I think is so interesting about that is very often our rationalization for continuing because we don't wanna stop short of the goal. He had a goal, the goal.

Right. If you don't get there, you're done. Sure. One of our rationalizations is, I owe it to all of these people who have come with me and put in all of this time and effort to do this. I owe it to them to keep going. And it's like, no, but the moment that you realize that the chance of them dying is way too high for what they signed up for, you actually owe it to them to turn around. And this is something that I think

Stewart Butterfield, who founded Slack, explained to me, I think in a way that was super clear because it was a similar problem that he had when he was thinking about shutting down the endeavor right before Slack. So that was a company called Glitch. Is it a video game, right? Or somebody? Yeah, he was developing one of these like online multiplayer world building cooperative games, which was a critic starling, by the way. It was really, people loved it.

But he determined at some point before anybody else could see it, that it wasn't going to, it wasn't going gonna be a success. And he had a moment where he was really struggling with, you know, but my poor employees, do I owe it to them? This is something that Ron Conway, who founded SV Angel, also talks about. But what he realized is, if I've realized that this isn't gonna be a success,

and my employees are working for very little cash comp and mainly for equity because of what the promise of what that equity is worth, then the minute that I've realized that that equity isn't worth their time, then I owe it to them to shut it down. Because otherwise they're continuing to work for something that I already know isn't worth it. So that's like a lower stakes version of the sort of this hypothetical shackleton. If he's continuing in a situation where he has now determined that this, you know, the chance of success is too low. And the chance of death is too high. Then to continue in the service of saying,

I owe it to the people who have come with me to try to get there. That's actually a backward way of thinking about it, which is different than trying to go rescue people, which I agree with you, you should try to go do that. I had a podcast I was supposed to do. I wouldn't say who it was, but I was a podcast I was supposed to do in person. I'd flown all was, but I was a podcast I was supposed to do in person. I'd flown all the way out to L.A. to do it.

And she was, she was like feeling sick, you know, and she was like, I'm not feeling good. I don't think it's COVID, you know, she's like, I'm a blah, blah. You know, she's trying to make all the, and I was like, just fucking cancel it. I was like, it's not a big deal. Like, let's just cancel it. And she was like, you know, thank you. It's so hard for me to do this. Like, when I, and I was like, if we all quit stuff, when we weren't feeling well, a little bit better,

we probably wouldn't have just been through this horrendous pandemic, where I'm knowing people done. You should, like, I think if you are, I forget who I said it, but there, some description of some politician where they said, even his retreats were always done, or as a general, even his retreats were always done with or as a general, even his retreats were always done with the assumption of a later advance. If you can sort of wrap your identity, if you can put at the core of your identity, I'm someone who can lose the battle in order to win the war, it puts you in a position where you can cancel these little things or even big things, but that are little and perspective of the larger things, as opposed

to being almost so fragile that you have to have this rule that you never quit anything for any reason. And as a result, you ultimately harm yourself and other people. If you're just like, I'm always in the big scheme of things moving forward, it allows you to take steps back, sideways, et cetera. To me, that's the balance that I think you want to get to. Yeah, I mean, I think that brings us to the, you know, back to what we were talking about at the beginning, which is what is the broader endeavor, right? Like you have to quit a lot of stuff along the way to think about what the broader endeavor is.

I think somebody told me, I'm gonna probably get this wrong, but it was something like Washington, who we think of as like one of the greatest generals ever. I think he fought something like 11 battles and he only won five of them. Or it was something like that, or 12 battles, and one of the other. It was really good at retreating.

That was actually his greatest great. He was like, he was like, he was was actually his his he just was a huge mungus quitter. Yes. Because again, what he realized is like, look at his situation. Now, he has a really limited resource, right? Like, we have the smaller army. We're not as well armed. We have less on ammunition, you know, so on, so forth. And so being really judicious about when is it okay to continue on? And when is it not? Because that lift to fight another day is like incredibly important. And you know, this is the thing that we really need to realize is that we think that quitting stops our progress. Yeah. Like dead in our tracks, that's what we think it does. But it actually speeds us up. It actually gets us to where we want to go faster.

Because if continuing to fight that battle is going to use, you know, our infantry, it's going to use our ammunition that we have a limited supply of in a situation which isn't worthwhile. That is a humongous waste. Retreat, save that stuff so that you can get yourself into a better position and you can use that more wisely. And that's not just true like of infantry and munitions. It's true of your time. And one of the favorite things that I, you know, from talking to people in the book,

were on Conway who I mentioned before, who's the founder of SV Angel, he's got this saying that now, like, I just try to like wrap into my soul, just life's too short. And he says this all the time, like life's too short to spend time on something that isn't worthwhile because that's time you can't get back, you can't go spend it on things that are worthwhile. And I think to your point, it's like we don't realize it because we have, we worship at the altar of grit and like perseverance and that means character and all of this stuff that the easier choice is often to stick to it. Usually harder to walk away from things. It's sort of figuring out what is required to win

or succeed in the thing that you're in in with the resources that you have. So to build on your Washington point, the pivotal moment in the American Civil War is Ulysses S. Grant realizes, I have superior resources. I have more men. I control the territory that I need to control. So if I don't quit the North winds and Robert E. Lee fails to realize that he has less men, less resources, doesn't control all the territory than it needs to control.

And he doesn't realize that every time he wins, he's actually losing. Right. And that grant, so it's this tension where Grant just realizes, hey, every time we fight, even if we fight only to a draw, I win. And even if I lose, I win, right? And Lee sort of so obsessed with winning the individual battles, fails to see the larger picture of the war. And so they keep just clashing into each other over and over and over again.

And he doesn't, it's like he doesn't notice that his army is getting smaller and smaller and closer and further and further away from the North each time that he does this. And so I think it's fundamentally realizing like what game am I playing? What do I need to have or do to win this game? And then you quit the things that are preventing you from doing that, and you stick with the things that are helping you do that. That's really the sort of calculation

that you have to figure out with anything, even with a book. It's like, I'm not quitting the book, but I am quitting every dead end inside the book. And then that allows you to ultimately, if you just don't walk away from the thing, eventually you'll get to the outcome that you have set out for yourself. Yeah, and I think what's important is sometimes you do quit the book also, right? And hopefully you figure that out fast. That's the thing that you want to do.

So, you know, look, what you're talking about is what's so important is that it's rules of thumb here are bad, right? It's not like, oh, quit everything or stick to everything, which is actually what the rule of thumb is, right? Like, quitters never win, owners never quit. Like, if it first you don't succeed, try try again. And to your point about about Lee, no, if at first you don't succeed, sometimes it's because it's not worth succeeding

and you should go rethink. Right? Don't just keep going. But, you know, that's the rule of thumb is stick to it. That's going to create success. But rules of thumb here on either side of the equation. I wouldn't want someone to overcorrect it. I'm just going to quit everything. It's about calibration. When is it right to stick to things? When is it right to walk away? And that has to do with, is the path that I'm on worthwhile? Is it actually helping me to gain ground toward what my goals are in a broad sense. And that's really where the trick is

in distinguishing between those two things, which is really nuanced. And the problem is it doesn't fit on a coffee cup. Right. It's not so. That's really the issue is that you're asking someone to to, you know, you're asking someone to do some work and trying to think about it. And I think that that's just hard. I think it's hard for everybody. It's hard for me, right? I like the aphorisms. It makes, it makes my life easy.

It reduces my cognitive load. And isn't that easier for me? The, the, the Truman aphor, or I mean, sorry, the Churchill aphorism of never, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever, ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever ever whole thing and why it's such an advanced elite level thing to figure out even though quitting seems so simple and straightforward and anyone can do it. Yeah, and I think the problem is that we see is with that Churchill quote, everybody forgets a second half. Yes.

We don't think about it. So, you know, this is, this is the thing is that it stick to things in less. I mean, and that's what you need is that unless, what's the unless mean? Right? So he says, you know, obviously, Churchill has an opinion about although he doesn't give details, but that's fine because at least he's adding an unless to it. This is the thing that we need to remember is that I think that we believe that goals are just universally good. Right? Particularly in today's age of like, okay, ours and whatnot.

It's like, okay, set really clear goals and that's going to send somebody on their way toward that goal and then I'll be right with the world because they're going to get there really fast. And the answer to, you know, the problem with that is, yes, that's true. Goals are definitely motivating. I mean, the science is very, very clear on this. Goals will motivate you towards something and you're more likely to achieve that day

if you have a goal. The problem is to the point of Churchill is that you have to have an unless because goals otherwise are very inflexible. Yes. They become sort of fixed objects and they're fixed objects that are graded as pass fail. Meaning progress along the way matters very little. What matters is did you actually get to the

finish line and that's it. And that's how you end up with people heading toward things where they don't want to quit for fear of quitting, you know quitting short of the goal. And this is not just a problem for me as an individual, like I have a goal like to close the sale, right? That's gonna keep me pursuing leads that I shouldn't be pursuing because it's very clear that the customer is never gonna buy. And now I'm failing to go and like pursue other leads that might be more fruitful.

That's a problem for me personally, but it's also a problem from a leadership perspective because people are judging you just on whether did you hit the goal or not. And they're not rewarding you when you do abandon a lead. You're just getting like the, you know, you're just, it's like you're going into a post-mortem afterwards and being told to defend yourself against,

hey, I decided that this wasn't worth pursuing anymore. And that's just for like a single lead in sales. Like, what if you're pursuing a project or developing a product or whatever? Like, we just judge people like, do you hit the goal or not? Yeah, and again, like progress along the way doesn't matter. And then you end up with people like Shavano T.

running the 2019 marathon, who literally broke her leg on mile eight and kept going. And so, you know, the medical personnel were like, stop running. You're going to do pertinent damage to yourself. And she finished the marathon. And the thing that's weird about her is she's not unusual. There were four people in that same marathon who kept running with something broken. And it happens in every single marathon because there's a finish line. Yeah. And that's why we need to be actually more like Churchill,

not the never ever ever give up part, but the except part. No, it's like we have so much trouble motivating people to do something like running a marathon that we feel reluctant to brand the person who needlessly finishes it on a broken leg as insane and unhealthy. We don't want it. We don't want it to take away. Let's be serious. We all kind of admire her. Yeah, right. Like to be honest, right? We shouldn't. We should. We should be a caught. That should be as cautionary a tale as a drug addiction or any other kind

of, you know, thing taken way, way, way too far. I mean, I talked about this in the new book. It's like, if you're a disciplined person, naturally, or you've been rewarded for your discipline, the hardest thing in the world is to be disciplined about your discipline. Because it's easier just to let it run a much, just be like, whatever, whatever the hard thing is, I'm going to do that thing and I'll drop dead before I stop. And it's like, okay, then you're going to drop death. And the thing is that it's like a dad going back to this idea of like, what really is courageous? Yeah. We all can intuit that there's going to be an article written about what a badass she is for having run 18 miles on a broken leg.

Never mind that I assume that she loves to run. And she was putting herself at risk of never being able to run a marathon again, but of lengthening her recovery time of all these things for one single marathon, like who cares, it's like a single hand of poker, right? Like, go stop, go heal, run another thing. Don't put yourself in a position where you may never run again.

But we all know, we can intuit that. Right? Everybody's going to be like, what a badass. She's a hero. That really took courage. And the opposite is, you know, cowardice, I guess, or whatever. No, no, if she quits, first of all, if she quits with the broken leg on my late, there's nothing ever it's going to be written about or nobody's ever going to. Yeah, we don't even know that it happened. We don't even know what happened.

Not audible. Right? Or if it's just that she's running and she says, you know what, I was starting to feel some really bad pain in my leg, so I quit. We'd be like, really? What's wrong with you? You're a marathon runner, right?

You're such a whoosh. And I think we all know that. You might have caught it before the leg broke. Well, she started, she started actually sealing some pretty excruciating pain in my myel-3. And it wasn't until like myel-8 that she broke her leg. So there you go, like she probably should equip before that. But you know, but if she did that, it's like, everyone's gonna be like, well, why'd you quit it? Like, what's wrong with you? You quit at myel-3. Oh, you're experiencing a little pain. What do you think a marathon is about? And so when it comes down to this choice between quitting

and not quitting, it's actually in a lot of ways the easier paths to keep going. Because you know people are gonna pat you on the back and tell you that's so amazing that you're doing something hard and you're so incredible. And when you quit, you were like, why are you such a loser?

And part of what happens is not just like, externally what we think, but we also carry that internal narrative. And in the end, I think that, you know, what that causes, this is something Richard Taylor told me also, which I think was so good, is that we're we're usually not willing to quit until it's no longer a choice. So what did it mean by that? Like until it's so incredibly obvious. So like, maybe if Shivano Keefe, if by continuing to run it turned into a compound fracture, and there was actually a bone sticking out of her skin.

Like then maybe she would have quit. Because you know what? Nobody will question that. We're no good reason to say why'd you go there. You know, you want someone to make the decision for you. Yes. And sometimes the world, it's not somebody but like the world makes that decision for you. So like, you know, and Ron Conway, when he's working with the people that he invest in, he's an angel investor, he's trying to get them to see that it's failing. Before there

is no choice, in other words, before they're trying to raise their next round, and there just isn't any money there. So they've run through all the money that they have, all the capital they have, and then they can't raise another round. He's trying to get them to see that before then, right? And you know, there's these stories of mountain climbing, obviously, where people are climbing into snowstorms, and it isn't until there's no visibility, and they have no oxygen,

and somebody just literally died right next to them, and then they're gonna turn around, because nobody's gonna question that decision. And the most important nobody questioning that decision there is you, you don't have to live with the what ifs, what if I continued, maybe I could have made it. And so we wanna butt up against the situation where there is no choice anymore. But then it's like, first of all, you're already like 95% dead at that point, if not 100%.

You're in the crevasse. And also, the time to quit when it was like if we were omniscient would have been long before that. And all of that time that you kept going just to get to absolute 100% certainty that you were supposed to quit. Again, it's time that you could have spent doing other things that are so much more worthwhile. Right. Right. Yeah. No, there's still the sunk cost. Like you're going to quit regardless. So you might as well quit sooner than later. Yeah. And this is so there's there's somebody that I talked to for the book, I just adore is Astroteller. And Astroteller is the CEO of X at Google,

which is the innovation hub. His actual title is Captain of Moon Shots. And so, you know, the charter for X is 10X better in five to 10 years. So they're trying to create these world-changing innovations in a relatively short period of time, but even Google has limited resources. So she's really thinking really deeply about as we go into developing an innovation, which is going to carry with it a really high degree of uncertainty.

So you're going to have a lot of information discovery after the fact. How do we figure out as quickly as possible to reduce those costs, right? How do we figure out as quickly as possible, whether this is something to continue or something to walk away from? And he has a mental model that I just like totally love, which is called monkeys and pedestals that he uses to do this. like totally love, which is called monkeys and pedestals. They use this to do this. So imagine that you need to make some money. I don't know, maybe the book business isn't going so well

for you, Ryan. So you're like, you know what I'm going to do? I'm going to train a monkey to juggle flaming torches while standing on a pedestal in the town square. And that's going to be your money making scheme. His point, Astral Teller's point is, if you're gonna do that, you need to figure out if you can train the monkey

while juggling flaming torches before you build the pedestal. And the reason is that you already know you can build the pedestal. Right. Like, you can do it, it's gonna feel like you made progress, but it's false progress. It's the illusion of progress because you have you've learned nothing new about the endeavor.

The thing that you have to figure out is can you actually get this monkey to juggle flaming torches? And if you start there, if you start with the hard thing first, there's all sorts of good things that come out of it. Number one is you can figure out if you can unlock the system or not, right? Like before you ever spend anything else and you're going to get to the heart of the matter like really fast. And then you're going to reduce your sunk costs by not building pedestals that don't matter. And once you sort of know that mental model, you realize the absurdity of people going

into projects. And what do they always say? What's the low hanging fruit? And then they go off and do that. And it's like no, no, no, no, no. The low-hanging fruit or pedestals, you already know you can do them. It's not that eventually you don't have to take care of the low-hanging fruit. You should never do that until you've figured out whether you can train that monkey or not. And on their presentations, they actually have things like hashtag monkey. And one of the thing that I love, and I wish that this had happened before, this is going back to choice Carol Oates, I wish this had happened so I could have put it in the book, is one thing that I have in the book

is that X considering building a hyperloop. So a hyperloop is supposed to be like really high speed fast trains, like through like some sort of pneumonic tube or something on track. It's going to get people like super fast to where they want to go. And so they actually considered it at X developing that. And so they identified the monkeys and they felt that there were kind of two monkeys. Monkey number one was, can you get people on and off the train safely? So can you get it up to speed in a way that doesn't kill people? Can you stop in a way that doesn't kill people? That was monkey number one. We need to solve that problem. And then monkey number

two was just really stuff like regulatory problems, because you're going to be going through all sorts of different areas and there's a billion different regulatory issues associated with each locality and would you actually be able to solve that in a way that would allow you to build the whole thing. And as Astroteller said, we're Peter Pans with PhDs like we're not we don't know about regulations and that was going to be really hard. We don't know about regulations and that was going to be really hard. So they sort what they figured out in terms of the first monkey was that in order to be able to answer that question about can we stop and start safely, that they would have to get it up to full speed. And in order to get it up to full speed, you would have to basically build the whole thing before you actually figured out whether you could solve for that monkey.

So they said, this is not for us. We don't want to have to build the whole thing in order to get our answer. That is not an X project. And so they abandoned it. And because they had the mental model, they, it took them 15 minutes. They considered the project for 15 minutes before they said, no. Now what's interesting is some other people have decided to develop that that and what they just discovered was exactly what he saw. So there was an article in the New York Times just recently about the hyperloop and what they said was they only were managed to build enough

track to get it up to about a sixth of the speed and they sort of considered that proofful concept which of course it wasn't. And then now they were budding up against all of these regulatory problems after they had dumped like so much money into the project. And if they had just done what X did, maybe that wouldn't have happened to them. So I think it's like such a good example

of he figured out to quit in 15 minutes. Now this is years and years later of development of the hyperloop, and exactly the problems that if you thought about monkeys and pedestals, you know, are sitting there right in front of you, they're now just budding up against after years, and you know, millions of dollars invested in the cause.

Now I love that. It's one of my rules. Do the hard thing first. Yep. Always, which is why I write a proposal, by the way. Of course, no, if you can't figure out how to crack the book. If you can't figure out what the book is, you shouldn't start the book because you're unlikely to figure that out as you go. Right, so actually, when I was talking to Nikki at Portfolio

about this book, having already done two books with her, I was generally telling her about the idea. This was early in my research process. And she said, oh, well, you should just come pitch that. Don't write a proposal for it, we love it. And I was the one who said, oh, no, no, no, no, no. And I went and wrote, I think that proposal was somewhere around 60 pages or something like that. Because I realized that the hardest thing is like, can you, it's not obvious, even though it feels like it's

not obvious that when you come up with an idea, like, Oh, I'm going to write a book about quitting that there's a book there. Or what the order that you should put the book in or what the concepts are that would support it or how you want to communicate it or any of those things. And I hardly wanted to be like four chapters in and figure out that I couldn't figure out the book. So I went out and wrote a proposal. I took two months from the first conversation I had with her, went off her at the proposal and then we went from there because because exactly, the proposal is actually,

I don't know about you, but I think writing the proposal is much harder than writing the book. What's to go to your point, it's because you're training a bunch of different monkeys. You're solving all the difficult problems. And then the actual writing of the book is still a problem.

Is that easy to build a pedestal? But once you've figured out what it is that you want to say and that there is to say, figuring out the best way in the most interesting way to say it is not that difficult comparatively to figuring out if there's something there in the first place. Yeah, yeah, that's, I mean, yeah.

So, yeah, exactly. So all of that stuff, you know, it's all those monkeys and then you go to write the book and you're like trying to build the most beautiful pedestal you've ever seen. Sure. But it's all pedestals at that point. Totally, totally.

And, and yes, once you know that the pedestals not going to be for not, you can do a better job. That's right. You're not simultaneously trying to do this other difficult thing. Yeah. And I think to Astarteller's point, it's like, if we think about all these issues of identity and work product and ownership and sunk cost and whatnot, what he recognizes, it's going

to be a lot easier to dump a proposal than it's going to be to dump a book. And it's going back to that issue of waste. You know, he says there's projects where there's projects where they're $2 million in before they figure out they can't tackle the monkey. It takes that much to figure out that you can't unlock the hard problem. But from his point of view, that's not a waste because what he realizes is if they weren't thinking about it this way, it might be $9 million before they figured out to set the thing down.

So it's not a waste of $2 million. It's a savings of $2 million. It's a savings of $7 million. And I think that we have to just sort of rethink things in that way. And understand, look, the faster you figure it out, the better off you are. And the easier it is to move on to something else that's going to be a much better use of your time. Well said. Annie, this was amazing. As always, I love the book. Well, thank you. I'm so happy that you love the book. I'm so appreciative that you were willing to blurb it and read an early copy of it. And also, I love your new book, which I also got to read early and blurb as well.

Yes, thank you. I love that we have books coming out right, right near each other. You'll be faster with your next one than me, no doubt. But I'm going to try to be, you know, at least half as productive as you are. I think that would be a goal for everybody. Well, I'm going to go try to work on the next one now. OK, all right, awesome. All right, I'll see you. All right, bye. To me, discipline is the most important trait a person can have, right?

It's not knowing what you should do, it's being able to do it, right? To have the force of will and character to stick to the right path, and even, as Seneca says, when those around you are hopelessly lost. There's no one truly great that we truly admire, who hasn't been defined by their self-control and their discipline. So I can't wait for you to check out the new book discipline is Destiny the Power of Self-Control. The second in my four virtues series on the Cardinal virtues of Stoicism courage discipline justice wisdom the new book is out now we're still honoring some of the pre-order bonuses which you can grab at dailystoke.com slash pre-order but you can pick up discipline is destiny the power of self control anywhere books

are sold grab it on audible you can grab it on Kindle you can pick it up at your local indie bookstore if you want me to sign your, you can pick it up at your local indie bookstore. If you want me to sign your copy, you can also do that at dailystilic.com slash pre-order. And we even have some signed manuscript pages for people who order five copies, plus you get a bunch of other bonuses, which I'd love to give you. So sign up at dailystilic.com slash discipline. Hey, prime members, you can listen to the Daily Stoic early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free with Wondery Plus in Apple Podcasts.