How Regret Can Propel You Forward | Daniel Pink (PT. 1)
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I think when things are difficult or we know things are going to lead to hard conversations or changes we have to make in our life, we come up with reasons not to do them. When I think about therapy, I think, how can I make this as easy to do as possible? Whether that's like scheduling a bunch of appointments in a row, whether it's doing it remotely so I don't have to get in my car and drive somewhere.

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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 the most important people in the world,

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. Hey,

I'm 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. It's going to be long and it's going to be for a very short amount of time. I'm going to 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 going to be a short trip because my kids are in school and they can't come. And so I'm not going to be gone very long. I'm actually going to 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. 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 haven't always been perfect at it, but it's what I think about. Like my speaking agent knows like,

The thing is bedtimes, like getting home at 9.30 p.m. 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 going to be in town for a conference. I tried to see if I could fit in

into his schedule, and he did. Dan's awesome. Dan's written like a bazillion New York Times bestsellers, Drive, To Sell is Human, When, A Whole New Mind. And then more recently, he did this book called The Power of Regret, How Looking Backwards Boozes Forwards. And I'm going to split this episode into 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 there was 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 COTA. 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 going to 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's where Stoicism comes from. I did not know that. Yeah. So Stoicism just means porchism. It was a philosophy that was set up in the Athenian Agora period.

- 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 told that story in writing anywhere. - Oh really? - 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. Right. And he passes a bookseller and the bookseller 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 now. Yeah, yeah. Like I associate that with you more than with Socrates. And then sets up a philosophy school in the Agora on the painted porch. And that's where Stoicism comes from. Got it, got it, got it.

That's where the name comes in. And the porch has a big girl on the back. 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? 12 years.

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 it was true. - It's not true. - It influenced my life nevertheless.

Did it influence it positively or negatively? 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. 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. 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 I... 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. So...

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 in how many nights do I have to be gone? Absolutely. I have in my head a rough heuristic of-

how long, 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 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 p.m. But like 11 p.m. might as well be

6 a.m. the next morning. Yeah, of course. Yeah. What really matters is am I home by 7? 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've made in the last 25 years. Is just being around for your kids? 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 5 p.m. and then leave at 9 a.m. the next morning. And my agent was like, obviously you're not going to do that. And I was like, no, I obviously am going to. Yeah, of course you are. That's how I... 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. I just did a tour in Europe and I brought my kids, which was exhausting. But we like either I'll try to make it an experience or I want to be gone as little amount of time as you 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, like maybe a year and a half ago. Cause it's the same story over and over. The cast just take it's same play over and over. The cast just changes. Yeah. Well, I thought about this cause 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. Because those are some of the best things that we have done. Harder to do when you have little kids, but later on it was taking an event and using it as an excuse to go to wherever. Yes. You know, and saying, 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. Yeah.

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? Like, I think that's one of the things I look back on and I go, I, it was way too, everything was way too intense. Got it. Got it. I don't think anybody remembers whether you're talking Puerto Rico in 2014. Certainly not. Probably even the people that paid me don't even remember that I did it. Yeah. Ryan who? Yeah. Wait, he was here? Certainly no one in the audience. Yeah. I'm sure if I was dropped into Puerto Rico right now, I could have a vague sense of like which hotel I'd be like, 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 weird. 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, hour and a half. That's worth doing. You've seen the indoor ski mountain, right? I have. Yeah. So that's worth it.

But beyond that, there's not much. - Yeah, it was just real place. - 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 interesting, 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. Yeah.

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 barbershops. And so you get to see things and experience things that 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. You just get a sense of what they value or not value. What do they got here? You know, 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, kind of a window

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 going to fall apart. And then you go to some country where minimum wage is like $25 and a

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 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...

You know, 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, look at 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 out of like the back of your neck and whatnot, like with a with a match. What? What?

Yeah. Burn it? Yeah. It's cool. That would be, yeah, you would never, I mean, that's not something you would guess. 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 I'm

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. We just had a new employee start with us today here at Daily Stoic and the Painted Porch, an inventory manager. And you know where we found them? We found them on LinkedIn, which is where we hire for pretty much everyone and every position here and have employees.

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Mens sana in corpore sano, a strong mind in a strong body. I think we sometimes think of philosophy as this mental thing, which it is, but it's also a physical thing. The Stoics were active. I try to be active. You should try to be active. You've got to have a physical practice of

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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, 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 in another place is one of my, is honestly for me is a delight. So it's really just those basic daily quotidian things that you don't get being in,

in a Western international hotel that is,

you 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 those are the- 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, 'cause they're absurd. They'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. That's a good point. I hadn't heard 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, because so often our news is front page news in other countries. And you're like, 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, okay, this helps me understand where to come down

I don't mean their 90-10 on their issues. They're probably 50-50 on their issues. Right. 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. So 90 center, I mean, Europe, like 90 center left. Yeah. 10. Yeah. Like people, it's funny. Like people think when I talk about stuff politically, they're like, you're going to 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, universal healthcare, healthcare, how do you solve, you know, is there, is climate change real? Yeah, 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, uh,

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. I can make the argument either way. This is not even an argument for me. This is a...

it's visceral. It's emotional. No, it's like a value you pick it up as a kid. Like people dress up at the airport because that's what they thought you do. That's it. 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 healthcare 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 healthcare when our military has to get involved. You can sometimes see America from different angles from foreign countries, which helps you. Oh, 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, yeah, that's part of it too. So you go to Scandinavia and you know, 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? Like, cause it can blow up. You can kind of blow up your life. You, 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, you know, 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?

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 off the road for these 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 a 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, you know, I was more paranoid before.

15 years ago when you're like, okay, 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. 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. 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, I think 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. I mean, you can tie yourself up in knots about that.

I mean, I really do think that in this kind of stuff, you know, 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 want to do something on Tuesday the 31st, and it has a concrete number attached to it now. Absolutely. And so— Exactly. And you have to say, oh, is that barbecue I'm going to— Yeah. I'm scheduled to go to, is that worth X? Yes. And the answer is no. Right. Right.

Right. Like I just there are a few things that are the answer is worth. Yes. It's like but but what I also do is interesting. I haven't really thought much about I don't really think that I have a system. But what I also do is like for my speaker's agent, I do take a lot of dates off the calendar from the get go. Yeah. 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 of 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 going to do that, you might as well be away and be getting paid. Good point. Yeah. If you're going to pay to be here. But wouldn't that apply to any day? It does. But because there's 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, I mean, it's hard, but you could say, so you have an eight-year-old. So go back to...

you know, when he, it's a he? Yeah. Yeah. You know, when did he learn to walk? 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'd 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,

Like that moment is happening today. Of course. Right. So this is, I mean, if you've seen or read the play Our Town, right? No. Okay. So, you know, it's a famous Thornton Wilder play. And so it's about this place called Grover's Corner, New Hampshire. And.

And you have, 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. 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. 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 he 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.

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. Yeah. Because it's 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 because we were in new orleans i was doing a talk or something and um i had some activity planned for us some dinner reservation i thought they'd be excited about we're gonna ride the streetcar or something and they're uh 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, you know, they're going to sit in a restaurant and 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. We let the moment we left the house, the trip again. 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, uh,

forgot their suitcase or the weird guy who sat next to so-and-so on a, on the plane and started talking to her or these, these things that were like 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. Yeah, exactly. Exactly. Exactly. Exactly.

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We think we're going to regret certain things. Yeah. And those are almost never the things that you actually end up regretting. Well, yeah, but it depends. It depends. I mean, there's a lot of work on on anticipated 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. Yeah. That is, we we over index on on how 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. They, I mean, truly they don't matter. And so, you know, 10 years from now, I don't know how much time you spent like 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, there's another Dan Gilbert line, which is most people are like most people.

Okay. That's a very sturdy 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 in 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 as 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 you- I thought the 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. It's not, you're not going to 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 ended up really stressing about these kinds of little choices as if, because cumulatively we think they matter, but yeah,

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. That's 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, do I want to say, I mean, I guess if I were, if I were a serious athlete and we're really training, I would say, oh, each week I'm going to run this many miles, but I'm not that.

Yeah, this stuff is 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 want to 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 going to, can I use another 50 cent word? Epistemological, right? So it's like, basically, I always, when

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? Yeah. 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. Like I spent all this time and effort and cash to do this, like a really good piece of survey research, oversampling 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. I really think, what do most people want? Most people 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. Yeah. 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, pretty much it. So regrets, see, my argument is that regrets operate like a reverse image of what people really want out of life. Yeah. Okay. 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 know, you made, I don't know, maybe 50, 60 decisions. You don't remember most of them today. Yeah. 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. Yeah. 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

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, 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 different. I mean, seriously, a huge, I was really surprised by this huge numbers of regrets about not asking people out on dates. Yeah.

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 want to say 100% true, but...

it rounds to 100%. Yeah. I mean, it really does. And I'll tell you, I'll tell you some more about that. I can, I can lock that down. So I have the impression. So huge numbers of regrets about, about being, being at a juncture in life where you can play it safe or take a chance. And when people, 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 their 20s had roughly equal numbers of regrets of action and inaction. And as people aged, 30s, 40s, but certainly 50s, 60s, 70s,

Inaction regrets took over. Yeah. You get to your 50s, 60s, 70s, it's three to one, four to one. Inaction regrets over action regrets. Maybe the very bold and reckless have died.

And so they're a little bit removed from the sample. But that's a good argument, actually. But, you know, 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 have 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 want to 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. Yes. At 22 or whatever, you don't fully understand it. But the excuses age poorly. Right.

I think that's a very, very good point. And I'll see you and raise you a bit. Go into this database, all right? 26,000 regrets. And just search for the phrase that you just used or variations of it. Speak up. Yeah. Spoken up. Speaking up. Mm-hmm.

massive numbers on that particular phrase. The great thing about people narrating their regrets to you is you get to see their, you get to hear, read their actual language. 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, 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 going to speak up because she doesn't want to

Yeah, hopefully. Have that regret. Yeah, yeah. 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, 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. Yeah. Whether it's a, we have a lot of regrets about

These connection regrets are 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. Yeah. 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...

And 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. It's going to be really awkward if I reach out to Ryan because I haven't talked to him for 10 years. And besides, he's not going to 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. Yes. And so if you talk about an excuse that doesn't age well, awkwardness. Awkwardness is an excuse that doesn't age well.

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