The Daily Stoic - How Regret Can Propel You Forward | Daniel Pink (PT. 2)

Episode Date: April 12, 2025

In today’s Part 2 episode, award-winning author Daniel Pink joins Ryan to explore how fear of regret, awkwardness, and failure hold us back—and how embracing a 'shots on goal' mindset can be life-changing. Dan opens up about how he reframed a personal regret to shape his future choices, while Ryan shares what he sees as his own version of the infamous 'No Ragrets' tattoo.Daniel Pink is an award-winning author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human. Follow Daniel on Instagram and X @DanielPinkSign up for Daniel’s newsletter The Pink Report: https://www.danpink.com/📕 Grab signed copies of The Power of Regret by Daniel Pink at The Painted Porch: https://www.thepaintedporch.com/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to The Daily Stoic early and ad free right now. Just join Wondery Plus in the Wondery app or on Apple Podcast. We bet you didn't know. Our new quieter trains are great for listening to that self-help podcast you lied about actually listening to. Get on board. Via Rail. Love the way. Get on board. Via Rail. Love the way. Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview stoic philosophers. We explore at length how these stoic ideas can be applied to

our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. You know, my first book was very different than my other books, right? Welcome to another episode of the Daily Stoic Podcast. You know, my first book was very different than my other books, right?

I wrote Trust Me I'm Lying, which is sort of expose of the media system. And a question I get a lot from people is, do I regret it? Like, do I regret not so much writing the book, because I'm proud of that, but do I regret the things that went into the book? Like some of the people that I worked for, my line of work, some of my choices. And I always struggle with that question because regret's not the right word.

I would do it differently, right? But I also understand that who I am would not be possible without that. Now, maybe if I've killed someone or if I've done something profoundly immoral or wrong, I might have a stronger feeling about this. Like who I am would not be worth what I had to do. But I feel shaped and informed and changed by that stuff, largely for the positive. And, you know, I mean, it wasn't without consequence for myself or other people. There's certainly things that I feel like

I've had to make amends for. There's certainly things I, again, wish had gone differently, but I tried to do what Seneca did, which is make a good ending of it. So I like where I've ended up. So regret is an interesting topic. And so I was excited to have Dan Pink on the podcast. He was in town for a conference

and he came out to the studio. We had a lovely conversation. He's got this book about regret. It's called The Power of Regret, How Looking Backwards Moves Us Forward. One of the things we talked about in the episode, if you listen to part one, he was saying that when he travels,

he likes to pop his head in McDonald's and in other countries and see what they're like. And right after we talked, I was in Abu Dhabi and I went to this mall to get some toys for my kids. I wanted to grab them something cool. I found this Toys R Us in a mall in Abu Dhabi and I walked by this McDonald's and I took a picture of it, which I ended up showing my kids.

They were fascinated by it. Like they had like a cake counter, like cakes and donuts and all this stuff. The McCafe section was actually very impressive. But it's funny, from this conversation, I took the time to poke my head in there and look at it, it was interesting. And then literally like minutes later,

I'm flipping through the New York Times and there's an article and the headline was Fries with Your McBaggett. For some travelers, McDonald's is a destination. And it was a review of a book that is nothing but pictures of different McDonald's around the world, which I thought was funny. So now I have to text them a picture

of this Abu Dhabi McDonald's. Anyways, part one with Dan was awesome. And if you haven't read any of Dan's books, you absolutely should. The Power of Regret, How Looking Backwards Moves Us Forward. His other books include When, A Whole New Mind, Drive, and One, I think is one of the best titled business books of all time, To Sell is Human. I think Trust Me on Lying was a great business book title, although we've had some, it's caused me some trouble over the years. If there's something

I regret, I maybe wouldn't have put Liar in the title of my first book. I maybe would have just gone with Confessions of a Media Manipulator, which was the subtitle. I've always admired to sell is human as just, not just a brilliantly chosen title, it's just a great phrase, but I can only imagine like if I was a sales manager or a CEO, I'd just be like, we gotta have this guy come talk.

That like, I just have respected as a, as like a writer speaker. This is a great idea. Anyways, this is part two of our conversation. Dan and I are talking, Regret, his writing process, lessons from whistleblowers, we went in a strange direction,

how quantity is a way to get to quality, and much more. You can grab signed copies of The Power of Regret at The Painted Port. You can follow him on Instagram and Twitter, at Daniel Pink. And I am off to Hawaii for this very brief trip that I told you about.

And I will probably be recording some episodes on my phone while I'm there. And then I will be back working, even though I'm traveling again. Like my assistant was like, okay, do you wanna go from Hawaii to here to here? And I said, no, I'm going home. I'm picking up my kids from school.

I'm dropping them off the next day. And then I'm going to the airport. And I learned that from Dan, as we talked about in part one of today's episode. I'll just get into it. Here we go. One of the things I think we underestimate, I guess, is how good our fellow human beings

are at avoiding awkward shit. So like you think, hey, if I reach out to this person I've drifted away from, we're going to have to like deal with all this stuff. And it's like, no, you'll just pick up where you left off and not know. We're really good at ignoring the elephant in the room, actually. Just do the thing and let it happen. Yeah, we also, again, going back to the idea that most people are like most people, we also don't extrapolate from our own experience. So the guidance you give to people

in this kind of situations where they say, if I say, oh, man, I can't reach out to Ryan, it's like, I've been talking for 10 years, he's not going to care. You say, well, how would you feel if Ryan reached out to you? Oh my god, that would be great. I'd be so happy. Yes.

I think that's true about asking for help. When people are like, hey, I'm really struggling or what about this? I'm never like, stop bothering me with this bullshit. And then I need something or I'm lonely or whatever. I'm like, I don't want to bother anyone. I'm actually excited. It's so out of the ordinary when other people do it. You're like, I can't believe you came to me. What can I do? And then you're like, I really, I can't bother anyone with this shit. Yeah, this is why to my kids and to every person, the is I counsel them to ask other people for advice.

Yes. Always ask people for advice. Yes. People love giving advice. They love giving advice, especially the younger you are, and especially if you're a student of some kind, you have special status, you you're a student of some kind. You have special status. You have like a VIP pass,

use it as much as possible, because it does go away. And it's not that people won't give you advice when you're older, but like they are uniquely inclined to help you at the phase of life that you're in right now, you should take advantage of it. I actually think there's also power in advice,

older people asking younger people for advice. Yes. Because of the surprise. It's kind of, I've been waiting for reverse mentoring to be a bigger thing than it is. It should be a bigger thing. You know what's funny about speaking up though? Cause I've talked to a number of whistleblowers over the years. Like I interviewed, and not whistleblowers, but also just people who spoke up.

Like I interviewed Kinzinger and Tyler Schultz, the Theranos guy. And like, I won't say they regret it, but like we tend to celebrate whistleblowers after we put them through a fucking wringer and it was the worst, most miserable experience of their life. They don't regret it, but there is something about like we celebrate speaking up, we make movies about them, and then we glide over the fact that it costs them hundreds of thousands of dollars in legal bills, and we questioned their integrity,

and blew up their private life, and didn't believe them. I get why people convince themselves not to do it. We don't make it easy. No, no. But you also, if you think about, let's take, is it Tyler or Taylor Schultz? I can't remember. Tyler Schultz.

OK, let's take Tyler Schultz as an example. If you compare, would you rather, would he have rather gone through that hell versus not going through the hell and avoiding everything altogether? OK, probably. But would he have rather gone through that hell? That's not the comparison.

The comparison is going through that hell and then living through that mendacity and not saying anything. And I think that it's not like between going through that hell and like having a charmed life. Of course you would want that, but that's not the option on the table. It's basically you have these two things.

So you have to ask yourself compared to what? I mean, think about what people think about him versus now what they think about his grandfather. Yeah, right. Although when your parents are mortgaging their house to pay for your legal bills, because you pointed out an obvious and horrendous fraud, I can see why other people are like,

I don't know if it's worth it or not. Absolutely. And that's kind of what they, which by the way is what that response is supposed to engender. And it's also, but also to me, this is why we should celebrate the people who are with the lowest. Of course.

Because they're willing to, they're willing to surmount that cost. Yeah, yeah, yeah. I interviewed Alexander Vindman. Wow, wow. Just imagine you're just like, you have to take on the most powerful person in the world. And then people are like, oh, you're just doing it for the money or whatever.

And you're like, what are you talking about? But that's what we do. In the short term, we question the integrity of the people that later on we celebrate and make into sort of exemplars. And so it's rough. So how do you make decisions? Do you make decisions for the short-term comfort or for the long-term benefit?

Yeah, I think that's a really important thing you've got to think about when you're wondering about if you're going to regret it or not. It might be a pain in the ass for you to show up to work at 9 o'clock tomorrow morning, but you do it because it's less comfortable in the short-term but a bigger contribution in the long-term. Do you think that's a practice you can build?

Like you can develop the muscle of doing, like those sort of delayed gratification things? I think that you can build, I mean, my view as a writer has always been that structure is liberating. I am a big believer in structure of any kind. So for instance, I mean, this is not anything new. I think what I, my practice, whatever it is,

is very similar to other people's. But if I waited until I was inspired to write, I'd never write a word. But that's not what I do. What I do is when I have a writing project is I go into my office, I'm a little bit more diligent than you are going at 8.30. So I go in-

What time zone, what time zone? Eastern time zone. So that's actually 7.30 your time. So I'm way ahead of you. I got an hour and a half lead. I know. So I go into my office at the same time and I give myself a word count.

And I don't do anything until I hit that word count. I don't bring my phone with me ever into the office. I don't check my email. I don't watch sports highlights. I just give myself a word count wherever I am in a particular project. And I don't do anything until I hit my word count. And some days it happens relatively quickly,

other days it's excruciating. But I don't do anything until I hit that number. Yeah, I think there's a great quote about how inspiration is for amateurs. Yeah, totally. Yeah, yeah, yeah. It was, I think the person who said it was Chuck Close. Yes.

But yeah, he has some problems. Oh, is he a problematic guy? He's a problematic, he turned out to be a more problematic guy than we would hope for someone of that talent. Doesn't seem that hard. To be a decent human being? Yeah.

I know, I know. I mean, I guess we all have skeletons, but it seems like not that hard to have, to not do it. Yeah. Yeah. So that's what I do. And then I do it the next day. Yeah. And then I do it the next day. Yeah. And I do it the next day. And I do it the next day. And then the pages pile up. But if I waited until I felt like doing it, it would be excruciating. I mean, the other line adjacent to that is the Julius Irving line, Dr. J, who said, being a professional is doing what you love to do,

even on the days you don't feel like doing it. Yeah. Yeah. To me, that's what writing is. I treat writing as like building a brick wall. You lay a few bricks every day, make them stand up straight, do it every day, and eventually you have a wall.

You don't have a wall in one day or four days or three weeks, but you have a wall eventually. No, if you show up every day, eventually- Well, I'm not sure building a wall is the best metaphor right now. His book was an unpenetrable wall of texts also. Have you ever wondered how a circus performer could become the most powerful woman

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Follow Even The Royals on the Wondery app or wherever you get your podcasts. You can listen to Even The Royals early and ad-free by joining Wondery Plus. Every big moment starts with a big dream. But what happens when that big dream turns out to be a big flop? From Wondery and Atwill Media, I'm Misha Brown, and this is The Big Flop. Every week, comedians join me to chronicle the biggest flubs, fails, and blunders of all time, like Quibi. It's kind of like when you give yourself your own nickname and you try to get other people to do it.

And the 2019 movie adaptation of Cats. Like, if I'm watching the dancing and I'm noticing the feet aren't touching the ground, there's something wrong with the movie. Find out what happens when massive hype turns into major fiasco. Enjoy The Big Flop on the Wondery app or wherever you get your podcasts. You can listen to The Big Flop early and ad-free on Wondery Plus. Get started with your free trial at Wondery.com slash plus. If you show up a bunch of days in a row, you will have an editable product on the other side of that.

It might not be publishable, but it will be editable. It will exist. And that is the first step in not existing, is making it exist. Something beats nothing. Yeah. Forward, not static. Yeah. Are you going to have something good? No, not necessarily.

Are you going to have something? Yes. And something beats nothing. And you need something to get to good something. And then for me, there's always, there's a moment, I was just working on something literally yesterday where I was so frustrated and it crossed the sucks to doesn't suck border. And that's an exhilarating moment.

It's like, okay, this thing, it sucked for a while and now it doesn't suck. Is it great? No, but we've made that progress going forward. And it was probably impossible to get there without the phase of sucking. Like it needed to be in the disjointed. You needed to do that.

You needed to get the work. You know, people have different styles. There's some writers I know who can just crank out stuff really quickly and pretty elegantly quite fast. That is not me. That is absolutely not me. For me, it is a grind every single time.

I'm just grinding this stuff out. But when I grind the stuff out, I then make it better. And then I make it even better than that and make it better than that and make it better than that until it's decent. Yeah, Austin, Cleon has this thing about being the verb, not the noun. Which is, like doing

the thing is different than, you know, assuming the identity of the thing. And so if you're writing, eventually you can be publishing. Writers write. Writers write. Yes. Yeah. Because that's what you do. Because that's your job and you show up and you do your job. Yes.

Even on the days you don't feel like it, especially on the days you don't feel like it. And that can be a lot of the days. I would say it's the majority on the days you don't feel like it, especially on the days you don't feel like it. And that can be a lot of the days. I would say it's the majority of the days. Yeah, I would say you have more good days than bad days. Or sorry, more bad days than good days. Totally. And so to me, actually having a good physical practice is- What do you mean by physical practice?

Like running or weightlifting or I bike or I, you know, some hobby where that is also true. And you have experience and you have developed the muscle of always being glad you have done it, but you didn't always enjoy starting doing. Like I went swimming with, I swam in Barton Springs. I was, I don't know, 48 when I got in the water or something. And the water was not 48, but it was 40.

Even though I do it all the time, I love it. I think it's one of the wonders of the earth, this pool here in Austin. I did not enjoy starting. No. I didn't enjoy getting out either, but the second half of the swim I really enjoyed. And then once I got to my office and I warmed up,

I was glad I had done it. Absolutely. And that as a metaphor for writing and for most things in your life is a really valuable one to have understood. Amen. Yeah, and I think there's a muscle. There's a muscle of getting in a cold plunge.

There's a muscle of sitting down and writing. Like just the doing shit you don't wanna do muscle. I agree with that. I think the, yeah. Now I also think that it's important to choose the shit you don't want to do. That is rather than have it handed to you. Yes. So if you have a job that you hate where you're getting assignments that you hate,

and, um, I think that can be, I think that can be debilitating. Yeah. Someone told me that. But for whatever reason, like, but if I say I want to write a book or I want to write an article about X, Y or Z, it's going to be hard. And so show up and show up and do the work. Yeah, someone told me that about parenting where it's like, you know, your kid wants to quit the piano. It's not whether they're quitting the piano or not. It's whether they chose the piano or not. So if they want to quit the piano and you were forcing them to play the piano, they should be allowed to quit. If they begged and pled and told you this whole story about how they

really wanted to play the piano, quitting then has some implications or larger life lessons. You should want to quit your homework. It's been forced on you. Listen, I wrote a book about this a long time ago. Human beings are self, I think that the human beings at their core are self-determined. They are autonomous. And that when we're, our natural state, the natural state of kids and the natural state of adults before it gets beaten out of them

is to be autonomous and self-directed. Yeah, so if you wanna quit a job that you hate, that's a powerful signal. It's either something really worth doing that you have to power through, or it's the wrong thing for you to be doing. And you've got to have- And that's not always obvious.

I think you really have to interrogate that. You really have to question that. Yeah, and it could be true for a while. It could be true. It could be one thing for a while and then another thing. Just because you did something and it was good. Like, it must be hard as an athlete, right? Because nobody really likes practicing, it's hard.

Every season is a grind you have to work. But at some point it stops being the thing you should be doing. And how do you know, is it just the normal grind that you're pushing through to get into the season that you're then glad you did? And then how do you know like, this is the last season for me?

Those are similar feelings, but with very different implications. Or how do you know when your body's saying, hey, you're a little sore today, but push through, and then you'll loosen up, and you're about to blow out your knee. And that muscle, if you only have the willpower muscle and never the question and the willpower to

quit muscle, you're going to get yourself in trouble. I mean, Annie Duke has a good book about quitting, you know, and I do think that in some ways powering through, sticking with it is slightly overrated. But it's, this is what adult life is about. It's about making these kinds of decisions about when to stick it out and when to quit. And we don't always know. I think what's useful is when we make that decision, whether it works out for us or not,

is taking some time to reflect on it, to talk to people about it, to see what you can extract from it. Yeah, what I liked about her book is the distinction. And poker is a good analogy for this is that you know, you're quitting a hand. Yeah. That's different than quitting a game. Exactly. And then quitting a game is different than quitting playing poker. Exactly. And so there's different levels of retiring from the field.

Exactly. Exactly. So it's possible that I could quit early on a day on a writing day. Yeah. That's different from quitting a book. Exactly. So it's possible that I could quit early on a day, on a writing day. Yeah. That's different from quitting a book. Yeah. And it's different from quitting being a writer. Yeah. Now at this point, I'm poised to do all three, but that's another story. Writing is a tough one because it's one of the few arts you not only can do longer, but it is not out of the ordinary for someone to do their best work towards the end. There's a lot of there's actually a lot of there's actually a decent amount of research on that issue.

It's something that, you know, the older I get, the more I start thinking about. So you have somebody like Philip Roth, who said also problematic. I've exactly but he incredibly talented and problematic, who said, I'm done. Yeah. He could have continued writing books. I think he probably could have gotten another book deal. And he said, I'm done. Now, what you also see is some really, really interesting work.

So there's this guy named David Galenson at Chicago, University of Chicago, who's an economist. And he looked to see whether, he looked to see at what age people, artists, visual artists, and others poets as well, made their breakthrough work. And his he has this very simple and straightforward view of creative capabilities. So some people are are conceptual innovators, some people are experimental innovators. So some people make a big breakthrough, sort of a paradigm shifting breakthrough.

And that's how they create. And other people sort of experiment with different things and eventually make a breakthrough. And so the conceptual innovators, they make their breakthroughs at a very young age. And then the experimental innovators, they take a long time before they do their best work. So an example from the world of art would be somebody like Andy Warhol. So, Andy Warhol is a crazy dude. I would really

recommend Blake Gopnik's massive biography of Andy Warhol. It's a fascinating book. I mean, it's an incredibly detailed book, but it's a fascinating book. But the gist of it for Andy Warhol is, Andy Warhol did his best work, his legendary work, work that now sells for tens if not hundreds of millions of dollars, basically in 1962. Almost all of it was from this moment where he said he was a commercial illustrator, commercial designer, and he started doing some wacky things.

And in this very short time, when he was young, he had this big breakthrough. And the stuff they did later on, not as significant in art history, not even close. Then you have somebody like Mondrian, who was painting trees, like realistic images of trees. And then he said, wait a second, maybe I should be painting, and he did that for a while.

And then he said, oh, maybe I should be painting branches. And so he started painting branches. And he says, well, actually these lines are kind of cool on these branches. And he didn't do his legendary work until much later because he was experimenting with his way in there. So according to Galenson, those are two different ways of doing things.

So some people make their breakthroughs late in life based on how they do things. Other people make it early in life. And he has this theory, it's true in poetry, it's true in the visual arts, it's true in certain sciences. Now, that said, that might be right. I wrote a piece about him a long time ago. I think it might be right. I think it's very interesting. There's other research showing that, which I think is even more interesting, is that when you look at, say, like scientific

breakthroughs and you map out, let's make it, maybe you have like a, you have a chart, all right? You have a chart and you look at, and the X axis is age, and you start plotting where people, at what age people had their breakthroughs. It's clustered very much toward the young, right? Yes. Usually unmarried before they have kids. You have, hold on, hold on. So that's, I think that's right. Okay. So it's clustered very much toward the young. Yes. And then usually unmarried before they have kids. You have a hold on, hold on. So I think that's right. OK.

So it's clustered toward the younger ages. And then there are some people sprinkled out over here. And what this guy Barbasi at Northeastern figured out was that, yes, it mapped to age. But what was driving it was an age. If you actually adjust for how much they produced, it evens out. That it was basically the reason that people were doing more innovative, getting their breakthroughs earlier in life is that they were taking many more shots on goal.

When they were younger. Exactly. They were taking, and so if you adjust for essentially shots on goal, age doesn't really matter. Interesting. It's all about shots on goal, age doesn't really matter. Interesting. It's all about shots on goal. I also wonder if it's weighted by like prodigies, right? So you have... Yeah, maybe. I mean, like a John Nash, you know, but... Well, no, there's a, I read this interesting book a couple of years ago called Boys Among Men, which is about the generation, which now you can't do, generation of NBA basketball players

that went straight from high school. Right. Because now you have to, so there was a, but there was a brief period where you could. And so you had this generation of guys, LeBron being one, Kobe being another Kevin Garnett, where it wasn't so much age, it was that their, it was that their amount of years playing perfectly intersecting with the peak physical capacity.

So instead of, so it's like having, let's say it takes three years to get the hang of being an NBA player. Do you want to start that at 17 or do you want to start that at 21? Well, if you started at 17, your physical peak and your understanding. So that, like I got lucky as a writer

in that I dropped out of college. And I sold my first book at 23, I think. So like, I think I got lucky in that I got my hours in a period of time that might have been dead time for someone else. I think that's possible. I mean, it's also, it's why good college players who maybe go to the transfer portal

or play until they're 20 through 24 years old, don't get drafted in the NBA because they're too old. Because they've missed that window. For the rest of us where it's less of the physical capacity, I think there's a very strong argument for shots on goal as one of the best predictors. Yes, quantity is a way to get to quality, an underrated way to get to quality.

And it also takes into account the randomness of success. That is, if you only take a few shots, then randomness, if you take a lot of shots, there's going to be probably a normal distribution. You're going to have some big misses, you're going to have some big hits, and you're going to have a lot of stuff in the middle. But if you take only one or two shots, it could fall anywhere in that distribution. You're going to have some big misses, you're going to have some big hits, and you're going to have a lot of stuff in the middle. But if you take only one or two shots, it could fall anywhere in that distribution. And so, you're not taking advantage of that. You're also not taking into account how fickle the world is and how random circumstances can take

a great work of art published in the wrong time and interpret it fundamentally differently than it actually is. You got it. So you see now, you see some artists being, you know, getting shows posthumously because someone discovers like, oh my God, they really were great. And you know, you see that with some number of, you see that to some extent with the, some of the women who were abstract expressionists back in the day who were getting drowned out by the loud mouths like Pollock and de Kooning and so forth.

But the takeaway for me is shots on goal. Yeah, don't be so precious. Shots on goal. Yeah, and I think it's also- And also being willing to miss those and being willing to miss those shots on goal. Well, to go to your point about self-determination, if you can, maybe you don't choose what your calling is, but if your calling is to be a movie director,

you've picked a thing where the amount of shots you have is not as much in your control as other artistic domains, right? So it's like, if you, how many $200 million, you know, films are they gonna, are you gonna be able to make in your lifetime? And if, you know, the hit rate is 20%, you know%, it's gonna be hard for you to get that distribution, to get the one where it lines up. But today, if you have the equipment that you have in the studio, you can make a whole bunch of short films

and put them out there and see what happens. And each time you, theoretically each one you make is gonna be a little bit better than the one before it. You're gonna, and it might not work. That's the thing. It might not work, but what's not gonna work, what I think you can make a pretty strong bet on probabilistically, if it's not gonna work is,

I'm gonna do one. Yeah, yeah. The work of genius I'm gonna make in my cave and be polished for the next 20 years. Yeah, I'm not sure that's a good strategy. Well, and this is also to go to your point though, about I think one of the things that can happen is if you are that scientist or artist or entrepreneur

whose first thing is enormously successful, it makes it hard for you to take more shots on goal. It should make it easier, but it can make it harder for you because you become paralyzed. Like I have a great book I'll give you in the bookstore about Harper Lee. She actually did, people think she just never had another idea.

She was gonna write a book about this murder trial in Alabama about this pastor who was murdering people for insurance money. It would have been a surreal and strange and potentially amazing book. And she just couldn't get out of her own head because in her mind, it was never gonna be to kill a mockingbird. And so there's something too about your point

about quantity or sorry, about when you even out for how many it takes. If you're that more methodical person and your first handful don't hit it out of the park, it makes it easier for you to continue doing it in a way that I think- Yeah, yeah. There actually is some, again, what's interesting now is that there are scholars out there who are studying this in large numbers and there is some evidence of that, of exactly

what you're talking about. But I mean, at the unit of one, I think that my diagnosis of Harper Lee is ego is the enemy. She was thinking too much about herself and what other people were thinking of her and not just simply doing the work and making a contribution to the world. Self-consciousness is the enemy. Self-consciousness is the enemy, awkwardness is the enemy.

And again, I keep coming back, you know, I keep coming back to these things as forecasting errors. They're forecasting errors because the truth of the matter is that this is liberating for me as a younger person, as someone who maybe earlier in my life actually seemed like I sort of cared what other people thought of me. And then I discovered what people thought of me, which is that they weren't thinking about me.

Nobody was thinking about me. And once you release that yoke, it's liberating. And so the forecasting error is that people were actually thinking about Harper Lee. They were just, I think, I really believe that you're going to take grief no matter what you do if you put anything in the public. So if you have the audacity to put a book or a work

of art or anything into the world, people are going to not like it and say they don't like it. Of course. And that's the price. But most people aren't really going to care one way or another. And most people are not going to say, ha ha ha, that book number two is in as good as book number one. Because most people don't even know you have book number one. And most people don't, most people aren't thinking that. You're thinking about that. You're thinking about that. You're thinking about that every single day. So Harper Lee made a forecasting error,

and we're paying for it because we don't get to read that cool book. Yeah, you're thinking about deathbed regrets as an artist. You're probably going to regret what you didn't publish more than what you did publish. I mean, it goes to boldness. And as people aid, we know, again, we'll come back to these regrets of inaction. But when you look at what people regret, when you look at these 26,000 regrets,

very few people say, you know what, I was like, you know, I tried to do something too innovative. Should have played it safe. Yeah, I really regret trying really hard on something that nobody had ever done before. I really regret being so innovative. No, there will be people who say that. But most people are like, I played it too safe. I didn't take enough risks. I phoned it in.

I was too scared. I didn't speak up. Yeah. I mean, it's really overwhelming. And what I was suspecting is that there would be some national and cultural differences. And at least superficially looking at these qualitative reports, there really isn't that much. If I were to show you the database, would pop up, you know, regret number 10,143. And I just read it to you. Yeah. I think you would have a very tough time telling me what's the age of the person,

what's the gender of the person, what's the gender of the person, where's the person from? I do hate that one, you know, people go, no one ever sat on their deathbed and said, I wish I worked more. And I don't know how many people are like, I wish I took way more ski vacations also.

Deathbed regrets are BS largely, I have to say that. Why is that? Because first of all, there's no systematic collection of them. We don't know what they are. We simply speculate. And we might know about one, and we say that that is universal, so we don't know that.

The other thing is that those kinds of regrets are, they're kind of too late. You know what I mean? And so to me, that regret is such a ubiquitous experience in the human condition that you actually wanna look at it way before then. Every single person, every human being, basically every human being with a functioning brain

over age five has regrets. It is one of the most common emotions that human beings have and it's there for a purpose. It's there to teach us, it's there to signal to us it's there to signal to us what matters. Yeah, and then, I mean, because I had, you know, there's things I regret in my twenties,

but people kind of want, they want you to say that you regret them, you know, which you do, but at the same time, there's this sense of like, you wouldn't be where you are without those things. So how do you think about that? Well, okay, okay, so that's, I think that's, I think that's actually an easy problem.

So, okay, so I think that's actually an easy problem. OK. OK. So you say, OK, so I'll give you an example. Go back to the database for a second. I'll give you an example from my own life. It might be better. So in my misspent youth, I went to law school. I should not have gone to law school.

That was not a good idea. And if I had it to do over again, I wouldn't go to law school. That was not a good idea. And if I had it to do over again, I wouldn't go to law school. However, I met my wife in law school. And so that ended up being one of the smartest things I've ever done. And so if you say to me, if the devil or the angel, whoever, the spirit comes down on this table here in your studio and says, all right, Pink, here we go. I got a deal for you. You can go relive your life and you don't have to go to law school. You can do something else during that time. I'm like, psych.

However, the price of that is you can't meet Jessica. I would say, Satan, no thank you. All right? And now, so can I still have that regret and learn from it? Yeah, and the regret that I learned from it is, don't be conformist, don't do what everybody else is doing, don't be so risk averse. And so you can be satisfied with where your life is

and still have regrets that you can learn from. And that probably the primary beneficiary of that regret is not you, it's a young kid who's asking you for advice, who's thinking about going to law school. So you can go, hey, it worked out for me, but you should probably not do it. Yeah, yeah.

Because it's not a foregone conclusion that you will meet your spouse at law school. I mean, the idea. That was a random. That was completely random. I mean, going to law school to find a spouse is not optimal. Yeah. All right, that is not a wise strategy.

It happened to work out for me, but it's not a wise strategy. But I do think that I can learn from it, because I can say, when I'm in a situation where I learn so much from that bad decision, so much from that bad decision, about conformity, about not taking risks, about think about, this is a huge one for me, which is thinking that I knew how something worked before actually investigating it.

So again, not to turn this into therapy of my bad decisions earlier in life. I went to law school. It's crazy. I never visited a law school. I never sat in a law school class. I never talked to a lawyer about what he or she did. That's crazy.

You don't do that. Okay. No, most lawyers hate being lawyers. And so you should talk to them. You don't do that. Okay. No, most lawyers hate being lawyers. Yeah. And so you should talk to them. You don't do that. Yeah. And so I can learn from that regret.

So I can carry that forward to other decisions that I make. This is one reason why like I have a daughter in medical school and you cannot even think about applying to medical school unless you have spent considerable amount of time shadowing physicians. And there are people who will go out saying, I want to go to medical school because I'm good at science. And they go out shadow physicians and they're like, I don't want to do this.

And that's great. That's a great thing. You know the no regrets tattoo? Have you seen that? Yeah. I have my own version of that, which is, so I have the obstacles away tattooed here as a reminder. And then I have you go as the enemy tattooed here.

And I, so I went to one parlor and got one and then a couple of years later, got the other. And I was like, just match this font, you know? And the guy was like, do you know the font? And I was like, no, but you're a tattoo artist. You know the fonts. I just matched them. And he was like, okay, I'll do my best.

And you know, they don't match and it drives me nuts. And it's not quite no regrets. There's no typos or anything on here, but it is a constant inked reminder for me of like, whenever I go, eh, you know, that I end up regretting. I regret not being more, let me slow down here and get the details right. For certain kinds of things.

Yes. For things that are permanently etched on your body, I would say that would be- For things you can't undo. Right, exactly. Or, but would say that would be- For things you can't undo. Right, exactly. Or, but also just deferring to expertise. But you can't undo that. I got a guy in the book, Jeff Bosley, who he went into the army and he got on his, he's

right-handed on his arm right here. He got the tattoo, no regrets. Yeah. Okay? Because he wanted to be tough. And then he served in the army for a while. And about six or eight years after he came back, he decided that he didn't want that tattoo anymore. So he got his no regrets tattoo removed.

Lovely. I like the tattoo. It's just to me, it's like, oh, hey, if I had taken, it's like a measure twice, cut once situation. Yeah, yeah, yeah. It's a nice vivid reminder of the costs of not doing that to me. I have no tattoos. Why not?

Do you regret it? You know, it's like, I'm like, I might be one of the few people who's completely agnostic about tattoos. Like the people that, oh, tattoos are the greatest thing in the world and other people are like, oh my God, that's so ugly, it's so horrible. I'm like, ah, I don't know. It's also a classic example of like, you know,

they say, why do people like having been in fraternities? Cause it was painful to get in the fraternity and then the cognitive dissonance, right? So, the reason you don't hear a lot of regrets about big tattoo pieces is that it was very painful to get. Yeah. And you don't want to admit you were getting it. Although tattoo removal is a pretty large industry. Now, yeah, sure. Yeah, yeah, yeah. I'm not going to get it removed to get it right back on slightly better. Right. You know, Then it's like an even more vivid example of. Now it's the opposite lesson. See, you caused yourself this pain

to get something exactly right when, by the way, I'm the only one that notices they don't quite match. Has anyone ever pointed that out to you without your rating? No, that's what I'm saying, never. So it's just, you know, so that it's, there's a golden mean there, I'm sure. Well, this was awesome. You wanna go check out some bookshelf facts? Sure, of know, there's a golden mean there, I'm sure. Well, this was awesome.

You want to go check out some bookshelf? Sure. Let's do it. Sure. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show.

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