The Daily Stoic - How Regret Can Propel You Forward | Daniel Pink (PT. 1)

Episode Date: April 9, 2025

We all experience regret, but what if we could turn it into an advantage? Best-selling author Daniel Pink joins Ryan to reveal how regret isn’t just a painful emotion—it’s a powerful tool for growth, better decision-making, and a more fulfilling life. They talk about the challenge of juggling work and family, the surprising most common regrets people have, and the eye-opening data on how regret shapes our future.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. 📕 Grab signed copies of The Power of Regret by Daniel Pink at The Painted Porch: https://www.thepaintedporch.com/Follow Daniel on Instagram and X @DanielPinkSign up for Daniel’s newsletter The Pink Report: https://www.danpink.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. I'm Raaza Jafri and in the latest season of The Spy Who, we open the file on Ewan Montague and Charles Chumley, the spy who duped Hitler. 1943. Winston Churchill wants to capture Sicily, the key to breaking Hitler. Churchill's spy chiefs devise Operation Mincemeat, one of the war's most daring deceptions, that hopes to make the enemy look in the wrong direction. The success of the plan relies on the unlikeliest of heroes,

a deceased homeless man named Glendor Michael. Glendor is given a new name, a cache of fake war plans, and is dropped into enemy waters. Montague and Chomley now wait to see if German intelligence have been fooled by their ruse. If it fails, then it could spell disaster for Europe. Follow the Spy Who on the Wanderer app or wherever you listen to podcasts. Or you can binge the full season of the Spy You Duped Hitler early and ad free with Wanderer Plus. Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength

and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their lives. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I am about to board a long flight to Hawaii from Texas. It's what like three and a half to SF and then like five or six from SF to Hawaii from Texas, it's what like three and a half to SF

and then like five or six from SF to Hawaii. It's gonna be long and it's going to be for a very short amount of time. I'm gonna be in Hawaii for less than 24 hours. Now, when I was younger, I probably would have gone and made a whole vacation of it, but this is gonna be a short trip because my kids are in school and they can't come.

And so I'm not gonna be gone very long. I'm actually gonna be in Hawaii for one night. I land in the evening, I'll have dinner, I'll go to bed, wake up the next day, do the talk, see someone, fly home. That's my thing. And actually I talk about that with today's guest because I sort of heard a rumor about him that helped inform this.

His rule is that he's never away from home for more than two nights. Like what I'd heard is like if he had two gigs in Hawaii in the same week, he would fly home in between them. If that meant not missing more time with his kids. And that's always sort of shaped how I've tried to manage my travel schedule. Not always, I've always been perfect at it,

but it's what I think about. My speaking agent knows like, the thing is bedtimes. Like getting home at 9.30 PM is the same as being gone. So how do we orient all of it around? I try not to be gone that much. Do a lot of talks, but I try not to be gone that much. And when I found out that Dan Pink, Billy Oppenheimer, who's my researcher, who I've worked with for a long time,

let me know Dan was gonna be in town for a conference. I tried to see if I could fit into his schedule, and he did. Dan's awesome. Dan's written like a bazillion New York Times bestsellers, drive to sell as human, when, a whole new mind. And then more recently, he did this book called The Power of Regret, How Looking Backwards Moves Us Forwards.

And I'm gonna split this episode in two parts because we really got into it. We talked about some pros and cons and quirks that come from being on the road, having hard and fast rules, and then his idea of regret. And I think about regret when I think about how gone I was in some of my kids' first year or two.

I regret not so much what I missed with them, although I did miss some, I mean, but they were so little. I regret what that meant for my wife, certainly. I regret what it cost me and I look at what it got me and I don't always see that trade-off. So that's how I have this rule. And look, when I have people on the podcast, I'm often trying to work through this stuff myself, and Dan is someone whose work has shaped me, has informed me.

He's just a thoughtful, interesting guy. And I think this makes for a great interview. I'm excited to have him on. And speaking of kids, I'm about to finish this up, go pick up my son from school. We're going to ride our bikes at Koda. They let you do this, you can ride your bikes on the racetrack, which I didn't know about until relatively recently,

even though I live close. And so we're gonna go have some family time before I get on this flight here. And I'm excited about that. So here is my interview with the one and only Dan Pink. He signed some copies of the Power of Regret at the Painted Porch. You can follow him on Instagram and on Twitter

at Daniel Pink. Enjoy everyone. Stoicism, the stoa in stoicism comes from the stoa pochile in ancient Greek, which is the Painted Porch. That in Stoicism comes from the Stoa pochile in ancient Greek, which is the painted porch. That's where Stoicism comes from. I did not know that. Yeah.

So Stoicism just means porches. It was a philosophy that was set up in the Athenian Agora amongst the people. Is that in Ego is the enemy? Where do I tell that story? It's not registering for me and I've read a couple of your things. I don't know if I tell it. Maybe it's in the obstacles away, but I don't know if I tell that story. It's not registering for me and I've read a couple of your things. I don't know if I tell it. Maybe it's in the obstacles away, but I don't know if I told that story in writing anywhere.

But yeah. Yeah. So basically Zeno is this Phoenician merchant. He's a merchant traveling the Mediterranean, suffers a shipwreck, washes up in Athens, has no money. He's in the Agora. And he passes a book seller and the book seller is reading the works of Socrates and he, this

is his introduction to philosophy. And he remembers as he's listening to the bookseller, he remembers a prophecy that he heard as a young man that the path to wisdom was having conversations with the dead. Okay. And then he realizes that books are conversations with the dead. That's like a very Ryan Holiday point. Yeah. Okay. And then he realizes that books are a conversation with the dead. That's like a very Ryan Holiday point. Yes. Yeah, yeah.

Like I associate that with you more than with Socrates. And then sets up a philosophy school in Niagara on the painted porch. And that's where the name comes from. Got it, got it, got it. That's where the name comes from. And the porch has a big mural on it. Now, what's your connection to this part of the,

did you just come to Austin? Just moved to Austin 12 years ago. We bought a ranch out here, so that's where we live. And this is the closest town to that ranch. Got it. Other than that, no history, other than we just really like it. Okay.

But I like living in the middle of the country for travel purposes. Sure, sure. So how long did it take for you to get to the Austin airport? 25 minutes. Oh, okay, that's not too bad. Yeah. I mean, that's about what it took me to come in here.

Yeah. My house is actually closer to the airport from here. But I actually heard an urban legend about you. I wondered if that was true. It's not true. It influenced my life, nevertheless. Did it influence it positively or negatively? Yeah, positively.

Oh, then it's true. Of course. What I heard from someone was that you speak a lot, but you never spend more than two nights away from home. That's pretty much right. Yeah. So like if you had a talk in London on Monday and a talk in London on Wednesday, you might fly home in between.

If maybe not Wednesday, but Friday, definitely. Yeah. Yeah. Yeah. Or maybe even Thursday. Yeah. I think I can't remember the exact number. I think I've gone up and back to Australia in like 36 hours or something. You did two different flights to Australia

instead of spending an extra night in Australia. Well, no, no, no. I just, instead of staying an extra night to get some rest, I just came, basically turned around and came back. Yeah. I do that. Yeah. Yeah, yeah, yeah.

But the extra nights, no, you're totally right. Now, also my kids are older now. Right. My kids are out of the house. They don't care. They don't know where the heck, I mean, I don't know if they cared then. I cared then. Yes.

Why I have young kids and so- How old are your kids? Eight and five. Oh, nice, all right, fantastic. But so I heard that before I had kids and then it kind of stuck. So I, when I talk to my speaking agent, it's not obviously fee matters and place matters,

but mostly I measure it and how many nights do I have to be gone? Absolutely. I have in my head a rough heuristic of how long I'm, at least in the past, how long I'm going to be away and how much I'm getting. There's a cost to being away, especially when, especially when your kids are that age. Yeah. I think about it, it's not even nights away, it's more bedtime. So it's like, if you tell me I can get in at 11, if I was just married or single, I'd be like, okay, I get home at 11 PM. But like 11 PM might as well be 6 AM the next morning.

Yeah, of course, yeah. What really matters is am I home by seven? I can't think about it. It's good, that was one of the few, that's mostly true and one of the few good decisions I made in the last 25 years. Is just being around for your kids? It just in general, I mean, I started working at home

when our elder daughter was one. So my kids have no memory of me ever working not at home. And I've never had an office anywhere else. I've never paid rent to anybody else. Interesting. Yeah. So. Like I have a talk in Dubai in February, and then later in that week, I have a talk in like Utah

and then Nashville. And so I could just get extra time in Dubai, or I could come home, like I could get home at 5pm and then leave at 9am the next morning. And my agent was like, obviously you're not going to do that. And I was agent was like, obviously you're not gonna do that. And I was like, no, I obviously am gonna do that. Yeah, of course you are. That's how I- Yeah, have you been to Dubai before? Yeah.

Yeah, so there's nothing worth really worth staying for. I sometimes I'll make an exception if I've never been to a place before. Yeah, sure. Or I just did a tour in Europe and I brought my kids, which was exhausting. But we had like, either I'll try to make it an experience or I want to be gone as little amount of time as you want.

100%, that's the way to go. Yeah. That's the way to go. And in 20 years, they'll be gone. Yeah. And you'll be giving this, you'll be giving the sage council to someone else. Well, I thought like, maybe a year and a half ago.

Cause it's the same story over and over, the cast just, it's the same play over and over, the cast just changes. Yeah. Well, I thought about this cause I was like, you know what, I'm like maybe a year and a half ago. Because it's the same story over and over. The cast just changed. It's the same play over and over. The cast just changes. Yeah. Well, I thought about this because I was like, you know what? I'm going to stop working one day. We can just be home.

And then I realized my kids aren't home. I already missed that. Like, I think I generally make pretty good decisions. But it was just like, oh, wait. Like, I might as well be at the office. The other thing I'd recommend doing, young man, is to go on a trip without the kids but with your wife. Yeah, sure.

Cause that those are some of the best things that we have done. The harder to do when you have little kids, but, but later on it was taking a, an event and using it as an excuse to go to wherever, you know, and saying we're, I'm going to X. Do you want to go to X? Sure. We've never been to X let's go. And so build a trip around X? Sure, we've never been to X, let's go. And so build a trip around X.

Yeah, we did that a lot before we had kids. And I would say one regret I have to go to your book is that in retrospect, I took the talks way too seriously, if that makes sense. Like I was, I don't remember whether the talk I gave in Puerto Rico in 2014 was good or bad, but my wife definitely remembers me being very stressed. You know what I mean?

I think that's one of the things I look back on and I go, everything was way too intense. Got it, got it. I don't think anybody remembers whether you're talking Puerto Rico in 2014 was good or bad. Certainly not, probably even the people that paid me don't even remember that I did it. Brian who?

Yeah. Wait, he was here? Certainly no one in the audience. I'm sure if I was dropped into Puerto Rico right now, I could have a vague sense of like which hotel. I think I've been to that Hilton before. You know, I have like, I have just memories of being in different cities and what hotel conference room I was in.

Exactly. I hear you. It's not like so where it's like, oh, have you been to Dubai before? It's like, I mean, I was in. Exactly, I hear you. It's not like, so where it's like, oh, have you been to Dubai before? It's like, I mean, I've been to Dubai, but like I was there for work and I ate in the hotel and then they drove me to a place not in the hotel. And then, you know, it's not. It's worth spending a day, an extra day.

If you haven't spent any time at all in Dubai, it's worth going there, because it's a crazy place. It is. Like go to the top of the Burj. Yep. That's like an hour, an hour and a half. That's worth doing. You've seen the indoor ski mountain, right? I have.

Yeah. So that's worth it, you know, but beyond that, there's not much. Yeah. Last time, last time I was in Dubai in the fall and I had basically, I arrived like at noon and I didn't have to do my thing until the morning. And so I got a haircut. Which is one of my favorite things to do when I travel overseas.

It feels like you feel important getting a haircut in a place that you don't live. You do? It feels weird, it's a weird sensation. To me it's just a, it's an unusual way into a new place. Like I wouldn't go to a, I wouldn't go get my haircut in Milwaukee. To me, it's just an unusual way into a new place. I wouldn't go get my hair cut in Milwaukee. I mean, unless my hair was completely out of control,

but I've got my hair cut in many countries and I make a point of doing that. Why? Because it's interesting. It just gives you, like foreigners don't go to get their hair, don't go to barber shops. And so you get to see things and experience things as you wouldn't otherwise do.

It's why I also have this, I also go against the grain and I'm a big believer in going to McDonald's when you go overseas. Do you just get a sense of what they value or not value? What do they got here? And who's there? What kind of people are there? And like the class differences in certain countries

are vast at McDonald's. What they're offering is amazing. I had actually surprisingly good gazpacho at the, I'm serious, at the Mickey D's in Madrid. So, you know, so those kinds of things that give you a window, give you a kind of a door, sort of side door into a place, I think are interesting. Yeah, it helps you shatter the paradigm too,

because like in America, it's like, oh, everything, you know, you can't raise the minimum wage, the whole system's gonna fall apart. And then you go to some country where minimum wage is like $25, and the thing costs exactly the same. Like the McDonald's price menu adjusted for the currencies is like exactly the same.

Turns out you can still sell a cheeseburger and not fuck over the person making it. And you can get a decent haircut in lots of places. Yeah. Did you ever find that there's miscommunications about the haircuts when you get them in a foreign country? I find that here. That's true. They always ask you like these numbers.

Like I have these numbers memorized. I don't know. Just make it look like it was three weeks ago. And even that is interesting because if you, how do you explain how you want your haircut? And I find that the people are actually, they actually take it seriously because there is that miscommunication and so forth.

And they know it's like, what is this weird dude here who can't even speak the language? And I'd recommend Turkey as a place to get your haircut. I've been to Turkey. Because they use, they like get stuff off of like the back of your neck and whatnot, like with a match.

What? Yeah. They burn it? Yeah, it's cool. That would be, yeah, you would never, I mean, that's not something that you would get. It's cool. So this is my guidance to you, young man,

which is to come back and see your kids, but come back freshly quaffed. Yeah. So what happens is when I don't do that, like it's, you know what? It's going to be too exhausting. I'll stay an extra day and I'll fly. And then you're just sitting around.

You're just like, I might as well get a haircut. Now my last overseas haircut was in November in Dubai. 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.

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You have any other tips for being on the road? I do. Lots of them. It's harder now, but buy a local newspaper. Yes. Look at it, even if you can't read the language. Totally interesting. Another thing that I do in other countries is almost always I go to a grocery store. Yeah. Going to a grocery store. Going to a grocery store in another place is honestly for me is a delight. It's really just those basic daily quotidian things that you don't get being in a Western

international hotel that is kind of generic. Grocery stores, McDonald know, kind of generic. And so grocery stores, McDonald's, Haircut, I always go, not always, but almost always, try to find the highest place in the city. So you can go to, so you can get like a, you know, a vantage point on the whole thing, get a sense of where you are. So there's a-

I love this thing Bill Bryson talks about where he's saying like, what you do when you read a newspaper from a place you're not from is most of the stories which are important to them are funny to you, because they're absurd. You're like, look at this person's name or I can't believe this is what their politicians are doing. Whereas you would be outraged or appalled

at that same thing in your country. Yeah, yeah, yeah, yeah. And then- That's a good point. I hadn't heard of that, yeah. And it kind of turns a good point. I hadn't heard any of that, yeah. And it kind of turns down the volume. You go, oh, most of the news is silly and not that important. And then it also gives you a lens on which,

what other countries think of your country, especially being an American. Cause so often our news is front page news of other countries. Absolutely. And you're like- Absolutely. I think it's funny, like here we're like 50-50 split politically. And in other countries, they're like 90-10.

Like you might every once in a while meet someone who, and you go, oh, okay, this helps me understand where to come down. I don't mean they're 90-10 on their issues. They're probably 50-50 on their issues. But our issues seem so obvious to them. Okay, so on the 90-10, what's the 90 and what's the 10? Well, I'll give you an example.

90 center, I mean, Europe, like 90 center left, 10. Yeah, like people, it's funny, like people think when I talk about stuff politically, they're like, you're gonna piss off half your audience. And I go, well, first off, you think 100% of my audience is American, which they're not. And then you're thinking that the rest of the world is equally split on these issues.

Most of the major Western nations are more or less in agreement on things that America, we really struggle with, like, you know. University healthcare. Healthcare, how do you solve, you know, is there, is climate change real? Exactly, they're just like, these are not partisan issues. Even the pandemic was much less partisan

in other countries. And so that's, you're kind of like- I am though, I have to say, I have this thing, maybe it comes from growing up in the Midwest, where if I'm in another country, I will not criticize this country, if I'm in another country. I will criticize this country.

I will criticize something publicly, you know, in the United States, but if I, I feel like if I'm overseas and an American, I actually kind of represent the United States and I don't want to pee on the shoes of my own country. I feel like, I feel obligated to represent what I think America is, not what they have come to see America through pop culture. Yeah, I hear you.

I can make the argument either way. This is not even an argument for me. This is, it's visceral, it's emotional. No, it's like a value you pick up as a kid. Like some people dress up at the airport because that's what they thought you do. It's interesting when you pick up- I also say please and thank you for everything.

So that's another Midwestern thing. It is funny. Sometimes, though, they'll be like, well, why does America do this? And it's like, well, it's because we're paying for everything else. It's easy to have universal health care when big, large America pays to defend, by and large,

the entire world. And then there's that joke. It's like, you're about to find out why Americans don't have health care when our military has to get involved. You can sometimes see America from different angles from foreign countries, which helps you, oh, this is, we've made this assumption, they've made this assumption, but those are only possible because of these other facts. It's also because someone like you, extraordinarily high income, is paying a relatively modest income tax rate and living in a state without an income tax. Yeah.

So that's part of it too. So you go to Scandinavia and it's 50, 60% income taxes. Yeah. Crazy world we live in. It is, it is. You travel a lot, how do you stay in a rhythm? Cause it can blow up, it can kind of blow up your life. Are you a good routine person on the road?

Barely, I'm not traveling all that much right now. And I'm pretty intentional when I travel. So I do, as I said, I do very quick turnarounds. So for instance, when I work on a book, I don't travel. I shut my calendar. Interesting. Yeah, yeah, yeah. I'm the world's worst multitasker,

the world's worst parallel processor. I'm a complete serial processor. So when I work on something, I want to work on that. I don't want to do anything else. So what I've done for 20 years is, when I have a book, I close my calendar for as long as it takes. And not 100%, but like 90% closed and don't go anywhere. And then when I have something, I'm out all the time.

Are you good at saying no, or do you have to create sort of things so you don't have to even consider a yes or a no? I think that the second way is easier. It just basically, you know, if people say, oh, pink is, pink is off the road for the next six months, people are okay. You know, I think it's easier to have a hard and fast rule. Right. Sure.

It's easier for you to comply with and it's easier for people to take. But is it easier for you to stay true to the rules? Is it easy for you, if you set a rule, are you a person who's tempted to make exceptions to the rules? I mean, I think we're all tempted to do that. The rule is your way to reduce the temptation. I don't think you can dial the temptation to zero. I think the rule gets you to turn that dial down, down, down, down, down, down, down.

Yeah. I'm not good at the, like, I'm going to take things offline. I struggle with that. Yeah. The other thing is, it depends on also how, I mean, I'm still incredibly paranoid. But I was more paranoid 15 years ago when it's like, OK, great. So someone's making an offer.

It's Tuesday. There might never be an offer coming in ever again. Yes. So I better take this. Yes. The insecurity of this is all going to go away. offer coming in ever again. Yes. So I better take this. Yes. The insecurity of this is all going to go away. This can't last forever. Right.

That tends to lead to decisions you'll regret in the future. Absolutely. Yeah. Absolutely. Yeah, because you were thinking it's never going to go away 20 years ago and you're still here. I am still here. Yeah.

20 years later, I'm still here. So things haven't fully gone away yet. Yeah. But that could happen tomorrow, Ryan. Yeah. And you're going to, you're going later, I'm still here. So things haven't fully gone away yet. But that could happen tomorrow, Ryan. Yeah, and you're going to, I think that the thing you worry about is regretting in the future saying no to a thing that you'd be grateful to have then. Yeah, yeah, yeah.

I mean, you can tie yourself up in knots about that. I mean, I really do think that in this kind of stuff, make the best decision you can with the information you have at that moment. And also looking retrospectively, recognize that the person who made that decision is not the person you are today. Yeah. I think speaking is a hard one

because like opportunity costs are hard for people to manage period. But with speaking, it's like, you're sitting there, you're going through your life, you have plans for next month, or you don't have plans for next month. And then someone comes along and says, you wanna do something on, you know, Tuesday the 31st,

and it has a concrete number attached to it. Absolutely, absolutely. And so- This is how, exactly. And you have to say, oh, is that barbecue I'm going to, I'm scheduled to go to, is that worth X? And the answer is no. Yeah, right.

Right, like I just- There are a few things that are the answer is worth yes. It's like, but what I also do, this is interesting. I haven't really thought much about it. I don't really think that I have a system, but what I also do is like for my speakers agent, I do take a lot of dates off the calendar from the get-go. Saying I don't want to, you know, and that way, again,

it's a rule that doesn't require me to make a decision each time. Yes. The rules that absolve you from making decisions every time are great because for someone lazy like me. And then you can't make the wrong decision because you already made the decision. You don't even think about it.

Yeah. Like I was just with my kids, we went down to the beach for a couple weeks. And I got an offer like sort of last minute to do something like towards the end of it. And I was like, one of my goals was to say no more this year. Like I was going to say no more this year. And so I was like, you know what?

No, I'm not going to do it. And then that day comes around. And I'm like, we didn't do anything. We're just hanging out. And so now, like look, what's a wonderful day with my kids worth? A lot. What's an ordinary day with my kids worth? A lot.

But then obviously there's some number in between there that you say yes to, or you would never say yes to anything. But I sort of had to go into that day consciously going, okay, you chose to be here for this day. This doesn't mean you have to make this day special, but it does mean you should actually be here for this day. So I was like, don't disappear into your computer

or your phone in the course of this day, because if you're gonna do that, you might as well be away and be getting paid. Good point. You know, if you're gonna pay to be here. But wouldn't that apply to any day? It does, but because there was a concrete dollar amount to it, it forces you to face the logic of your decision.

You can also do a little bit of kind of mental time travel and thinking and saying, it's hard, but you could say, so you have an eight year old, so go back to, you know, when he, to he? Yeah. Yeah. You know, when did he learn to walk? Like 12, like 13 months somewhere. Yeah, somewhere.

Okay. So how much would you pay to go back in time to see him learn to walk again? Sure. You pay a lot. Yeah. At some point you would pay any amount of money for any amount of extra time with them.

Well, just to go back to that moment. And the thing is that, that is that that moment is happening today. Of course. So this is, I mean, you've seen or read the play, Our Town, right? No. OK, so it's a famous Thornton Wilder play. And so it's about this place called Grover's Corner, New

Hampshire. And I want to use a 50 cent word here. I resisted using the same 50 cent word a moment ago, and I'm going to use it now, which is quotidian. Yes, no, you used it earlier. Oh, I did. Yes, yes. I meant to resist it.

Impressive. All right. So, okay, now it's completely overused, because that word should be uttered maybe once a lifetime, not twice in a conversation. Regardless, it is about the daily, everyday lives of these places and these families. And then there is a tragedy and something quasi-mystical happens and the woman who has

died gets to go back and there's a figure in the play called the stage manager who's kind of like a narrator type. And she says, I want to go back to a very special day. And she says, no, no, no, no, no. You should go back to just an ordinary day. And so she goes back to an ordinary day. She's dead, but she comes back to an ordinary day and she sees her mom and she sees her brother

and it's just heartbreaking. Because you realize all these things are going past us and we're oblivious to them. Yeah, Jerry Seinfeld has a good thing about how parents always want quality time, but he says, give me the garbage time. Yeah. You know, like on the couch eating cereal,

you're watching a movie, you're driving across town. Those are just as good. In fact, there's less pressure. I had a boss actually, who when I had kids, told me that quality time was bullshit. And it ended up being sage advice. Because it just, you just don't know. Yeah.

I try to remind, when I travel with them, we go on trips a lot. I try to use speaking as a chance to go places. I try to remind myself that it's all part of the trip. So like the drive to the airport is part of the trip. You know, like, like I, cause we were in New Orleans, I was doing a talk or something and I had some activity planned for us, some dinner reservation, I thought that'd be excited about it.

We're going to ride the streetcar or something. And there, you know, it's two double beds and they're like jumping from the beds, totally beating the shit out of each other with pillows. And I'm like, guys, stop, we have to go do the thing. And then I was like, this is the thing though. They're loving this and I'm trying to end this to go and they're gonna sit in a restaurant in color.

This is actually more fun for them. And I'm trying to fast forward through what they're enjoying to do the trip, but it's all the trip. The moment we left the house, the trip began. Yep. And it'll be interesting to see from these travels what your kids remember. Yeah.

Because in my experience, it ends up being the things like when somebody forgot their suitcase, or the weird guy who sat next to so-and-so on the plane and started talking to her, or these things that were unplanned and not actually part of the thing, ancillary to the thing,

but ended up being one of the things. Yeah, you got them a private tour to some thing that you only get to do once in a lifetime and that totally forgot, but they remember that the driver had a weird hat on. Yeah, exactly, exactly, exactly. I think that goes to the idea of regrets too, which is like, we think we're going to regret certain things and those are almost never the things

that you actually end up regretting. Well, it depends. It depends. I mean, there's a lot of work on unanticipated regrets. And what it shows is that we sometimes, I mean, this is not my line, it's Dan Gilbert's line. We sometimes buy insurance we don't need. That is we over index on how much

and what kind of regrets we're going to have. And I actually think that it also yields a kind of jarring heuristic about decision-making, which is that most of our decisions in our lives don't matter all that much. They really don't. I mean, truly, they don't matter. And so 10 years from now, I don't

know how much time you spent figuring out what t-shirt to wear today, but 10 years from now, you're not going to care whether you wore the Bruce Springsteen t-shirt or another t-shirt. You're not going to care what you had for lunch today. You might not even care about a trip that you're saying, oh, should I do it, should I not do it? But I think we can make a pretty safe prediction about what

people will care about. Because in this research, I had now 26,000 people tell me what they regretted. And one of the great things, this is another Dan Gilbert line, which is, most people are like most people. Okay, that's a very dirty principle of social science. And so I can make a pretty safe prediction

about the things you'll regret in 10 years, or 20 years, or 30 years, because of the same things that I'll likely regret in 10 years, 20 years or 30 years. And it's not, and most of the decisions we make in a given day are meaningless. It's like finding out what the actual measurable or noticeable like, like I think about this is I'm a pretty disciplined person, I'm pretty routine. And so sometimes I'll find myself getting very stressed. It's like, Hey, I was supposed to start this thing at nine. Not like someone was waiting for me

and I made them wait five minutes, but it was like, I wanted to get in the office and start this project at nine. And because my kid was running slow or there's traffic or whatever, my wife and I were talking, I got there at 9.15. Oh my God, Ryan. Right?

Like there's some part of the- I thought that discipline was destiny. It is, it is. but this is my point, is that as you stress about these little things, you're forgetting that for what you're working on, a book, a career or whatever, 15 minutes is not a measurable quantity. You're not gonna be able to look back in 30 years

and see that 15 minutes made a difference one way or another. It's not like this is the final drive on the final play of a team season, right? And so we end up really stressing about these kind of little choices as if, because cumulatively we think they matter, but perhaps they do matter cumulatively, but it also means individually they don't matter

and you don't have to stress it as much as you think you do. Here's the thing, if you show up more or less at nine o'clock consistently over time, that's a good thing. But the variance within that is irrelevant. Yeah, more or less is a great phrase. I've tried to think about it as more often than not. Am I doing the right habits,

right things more often than not? That's what matters. Give yourself a little bit of grace for not doing that. I look at that with exercise. My view is basically don't go two days in a row without exercising. That's it. And that's a pretty easy thing to stick to.

Yes. So basically more often than not, are you exercising? Exactly. You're getting it right more often than you're getting it wrong, which means you'll get largely the right result instead of largely the wrong result. Right, and do I wanna say, I mean, I guess if I were,

if I were a serious athlete and were really training, I would say, oh, each week I'm gonna run this many miles, but I'm not that. Yeah, this stuff, it's not fentanyl, where like, you know, one dose can be the thing that decides everything. So it's more often than not, are you in the ballpark on time doing the right thing?

That's what cumulatively gets you probably where you wanna go. Absolutely. What are the things that people said they'd regret? Actually, what surprised you about what people said they would regret? Well, I mean, I did a few different things to get at this.

Like I'm a big, I mean, like I'm gonna, can I use another 50 cent word? Epistemological, right? So, it's like, basically, I always, when people say stuff, I always want to know, like, how do you know? Right, and I expect anytime I say something for people to also say, how do you know?

And so, in the research on regret, there were three legs to the stool. One of them was 60 years of research in a whole variety of academic fields. But I also, for this, decided to do two research projects of my own. One was a quantitative survey, a giant public opinion survey on American attitudes about regret,

about which more in a moment. And then I also collected regrets from all over the world. And so we have a database of 26,000 regrets from people in 134 countries. And so what surprised me particularly about that third leg was the universality of it. That really surprised me. I expected much greater variance in what people were regretting.

And there was at the very, very granular level, but there was surprisingly little variation based on nationality, relatively little based on gender, a tiny little bit based on age. And so that's the impression that I got from the qualitative survey. In the quantitative survey, which I did like a pretty serious piece of public opinion work in order to get at demographic differences. And when we crunched the numbers, there weren't that many. I spent all this time and effort and cash to do this, like a really good piece of survey research, over sampling in every category so we can make claims about well-educated people, people with high degrees of formal education like this and women like this. And there were very, very few differences. And so

the universality of the language in the qualitative one, and just the fact that there weren't many demographic differences in the quantitative one surprised me. Because people are people and they're like most people? Most people are like most people. Yeah. And I mean, it's really the case.

What do most, I really think, what do most people want? Most people want, they want some stability in their life. They want a chance to learn and grow. They want, I think most people are good and want to be good. And they want love. And that's true whether you are in Austin, Texas or whether you are in Kuala Lumpur

or whether you are in Dubai. Sure. And so did their regrets reflect choices that took them away from those things? Yeah, yeah, pretty much it. So regrets, see my argument is that regrets operate like a reverse image of what people really want out of life. So the idea is that, let's go back to these decisions that we make every single day.

So if you think about yesterday, you made, I don't know, maybe 50, 60 decisions. You don't remember most of them today. A week from now, you probably won't remember any of them. But there are certain things that you've done or haven't done, decisions or indecisions, actions, inactions, from five years ago, 10 years ago, 20 years ago, that not only do we remember, but they bug us. That's a very strong signal.

Like that's something to pay, that is a signal to pay attention to. And what it's a signal of is what we value. And so we have this big category of things called foundation regrets. Foundation regrets are, I spent too much and saved too little and now I'm broke. I didn't exercise or eat right

and now I'm profoundly out of shape. I never read or studied and now I'm ill-informed and don't have skills. All right, foundation regrets are about, I think ultimately about stability. We have a lot of regrets on boldness. Not being bold enough. Absolutely. Yeah.

Huge. Yeah. And it doesn't matter the domain of your life. I have lots of regrets. If only I'd started a business. You take the number of those people with, I started, my regret is that I started a business and went south on me. Yeah.

You know, 50 to one with, I started, my regret is that I started a business and went south on me. Yeah. You know, 50 to one different, I mean, seriously, I was really surprised by this huge numbers of regrets about not asking people out on dates. You're probably more likely to regret the thing you were afraid to do than the thing you boldly did. That is, I don't wanna say 100% true,

but it rounds to 100%. Yeah. I mean, it really does. And I'll tell you some more about that. I can lock that down. So I have the impression, so huge numbers of regrets about being at a juncture in life where you can play it safe or take a chance. And when people don't take the chance,

most people, most of the time regret it. Not all the time, not everybody, but overwhelmingly. We also see in the one demographic difference I found in the quantitative research and forgive me for getting in the weeds about these two different ways of knowing, but in the quantitative research, the one demographic difference was age. And what you had is that people in theirs had roughly equal numbers of regrets of action and inaction. As people age, 30s, 40s, but certainly 50s, 60s, 70s, inaction regrets took over. You get to your 50s, 60s, 70s, three to one, four to one inaction regrets over action regrets. Maybe the very bold and reckless have died.

Could be. They're a little bit removed from the sample. But I- That's a good argument actually, but you know- It's probably more likely- I don't know if anybody ever died from asking somebody out on a date though. The other reason is that when we do things, we can make sense of it,

we can find the silver lining in it. But when we haven't done something, particularly done something bold, particularly done something meaningful, it gnaws at us for a very long time. I talked about this in my Courage book where I found that the times I didn't do something or I didn't speak up or I wasn't bold enough,

I always had my reasons, but the reasons don't age very well. They clearly won the day in the moment, they were more persuasive, but the efficacy of the argument decays pretty rapidly over time. It's like, oh, like I remember I had this job or this controversial person

and I knew if I spoke up about this thing, I'd lose my job. And so I didn't. But in retrospect with age, I'm like, why would you be afraid? Why would you not wanna lose a job? Why would you be worried about losing a job where speaking up about something that was right

would cost you that job? But you only get that, not only, but that perspective becomes more obvious with time. At 22 or whatever, you don't fully understand it. But the excuses age poorly. That's, I think that's a very, very good point. And I'll see you and raise you a bit. Go into this database, right?

26,000 regrets. And just search for the phrase that you just used or variations of it. Speak up, spoken up, speaking up, massive numbers on that particular phrase. The great thing about people narrating their regrets to you is you get to see their, get to hear, read their actual language. Yeah. And the phrase variations on speaking up and spoken up are massive. It is a big regret that people have and it's a regret of boldness. Now, I'm hoping that some 22-year-old is hearing your tale there and then based on that, tomorrow she's gonna speak up because she

doesn't want to have that regret. Yeah, yeah. You just wish you'd, your chances are you're going to wish you did more. I think that's true across the board. Chances are you're going to wish you did or said more than you're doing right now. I think that's generally true for most of our life.

I mean, you see it in some of these connection regrets where these harrowing stories where people want to say something to somebody really true for most of our life. I mean, you see it in some of these connection regrets where, you know, these harrowing stories where people want to say something to somebody and then they've been and it's too late, they pass away. Whether it's a, we have a lot of regrets about these connection regrets are the regrets that I sort of the language of that is if only I'd reached out and we have a lot of regrets about. Should have made up with my father, should have reached out to my sister, should have apologized. That's, yes, and friendship. Yeah, letting things drift away.

You got it. Yeah. This was it, because when you look at these, when you look at a lot of our relationships, what I've seen, again, just narrated by all these people, is that many relationships fall apart in profoundly undramatic ways. It is not a rift, it is, as you said, it's a drift. And what happens, particularly with friendships,

is one person wants to reach out, and they're going, oh man, it's gonna be really awkward if I reach out to Ryan, because I haven't talked to him for 10 years, and besides, he's not gonna care. So then you wait another five years and it becomes more awkward. And the thing is, that is a major forecasting error on both of them. It's way less awkward than people think.

And the other side almost always cares. And so if you talk about an excuse that doesn't age well, awkwardness. Awkwardness is an excuse that doesn't age well. 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 would really help the show. We appreciate it. And I'll see you next episode. If you like The Daily Stoic and thanks for listening, you can listen early and ad free right now by joining Wondery Plus in the Wondery app or on Apple podcasts. Prime members can listen ad free on Amazon Music. And before you go, would you tell us about yourself

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