Dan Pink | The Power of Regret

Srini Rao

Dan, welcome to the Unmistakable Creative. Thanks so much for taking the time to join us.

Dan Pink

Thank you for having me. It's great to be here.

Srini Rao

It is my pleasure to have you here. You have probably long been requested as a guest by many of our listeners. I wanted to interview you for a long time. As I was saying, I read all of your books. You have a new book out, The Power of Regret, which we will get to in great detail. But, given your background and what I know about you, I wanted to start by asking you what social group were you a part of in high school and what impact did that end up having on where you've ended up with your life and what you ended up doing with your career?

Dan Pink

Wow, it was such an interesting question because I actually never thought about that before. And there might be a retrospective revelation here. So there was two parts. The first one is what social group was I part of in high school? I was basically not part of any. I was pretty much, I mean, I was friendly with people, but I spent a not insignificant time alone.

Srini Rao

Yeah.

Dan Pink

And if there was any group that I was part of, it was the school newspaper. I think that was a transformative experience for me. So, so what does that say about me today? It means that, wow, lo and behold, this kid who was sort of a loner ended up working for himself and becoming a writer. What big surprise. The child as a, I think it was Wordsworth said, um, the child is the father to the man.

Srini Rao

Well, you mean, but the nature of your work is so contingent on your ability to connect with people based on what I've read from all of your books. I mean, there's it seems to be like this deep amount of research and conversations with people that goes into it. I watched your TED Talks. I mean, you just seem to have this sort of natural charismatic ability to connect with an audience. So how do you connect the dots between being a loner in high school and developing those kinds of social skills?

Dan Pink

Well, I think that I developed those kinds of social skills after that. I don't think I, you know, I don't think that's unusual for adolescents not to have great social skills. I think that I developed them later in life, but I am, you know, much more of an introvert than an extrovert. But, you know, I actually am perfectly comfortable with solitude. I'm perfectly comfortable being alone. I have a...

Srini Rao

Yeah.

Dan Pink

very, very small group of close friends. I prefer spending time with my wife and our kids more than anybody else by orders of magnitude. And so that's just, you know, that's just, I think that is how I'm wired. And I think that, now that said, I do think that I've developed a little bit of what you might think of as bilingualism, and that I can actually cross the border and speak another language. And...

talk to people and I enjoy doing that, but I think my natural state is alone and quiet.

Srini Rao

Well, I think that if I remember any quote that has ever stood out to me from any of your talks, it's, I think your talk on Drive where you say that in a moment of youthful indiscretion, I decided to go to law school. And I wonder what kind of, yeah, well, that stuck out to me so much because I kind of feel the same way about business school. I always wanted to steal that quote and be like, well, I guess Dan kind of already did that. So, but I wonder.

Dan Pink

Forgive me for laughing at my own joke, but it's pretty funny.

Dan Pink

Ciao!

Srini Rao

What kind of guidance did your parents give you in terms of career paths? Because when you grow up in an Indian family, there's sort of this clear, you can be any kind of doctor, lawyer, engineer, you wanna be narrative.

Dan Pink

Yeah, it's similar to that. I mean, I think that there's a, you know, I think that there, whether it's a South Asian family or an East Asian family or in my case, a Jewish family or any kind of family that isn't patrician and came over on the Mayflower, there is a sense of striving. And I think that's that striving is embodied in a kind of risk aversion.

And the risk aversion suggests that there are, you have to do something that is going to give you some degree of security. And what that meant, especially if you were reasonably good at school, as many people, again, not to stare at you, but many people in the kinds of cohorts we're talking about tend to be, then, you know, if you were good at math and science, you could, you know, become a lawyer, a doctor.

or maybe an engineer. I think Dr. Woods had a higher status in engineers in many of these groups. Don't you think? And then, yeah, and then if you were a kid like me who was fairly facile with words, you could become a lawyer. And those are the professions that gave you some degree of economic security. It gave your family, I think, a sense that you were gonna be okay. And...

Srini Rao

Yeah, it does. It still does.

Dan Pink

And that's exactly why I went to law school. I mean, I was an idiot in a way, I mean, when you think about this, because I'm sort of embarrassed even to say this, but I went to law school. I actually never considered not going to law school. I always just assumed that that's what I was going to do, because that's what you did for exactly the reasons you're saying. And. And just, I mean, I'm truly embarrassed to be saying this, but like I went to law school having never visited a law school. I went to law school.

having never sat in on a law school class. I went to law school having never talked to anybody about what it was like to be a lawyer.

Srini Rao

Well, I did the same. I went to Berkeley having never visited the campus. And I always think to myself, man, if I had visited what I have gone to UCLA instead, I remember my high school band director telling me, he said, you're gonna give up girls sunbathing on lawns to go to Berkeley. And I thought to myself, you know, the weather sucks here. This city is kind of a dump the first time I saw it. And it's funny because I don't remember, you know, having the greatest time. I have fond memories of the place, but I don't remember being particularly happy while I was there.

Dan Pink

Hmm. Mm-hmm.

Srini Rao

Which raises this question, you know, to go back to your earlier book, A Drive, about this idea of autonomy, purpose, and mastery. And I feel like those things are so left out of our education system. You know, like those kinds of concepts were things that I was never exposed to in college. It was more like, hey, here are the paths, here are the majors, choose from the options in front of you, ignore the possibilities that surround you. And given your research,

Dan Pink

Yeah.

Yeah.

Srini Rao

that you did around all of this. I mean, I think it also ties perfectly to regret. What do you think that we should change about undergraduate education to help people find autonomy, purpose and mastery? Because I can tell you, no decision I ever made about my career until I started doing this was driven by those three factors.

Dan Pink

Oh my gosh.

Dan Pink

Yeah.

Dan Pink

Yeah, I mean, I think that. To some extent, if you're only focused on undergraduate education, it's a little too late. I think the problem begins far earlier in elementary and certainly secondary education, and I don't think there's, I don't think that there's a simple, I don't think there's a simple solution for this at all. I think that there might be a set of design principles that could be useful. Um, in, um, in, yeah, among the things is, is to give.

Srini Rao

Yeah.

Dan Pink

is to, there isn't a huge amount of autonomy in, especially in elementary and secondary education. And in fact, actually, what it often rewards, what those systems often reward is not intellectual engagement or creativity or even excellence. Sorry about that. What it rewards, what these systems tend to reward is compliance. What these systems tend to reward is...

Srini Rao

noise.

Srini Rao

Mm-hmm.

Dan Pink

respect for authority and giving the authority figure what he or she wants neatly and on time. And I think what it does is that it inculcates this, what you have in elementary and secondary education is you sort of have the good kids and the bad kids in a way. The good kids are compliant, the bad kids are defiant, but nobody's engaged. And the reason for that is that it's a system built, it's a system built on control.

and control leads inevitably only to those two kinds of behaviors, compliant behavior or defiant behavior. So, you know, even things like in elementary, even elementary classrooms where the teachers focus on, and this is not a knock on teachers at all, but, but it just sort of in their professional training, they focus on quote unquote classroom management that a lot of what teachers do is just try to keep control of the classroom in some way. And so,

So what happens is that you go through 12 years of that and you get to undergraduate and hey, it's not a surprise that people aren't autonomous. It's not a surprise that people aren't pursuing mastery. It's not a surprise that people don't know why they're doing things. So forgive that long-winded answer, but I think that undergraduate really doesn't quite, really doesn't quite get to it. Now, beyond that, I think there are a few other things. So allow me to rant for another few minutes.

Srini Rao

No.

Srini Rao

Please yeah.

Dan Pink

One of the things, so both, if we think about both say secondary education and undergraduate education, I think that we are still way, way too segmented by disciplines, way too segmented by disciplines. And this is also a function of how universities are where there's basically, there's very little incentive.

for scholars to work across disciplines, especially before they get tenure. What you're incentivized to do is become a narrow and narrow specialist. And so as a consequence, the undergraduate education that's offered is very rarely cross-disciplinary. And yet when these young men and women go out into the world, all of the problems and issues they confront are inherently multidisciplinary. I've never gone out into the world and anything that I've done

done in my 50 plus years on this planet, or let's say my 25 years in the workplace, I've never had a problem come to me and say, hello, Dan, I'm an English problem. I'm a math problem. I'm a social studies problem. It comes to me, it's like, this is a big honking problem. It's not clearly stated. It doesn't have a single right answer. And you're going to have to sort that out. And I think that there's a... So multidisciplinary would help, self-directed would help. I have always been a big believer in the importance of arts education in a very hard-headed way. I actually think that, you know, I'm on my lone crusade that both data science and studio art or musical, you know, that high school should teach both data science and statistics and require

Dan Pink

some form of arts and not only not art history or art appreciation but actual either the performing arts or the visual arts or something that involves expression. And so anyway and then one more rant here is that I've actually been very disappointed in seeing the quality of instruction at elite institutions, elite colleges and universities. It's just a lot of the instruction is just not very good and I like I don't know how it's tolerable.

Srini Rao

Yeah, well, you're preaching to the choir. I mean, yeah, as a Berkeley undergrad, I.

You completely agree. Like people brag about the number of noble laureates. And my dad is like, yeah, just because somebody has a noble laureate, cause my dad's a professor. He's like, doesn't mean they can teach. In fact, many of the noble laureates are the worst teachers. Um, but it's interesting you bring up arts education because I, I spent, you know, a formative period of my adolescence in Texas. And one thing that always stood out to me was the fact that music education was mandatory in Texas. Granted, there's nothing else to do in Texas because, you know, all you have a football team. So naturally band is, you know, a byproduct, but I will tell you to this day,

Dan Pink

Oh.

Dan Pink

Mm. Yeah.

Srini Rao

was hands down one of the greatest gifts I ever got from my time in Texas was a incredible music teacher who actually taught me how to practice, how to get better at things that I had no natural aptitude for.

Dan Pink

Exactly. Well, I mean, and that's the thing about, I mean, that's the thing about the arts. And that's the thing, it's like we have, so we have clues about how to reconfigure education from exactly your experience there. So one of the things that irritates me, and as you can tell from talking to me, that list is extraordinarily long. One of the things that...

Srini Rao

Well, yeah, trust me. I asked the question for a reason. I knew that you know, you're the person who I could have this conversation with

Dan Pink

Yeah, yeah, yeah. You certainly poked it here. The, it sort of irritates me when people say, especially about adolescents in high schools, oh, they're not motivated, they're not motivated. Because then you write a book about motivation, people ask you about motivation. It's like, oh, what can we do to get these high school students motivated? They're not motivated, they're not motivated. And my view is like, oh, well, they think that you're.

incredibly boring and controlling classrooms sucks and I don't blame them. But let me show you where they're motivated. Have you seen them in the in theater? Have you seen them on the athletic field? Have you seen them in the marching band? Have you seen them in the orchestra? Have you seen them in the school newspaper? Those people are super engaged. Why? What is it about those elements that make them engaged? Well, number one, it is freely chosen.

So no one is forcing you to be in the marching band. No one is forcing you to be on the school newspaper. It's your choice. Second, it involves other people. And think about marching band. One of the best lessons that one can learn from marching band, I think there are two huge lessons that you learn from marching band. One, practice matters. When you practice, you get better at something. Two, your performance affects other people's performance and their performance affects you. So you gotta bring your A game.

And so those things are collaborative. And the second, I think the third is, I think actually really important is that it's real. It's real, it's out there, it's public, it's in the world. It's not this hermetically sealed terrarium kind of exercise that you have where you write an essay for your English teacher and he or she quickly reads it once and then it disappears. You write a story for your school newspaper and in your small community, people will read it and maybe talk about it and point out where you're wrong.

Srini Rao

Wait.

Srini Rao

Yeah.

Dan Pink

When you are playing in an orchestra, people will listen and watch and say, wow, you really hit the right notes. I really liked that interpretation of the piece of music or wow, you were really phoning it in. You play on an athletic field and it's public. And so we have clues. We have clues about how to configure education. We wanna give people a choice. We want them to learn these habits of the heart like practicing and collaboration. And we wanna do something that is real.

that actually has an impact on the world.

Srini Rao

Mm-hmm. Yeah.

Well, you know, I can't help but think a bit about intrinsic motivation because I'll tell you one thing, you know, Indian parents always have this experience. And I think every Indian kid has had this experience. Russell Peters, the comedian, has a joke about it. It's like you hear about some kid at school who gets five dollars for every day. You come home and have that conversation with your Indian parents. They're like, you're an idiot. You get a meal on the table and a roof over your head. And I that was very distinctly the conversation my dad had with me. I mean, not in those exact words, but I realized the benefit of that.

Dan Pink

Yeah.

Yeah. Ha ha!

Srini Rao

he was teaching us the power of intrinsic motivation. Granted, you know, we weren't motivated to get your grades intrinsically, but it played out later in life. Um, so one thing, knowing what you do, you mentioned that you're a parent. Uh, how do you think about raising your kids having all this information? Because I remember talking to Daniel Coyle about this saying, you know, I wish my parents had been like practice for 10,000 hours. And he said, yeah, usually those are the kids that parents fuck up. Um, and so I wonder how you balance knowing everything,

Dan Pink

Yeah.

Srini Rao

performance and you know like especially all this research you've done under a grant with also giving your kids the freedom to make the mistakes they're gonna inevitably make.

Dan Pink

Yeah, I mean, I don't know whether I do it perfectly, and I'm not sure how much, you know, whatever knowledge I have brings to bear on that task. My kids right now, I mean, my kids have already graduated from college and I have another kid who is in college. So they are well on their way. And I think that what my wife and I tried to do was really be humble about, as much as we could, about...

what we know, what we knew and what we could influence and what we didn't. So I think that beginning it from a place of humility is really important. I think that what's really important is to square, is to combine both sort of high expectations and support. And what that means is so to have your parents

offer only support. And so anything the kid does is great. Anything that the kid does is wonderful and the kid doesn't learn how to pursue excellence or try new stuff. Then you have only high standards without support and the kids become this ball of anxiety. And I think what you wanna do is you wanna have high expectations and you wanna have support and you wanna confer as much autonomy as you possibly can on the kids. And I think that sometimes kids don't always realize that. And you know.

So, like, I truly, like, with my kids, whatever they're pursuing, I truly don't care what they pursue, what profession they pursue, what interests they pursue. I honestly do not care. I'm not sure my kids actually believe me about that, but I truly don't, but I mean it, I truly don't care. If one of my daughters said, you know what, I want to start, I want to, I want to open a store of,

Srini Rao

Hahaha.

Dan Pink

of sports memorabilia. I would say, cool, if that's what you wanna do, do it. What I do care about is that they are honest, trustworthy people, which they are. I do care that they work very hard and that they care, and I do care that they make a contribution. But the realm in which they do that, I don't give a shit about, honestly. But I just think, I'm not sure kids necessarily, and I think that I'm not an outlier on that among parents. I just think that kids sometimes don't believe that.

Srini Rao

Mm-hmm. Yeah.

Dan Pink

It's hard to understand parental love before you're a parent.

Srini Rao

Well, it's funny because I'm not a parent and I ask all these questions about parenting because we have a lot of parents who listen and I, you know, I have this misguided idea that I'm going to have all this knowledge. But my friend Sarah Peck basically put it well. She said parenting is just a giant shit show. She was like, basically, you tell the kid we're going to screw you up and your job is to fix everything that we screwed up in therapy.

Dan Pink

Yeah, yeah, or your job. I mean, you know, you have to have, there needs to be a parental Hippocratic Oath, which is like your first job is to do no harm.

Srini Rao

Yeah. Easier said than done, probably. So one more question about this, which I think will make a perfect segue into talking about the book.

Dan Pink

Yeah.

Srini Rao

One thing I realized looking back as the person who got fired from all my jobs after looking at it through your research was that we don't really hire for autonomy and purpose and mastery in most organizations. We hire for compliance. We reward compliance like it just continues when you get into the adult world. I mean, I think it's changing a lot because I think that I graduated business school April 2009, probably, which is why I was familiar with your work, which was a terrible time to get out of school. And it made me just question.

the entire system. But at some point, I finally came to this realization that wait a minute, it's not that I was a terrible employee, it's that there was this constant mismatch between talent and environment and skill and environment, where there was no way when you don't align talent with strengths and put somebody in a job that you could give them autonomy, purpose and mastery. Why do we do that? Because I can tell you this, as somebody who's been on performance improving plans, like these don't improve performance, they prevent all they do is prevent.

Dan Pink

Hmm. Mm-hmm.

Dan Pink

Uh huh.

Srini Rao

wrongful termination suits. I know that for a fact because then they can say, oh, we made an effort.

Dan Pink

Of course. No, that's their only purpose. That's their only purpose. They are exactly, that's it. Performance improvement plans are a joke. They're basic, they're insurance against employment discrimination litigation. And they are, for certain people, they are not so subtle signals that it might be time to look for a new job.

Srini Rao

Oh, it was not a subtle signal at all for me. Like the minute I heard those words, I was like, all right, I got three weeks to find a new gig.

Dan Pink

Yeah.

Dan Pink

Yeah.

Srini Rao

So how do you change that in an organization? Because like, you know, I think, like I said, it makes a perfect segue to regret because I regret taking a lot of the jobs that I did because I didn't think about them through this lens. Like now, if I went into a job interview and I got a bad feeling, I remember very distinctly interviewing with this guy at some, this was like the very last job interview I had for a real job before I got my book deal. And I walked in.

And the guy was like, when we say, and I wrote about it in my book, he said, when we say eight o'clock, we mean eight o'clock, not eight fifteen. And I remember thinking to myself, if I had the balls I do now, I would have looked at everybody in that room and say, you know what? I think I would fucking hate working with all of you. Thank you for your time and good luck with your hire. And they fired the person they hired for that role and everybody else on that team. About three months later.

Dan Pink

Yeah, yeah, yeah. Yeah, I mean, I wish that would be very cinematic to do that. Yeah, so I guess the question is why? And I think that the, it's interesting, I'm not sure.

Srini Rao

Yeah, of course I would.

Srini Rao

Yeah.

Dan Pink

I think it's a super, I think it's a super, I think it's a really, really interesting, I think it's a really, really interesting question. And I'm not sure, but I think part of it is this, that.

In previous organizations, for a long time in the economy, you actually wanted people to be compliant because people were doing routine tasks. They were doing the same task over and over again, either with their bodies or with their brains. Compliance actually led to efficiency. But now a lot of those routine algorithmic tasks are actually being done by software, by machines.

And so what people are doing more and more is tasks that require more judgment, creativity, discernment, and as a consequence, and, but, but our organizations aren't, our organizations don't have the legacy of that old way of doing things. And they haven't, they haven't shaken that up. I think that's one thing. The second thing is that I think that, that managers for a long time have been thinking that their job is to control people, their job is to, their job is to control people. And

That is, that's a huge mistake.

The other thing about it is that I'll give you another thing. The other thing about control, third reason is that, and I think this is a big factor. I don't know whether you've seen this in your career and your work, but it's also easier. All right, so let's go back to the first principles of drive here for a moment, which is that we have 50 years of research telling us this, that if then rewards, certain kind of reward, if you do this, then you get that. If then rewards are actually pretty effective for simple work with short time horizons. They work pretty well.

Srini Rao

Yeah, please.

Dan Pink

We love rewards, so you dangle a reward in front of somebody, you're gonna get them to focus narrowly, and that's good if they know exactly what they need to do and exactly how to get there, okay? So that's, all right? But the problem is that we have less and less of that kind of work going on in workplaces, and we also have the same body of research tells us that if then rewards are less effective, significantly less effective, for complex tasks with long time horizons. And yet,

We still haven't remade our compensation systems, our incentive systems, our overall structures because we're basically need a, not sure the right metaphor here, we need like a software update or something like that. We're running Windows 95 and that's why the system keeps crashing.

Srini Rao

Well, I think that makes a perfect segue into talking about the power of regret. One question I have for you is...

What was it that led to you writing this book? Like why was this the sort of natural follow-up to Sell As Human? And then one of the other things I've always admired about your books is that they're easy to read. And I know that a lot of work goes into them. Like I find your books are a breeze. Like I can get through one of your books in less than a day because they're just enjoyable. They're easily digestible. You take these very complex ideas and you make them accessible to the average person. So talk to me a little bit about

Dan Pink

Thanks.

Dan Pink

Well, first, I really appreciate you're saying that. Honestly, I really, really do, because I work extraordinarily hard to do that. And that to me is one of the highest values I have as a writer and one of my biggest frustrations as a reader. So I really appreciate that. And it's a product of a lot of, okay, so let's go to, so we'll come back and talk about why I decided, why my midlife crisis led to a book about regret in a moment, but for now.

Srini Rao

and then you know.

Srini Rao

Hmm. Yeah, so what is the process for that?

Dan Pink

The process is, well, it takes me a very long time to write books. And essentially what I do is that I will begin with a very, very rough idea of what the topic is and what kinds of things I might want to explore. And then I start doing some research. And then at a certain point, I hit a certain point into the research.

I begin to see in my mind's eye a structure of the book. And for me, again, your mileage, I don't know whether in your book it was the same, but other writers' mileage may vary, but for me, structure is everything. Structure is everything. If I can figure out the structure of the book, my life becomes an order of magnitude easier. And so I start thinking about the structure of the book based on a little bit of research, and I come up with an initial structure.

It very rarely holds, but it gives me a place to start. And so once I have that structure, I go back and do more research. And then I start stress testing the structure and realize where it's weak and where it's strong. And then at a certain point, again, it's all pretty intuitive, I will start writing some portion of the book. And it really depends. Sometimes at the beginning, sometimes somewhere in the middle.

Srini Rao

Yeah.

Dan Pink

And when I do that, I begin to have new insights into the structure and new insights into the holes where there's more research. And at a certain point, I realize that in the research where I keep hearing the same things over and over again, I'm done indulging myself on the research. And what I really need to do is start writing. And when I start writing, once again, I see weaknesses in the structure, but the structure begins to become clearer and the meta structure often becomes obvious to me.

And then it's all about executing things, sentence by sentence, paragraph by paragraph, page by page, chapter by chapter. Now, the other thing, so, keep saying, like, on another thing, I sound like DJ Khaled, another thing that I do is I write multiple drafts of every chapter, and, and this shows you my obsession, is that I...

read out loud every sentence in the book at some point, often multiple times, and my wife will read every sentence in the book out loud to me at some point. And then I'm merciless about—the way I look at it, every word in that text has to fight for its life. It has to look at me and tell me why it doesn't deserve to die.

Srini Rao

Yeah.

Dan Pink

essentially almost every nonfiction book I've read in the last 25 years was a little too long. And about a third of them, a third of them would have been twice as good if they were half as long. And so I try to be as concise as possible. So anyway, so forgive that again, another long-winded answer here. But it's about structure and about...

Srini Rao

Yeah. Ha ha ha.

Srini Rao

No, no, this is fun. No, I love it. Well, like I said, I mean, I, yeah.

Dan Pink

It's about structure at the macro level, and at the micro level, it's about making sure that every element fits together. One of the things that bugs me as a reader is the amount of filler in some of these books, where it's like, you know what? Let me give you an example from the Regret book, and then I'll shut up for a moment. In the Regret book, I did probably a month's worth of research looking at...

Srini Rao

Yeah

Dan Pink

how regret develops in kids. At what point, because regret is such a sophisticated way of thinking, it's such a sophisticated kind of combination of motion and cognition that little kids can't do it. Little kids don't understand it. Your brain has to develop past a certain point where you have the muscularity and dexterity and experience to process regret. And so there's a lot of research in developmental psychology on this, and I spent about a month looking at it. And to my dismay,

When I started writing about it, I was like, shit, there's really just one thing to say here. And this month of research that I did, it's probably two paragraphs, and that's it. And that's a bummer. But what would be more of a bummer is if I tortured readers and say, you know what? Because I spent a month working on this, you're gonna pay. And so I'm gonna, I'm going to.

Srini Rao

Hahaha!

Dan Pink

I'm going to give you nine pages of this because I found it out.

Srini Rao

Yeah.

Well, it's funny because I can't help but think of Stephen Pressfield's books. Like I will tell you, my most successful book was a self-published book that became a Wall Street Journal bestseller. And I remember the whole thing was like 85 pages. I don't think there was anything in it. There were chapters that were literally probably five sentences. You know, I basically took sort of the Stephen Pressfield approach. And I remember when Penguin acquired it, my editor sent me a note saying, I wanted to talk to you about the structure. I was like, what? She's like, there isn't one. Like, I'm aware of that.

It wasn't my intention. My intention was to make it easy to read. And of course, to your point, I had to learn how to structure things. But what unlocked that for me was something Jennifer Loudon told me. She said, your structure has to be linear, your process doesn't. When I got that, that changed everything. Yeah.

Dan Pink

Hmm.

Dan Pink

Exactly, that's a great way to put it. That's a great way to put it. I hadn't heard that before, but that's exactly right. And essentially what you're doing here is that you're figuring out the structure, you're pushing relentlessly toward clarity to make it easy on your reader. That's exactly, that's a really important point. And I find that with a lot of books.

People simply haven't worked hard enough. They haven't pushed the material hard enough to make it clear. They haven't actually found their structure. They found a little maybe or perhaps a wobbly structure. And they're including things that are extraneous. I'm not saying that every book has to be short. I don't mean that at all. What I mean is that, is that as a writer, you are asking, the thing that you're asking from readers is extraordinary. You're saying, hey, reader, please plunk 20 bucks of your hard earned money on this thing that I made.

Oh, and by the way, I'm going to need you to spend seven, eight, nine hours with it, going through it, reading it. And those seven or those seven, eight, nine hours you're reading this are the opportunity costs of that are you're not going to spend time with your family, you're not going to exercise, you're not going to answer your email, you're not going to call on customers. That spending time with me is the highest and best use of your time. And it's like, it's like, okay, I'm sorry.

I gotta make that worthwhile. I'm sorry, I gotta make that useful to you. I'm sorry, I gotta make sure that you end that experience saying, holy crap, I'm so glad I spent eight hours or nine hours with Dan rather than going to the gym or answering my email or hanging out with my kids because I got so much out of it. And so I think that the bar is extraordinarily high, which is why I'm so delighted when I read a book that actually meets that.

Srini Rao

Well.

Srini Rao

Well, speaking of a book that has met that bar and one that I don't spend my time, I didn't regret spending my time doing exactly what you said. Let's talk about yours. Now that I've talked your ear off about everything other than the book, what led to this book?

Dan Pink

No, I'm happy. No, listen, I'm happy. I'll talk about, you know, again, it's your show. I'll talk about anything you want. I mean, I'll talk about the dating show that you were on, too, if you want to talk about that.

Srini Rao

Well yeah, I wanna go into the book too. I have a lot of questions about the book.

Srini Rao

We'll come back to that since there might be a nice tie in to regret although I don't regret that and we can talk about that when we get to certain sections Yeah, well, yeah, but let's get into those like, you know, why a book about regret like what was the read? What sparked this as your next book?

Dan Pink

No, I don't think you should. I thought it was awesome, actually.

Dan Pink

Well, part of it was, you know, I'm about 10 years older than you, and so you might have not have had this jarring experience yet, but you will, young man, trust me, is that you will at some point realize that through no fault of your own, you have mileage on you, and that when you look back, there's room there. When you go to an online forum to put in your birth date, your birth year,

Suddenly you're scrolling much more than you ever did. And that's kind of alarming to look back and say, wow, I got some mileage on me. But at the same time, at my age, in my 50s, I feel, I mean, I hope that I have some mileage ahead of me. And I wanna be able to, and I wanna, so you have this passage of time and you wanna say, I wanna use that time well. I don't wanna throw away my shot.

Srini Rao

I already feel like that.

Dan Pink

And so what can I learn from what's happened that I can apply going forward? And so that was a big part of it. And also one of my daughters graduated from college and that was sort of, I was thinking, how do I have a kid who's graduated from college? I'm 26. And what I realized is that I had regrets. And what was interesting is that having regrets, when I talk about them with people, instead of recoiling.

which is sort of what I expected people to do, they leaned in, they wanted to talk about this. And then I went and looked at the research and I was like, crap, I think we've gotten this wrong. And so it was a topic that was like really meaningful to me because I was trying to sort it out myself. You know, it's just the old line in, especially in social science, that all research is me search. And so I think that was somewhat true here.

Srini Rao

Mm-hmm. Yeah. Well, I think I had to agree with that. Well...

So one of the things you open the book by saying is that regret is not dangerous or abnormal, a deviation from a steady path to happiness. It's healthy and universal, an integral part of being human. Regret is also valuable. It clarifies its instructs done right. It needn't drag us down. It can lift us up. And I remember very distinctly, I don't remember the exact line, but I underlined it. It was about this whole idea of no regrets living. And you said it turns out that that's utter nonsense. Where do, so, so why is it that, you know, this sort of, you know, popular platitude

Dan Pink

Yeah.

Srini Rao

regrets but the reality is what you're talking about.

Dan Pink

I think that we're well, I think it's a bunch of different factors. And it was all of these things. There's a mix of, there's a mix of, there's a mix of good and bad. Um, we are over indexed on positive. We, especially Americans, we are over indexed on positive emotions. And we've been taught somehow that you should always be positive. You should always think positive that you should banish that you should banish the negative, that you should always look forward and never look backward. And here's the thing.

Srini Rao

Hahaha!

Dan Pink

That's a really bad idea, but it comes from a decent place because what we know is that positive emotions are enormously important. You wanna have positive emotions. There are benefits to optimism. You wanna have more positive emotions than negative emotions. But the thing is we've gone too far in saying that you should only have positive emotions and that negative emotions, particularly our most common negative emotion, regret, is somehow dangerous, that it weakens you. So I think that's one part of it. The second part is that

We, again, I think meaning Americans, but I think people more broadly, haven't been, no one ever teaches us how to deal with negative emotions because of that. And that's a huge problem because negative emotions are essential to healthy living if we know what to do with them. And so what happens is that when we feel negative emotions, we, one tendency is to ignore them.

Because you're like, oh no, this is not real, this is not legit. I don't feel positive, la la, put your fingers in our ears and start humming. And that's a really bad idea, particularly when it comes to regret. But on the other hand, sometimes we get taken over by these negative emotions and we wallow in them and we ruminate on them and that's an even worse idea. And I think it's because we've left people adrift. We haven't given them the tools, the mechanisms, the processes, the simple steps to deal with negative emotions.

What do you do when a negative emotion knocks on your door? And most of us have no freaking idea and that's a huge problem. And I also think going back to our earlier part of our conversation, I think it's a reason that you have so many people in secondary school and in university who are unhappy and who are wrestling with some mental health issues. They're experiencing negative emotions, they think they're the only ones and they're hobbled by.

And no one's given them instruction on how to deal with it.

Srini Rao

Yeah, it's funny because I've gone out of my way to find people just like you for the show because I kind of wonder how much of you think is the self-help industry is to blame for all of this because I think there's this almost sense of delusional optimism. The other thing I think that the self-help industry is notorious for is ignoring context where it's like, hey, here's this blanket formula.

Dan Pink

Hmm.

Srini Rao

you know, for success. I'm like, wait a minute. There's one massive fucking variable that throws off every one of these theories and that's the person.

Dan Pink

Yeah. And, and, you know, again, you know, a lot of the stuff in the self help literature isn't rooted in anything. It's rooted in what that person is thinking. And I use the term very loosely thinking what that person is thinking at that moment. And it's a lot of it is just a lot of it is utter, a lot of it is utter nonsense. And, you know,

Srini Rao

Yeah.

Srini Rao

Hahaha! Yeah.

Srini Rao

Totally.

Dan Pink

50 years especially, that's 25 years especially, is we've had a really explosion in very good research into human behavior. We know, we have so much more to know. But we know a lot now, and we can use some of those insights and apply them to work smarter and live better, especially if we recognize that it's a little complicated. There's nuance, you know? So let's go back to the motivation discussion.

I never say in the book that extrinsic motivation is inherently bad or that it never works. That's nonsense. Of course it does. There's some uses for there's some there's some uses for that. I try to say very clearly that if then rewards can actually boost performance on a narrow range of tasks. I also say when it comes to money and like you got to pay people fairly. It's not like you can offer people intrinsic motivation and then you know and then you know.

cut their salaries and recompensate them in units of bliss. You know, that's bullshit. And so there's nuance in what the research tells us. And exactly as you're saying, there is nuance in the interaction of the person in the situation. And that's basically everything we know about human behavior suggests that things happen at the intersection, at the interplay of the person in the situation. And so if you neglect one, it's not gonna work very well.

Srini Rao

Yeah, exactly.

Srini Rao

Yeah, I mean, I remember seeing one of our iTunes reviews said there's no feel good fluff on this show. I was like, that is a supreme compliment. I was so happy to hear to read that. Whoops.

Dan Pink

It is. It is, but I think that actually, I mean, I would sort of wanna edit that or sort of respond to that person and say, lack of fluff should make you feel good. And again, like we sort of over-indexed on a certain very narrow notion of happiness where happiness is about being smiley all the time and bathing in rays of sunshine and skipping through a meadow. That's not what happiness is.

Srini Rao

Yeah.

Dan Pink

Happiness is something deeper. Happiness is about meaning. Happiness is about purpose. Happiness is about the love and connection to other people. And so when you remove the fluff, you remove the barriers to meaning and purpose and significance.

Srini Rao

Well, let's get into this whole concept of regret. And I think that one of the things I'd like for you to do is just for the sake of people here, I know you have written this in the book, is to define regret for people. As this, you know, you define it as sort of this gap between something that we wish we had done and something that happened, but can you clarify it for our listeners?

Dan Pink

Sure, the most important thing to understand is that regret is an emotion, and it's a negative emotion. It's emotion that makes us feel bad. And the way that it makes us feel bad is by it. We look backward on our lives and look at a decision we made, look at a decision we didn't make, look at a decision, an action we took, look at an action we didn't take and wish we had done things differently. And then we wonder whether had we done something differently, the present would be better than it is. So

So it's a negative emotion, but it requires incredible cognitive dexterity because you're traveling in time, you're negating what really happens, you're traveling back to the present, and you're seeing a reconfigured present based on the decisions you made in the reconfigured past. This is why, as we were talking earlier, this is why five-year-olds can't experience regret. It's why sociopaths don't experience regret. It's why people with brain damage don't experience regret. So it's cognitively sophisticated, but it's an emotion that makes us feel bad.

What's more, it's a very, so that's a different, what's more, it's our most common negative emotion. It's one of our most common emotions overall. And when you pair those two things together, A, it's aversive, it makes us feel bad. B, it's ubiquitous, it's everywhere. That's a puzzle, right? We're supposed to be pleasure seekers. What's going on here? We have one of our most common emotions is one we don't like. Why, why, why? And

To me the answer to that is relatively simple and straightforward but I've been trying to bash people over the head with it which is this, it's useful, that's why it exists, it helps us, it clarifies what we care about and instructs us what to do in the future.

Srini Rao

Well, let's get into the four categories of regrets, the first of which is foundation regrets. You say foundation regrets arise from our failures of foresight and conscientiousness. Like all deep structure regrets, they start with a choice. At some early moment, we face a series of decisions. One represents the path of the ant. These choices require short-term sacrifice, but in the service of a long-term payoff. The other choices represent the path of the grasshopper. This route demands little exertion or residuousness in the short run, but risks exacting a cost in the long run.

And now that I'm talking to you about this, it makes me think of my sort of post-business school life where I am looking back at the last 10 years prior where I've been fired from every job, thinking to myself, okay, if I make those same decisions, I'm gonna end up in the exact same place at 40 that I am at 30 living with my parents. On the flip side of that, I also had to sacrifice financial security to make that choice and to do this, which had its own cost, you know? To say, okay, you know what? I'm gonna forgo paying off student loan debt to...

Dan Pink

Mm-hmm.

Srini Rao

build something because honestly, I thought to myself, okay, if I get a job and get fired and get another job and get fired, I'm literally gonna spend the rest of my life servicing this debt. And I was like, okay, so that's what they're gonna write on my tombstone, he paid off his student loan debt. And so I was like, okay, fine, you know what? I think that honestly, I've probably done more for the world by creating the show than I ever would have by making some investment banker richer by paying off my debt. At the same time,

Dan Pink

Oh man, yeah.

Srini Rao

That's reality too. It's not, you know, something that I can ignore. So I guess the question is that, you know, when you have choices like that for foundational regrets, I don't regret the decision to start the show because if I hadn't, I wouldn't be talking to you today. And even if I went and got a job now, I would be a thousand times more effective because of everything I've learned from talking to people like you. So how do you actually

Dan Pink

Mm-hmm.

Srini Rao

look back and say, okay, was this a foundational regret or was it the right choice?

Dan Pink

Well, I'll tell you what I heard. And let me take a step back, is that these four regrets that we're talking about come from my analysis of, at the time, 15,000 regrets collected from well over 100 countries. We're now north of 18,000 regrets. And just to give your listeners some context, and what I found is that when you ask people what they regret, having them group it into categories like,

career, family, education, whatever, wasn't very instructive because there was something deeper going on beneath the surface. And so I actually think, so on this particular question, I think there's actually less of a tension or trade-off than we might think. The foundation regrets that people told me about, foundation regrets are if only I'd done the work, especially the financial regrets that people had. They were not about...

Dan Pink

starting a business versus getting a steady job and a steady paycheck. They were about spending too much and saving too little. That's almost all the financial regrets were about that. They're saying, oh my gosh, like I had money and I squandered it on restaurant meals and cars and other things that I fundamentally don't care about a year later. That's a huge mistake. I regret that. If I could go back and change that, I would. They regret not starting saving earlier because they got

Srini Rao

Yeah.

Dan Pink

It took them later in their lives to understand the power of compounding interest. They don't like debt, especially if it's debt for things that don't matter. There are some people out there who regret taking on student debt, student loan debt, particularly if they ended up choosing a profession that they didn't end up pursuing.

Srini Rao

bright.

Dan Pink

And they're like, oh crap, I screwed that up. But most of the financial regrets, most of the foundation regrets are these regrets, as you say earlier, about prudence. It's about spending too much and saving too little. There's something, there's sometimes about health prudence. So I didn't take care of my body. I didn't exercise. I ate like crap for 10 years. They are regrets. We have outside of the United States, especially huge numbers of regrets about smoking. There also are regrets, amazingly, about, you know,

You know, it's like this is going back to your parents and all Indian parents. It's like a lot of people regret not listening to their parents and not working hard enough in school, you know, um, and, and because that somehow gave them this wobbly platform. So that's what foundation regrets are. If only I, if only I'd done the work. Um, you have very few people who, to the next category, and I'll make this connection here, the next category are boldness regrets, which are, if only I take in the chance.

Srini Rao

Mm-hmm.

Dan Pink

And these are regrets against spanning domains. There are regrets about travel. There are regrets about not asking people out on dates. There are regrets about not starting businesses. And it is very few people have foundation regrets because they have boldness regrets. I guess that's what I'm trying to say. Because they acted boldly. Very few people have foundation regrets because they acted boldly. They have foundation regrets because they didn't act.

Srini Rao

Mm. Yeah.

Dan Pink

at an earlier point in their life. You have very few people who say, oh my God, you have few who say, oh, I really messed up, I started a business and it went under and I should have just taken a steady job. You have some of those. But for every one or two of those, you have literally, I mean, I'm not joking, 35, 40 people with the opposite regret.

Srini Rao

Yeah, okay. So one of the things you say about boldness regrets is that at the heart of all boldness regrets is a thwarted possibility of growth, the failure to become the person happier, braver, more evolved one could have been the failure to accomplish a few important goals within the limited span of a single life. And you say with boldness, regress, the human need is growth to expand as a person to enjoy the richness of the world, to experience more than an ordinary life. The lesson is plain speak up, ask him out, take that trip, start that business, step off the train. And I

wanted you to share the story of stepping off the train with our listeners because that was probably my favorite part of the book. Yeah.

Dan Pink

Oh really, interesting. Okay, so this is a story about, this is a, so again, one of the interesting things about, you know, how do you fashion this, how do you fashion this, how do you investigate these ideas? And especially on this one where I just had an itch that this was something that I was curious about and I wanted to try to make sense of it. So we talked about, I did the academic research.

looked at the academic research, I did my own public opinion survey, which yielded some, but not a huge number of insights. And then this massive collection of regrets from all over the world proved to be this incredible breathtaking trope. And one of the people who submitted a regret was a guy named Bruce. And as I heard his story, and I ended up interviewing him a few times and wrote about him in the book, then basically here's Bruce's story. So he graduated from college, it's the early 1980s. He's working in Sweden as a...

on a farm somewhere in Sweden. He, single American guy, 23 years old, 20, and he says, I'm gonna travel around Europe, so he gets a U-rail pass. He's riding on a train one night, and he's in France, and there's a seat open next to him. The train stops in France, and a young woman gets on the train and sits in the empty seat next to him. And they, she's Belgian, she's working as an au pair in France, they start talking, they're talking in English because his French isn't very good.

and they start laughing, they start playing games, word games, they start holding hands, and Bruce is just amazed. It's this magical experience. Like he's met his, he didn't use this word, but like his soulmate has just wandered onto the train and taking the seat next to him. It's like within, within like literally like a couple hours, it was like they were a couple. I mean, it's bizarre and incredible, breathtaking.

And so she, the train's rumbling along and it gets to Belgium and she says, this is my stop. And so Bruce is like thrown from his reverie. And she says, this is my stop. He said, I'll come with you. And she says, oh my God, my father would kill me. So Bruce doesn't know what to do. The train's like literally pulling into the station. And so again, it's pre-internet time. It's pre-internet day. So she can't say, hey, check out my LinkedIn profile. Instead, he just, he scribbles his mother's mailing address in Texas of all places.

Dan Pink

on a piece of paper, hands it to her, they kiss and she and the doors open and she leaves and Bruce 40 years later said submits this thing he said I never saw her again and I've always wished I stepped off the train and that regret embodies a lot of people's regrets that is I mean not to oversell the metaphor here but

People regret not stepping off the train. And what's interesting when you talk to this guy, Bruce, and he is one of the few people who didn't want me to use his full name in this book. And so I only have to use his first name. But when you talk to Bruce, what, he's not saying, oh my God, if I had stepped off the train, I would be a, you know, a top executive at a Belgian company.

I would have this passel of Belgian American kids who were trilingual and gorgeous. He's not saying that. What bugs him is that he had a moment in his life when he could have been bold and he didn't do it. And he's nagged by that what if.

Srini Rao

Hmm. Well, let's do this. I know you did your person in a different order. You went to moral regrets third, but I want to go to connection regrets and then we'll wrap up with more regrets. You say that connection regrets are the largest category in the deep structure of human regret. They arise from relationships that have come undone or that remain incomplete. These types of relationships that produce these regrets vary spouses, partners, parents, children, siblings, friends.

Dan Pink

That's fine.

Srini Rao

colleagues, the nature of the rupture also varies. Some relationships fray, others rip, a few are inadequately stitched from the beginning. Then you go on to talk about rifts and drifts. And you say that rifts usually began with a catalyzing incident, an insult to disclosure or a betrayal. And you say that drifts follow a muddier narrative. They often lack a discernible beginning, middle or end. They happen almost imperceptibly. One day the connection exists, another day we look up and it's gone. And...

I wanted to pull a clip from one of our previous episodes with Lydia Denworth. Take a listen because I think it'll make a perfect jump off point to talk about connection regrets.

Srini Rao

So I thought that was a fitting way to kick off our conversation about sort of drifts and rifts. I don't think that that's about rifts per se, but I do think it actually accurately describes drifts. But let's start with both because I think that with age, I've started to really kind of look at this, particularly in terms of family in a very different way.

Dan Pink

Mm-hmm. No.

Dan Pink

In one way.

Srini Rao

Well, you know, I remember we had Frank Ostasevsky from the Zen Hospice Project here, and I remember telling him, I said, Frank, like I used to be afraid of ending up alone and now I'm actually terrified that one or both of my parents is going to die before I get married or have kids. And he said, yeah. He said, well, he said, you have no idea when that's going to be. He said, so spend time with them now. I literally have the clip, you know, I mean, I've played it before on the show, so I don't want to do it again. Um, but it, it just struck me that was so important. And I remember right after that, I started going home to my parents'

Dan Pink

Tough.

Srini Rao

every Sunday for dinner when I lived in California. Um, and when my sister got married, I was the only one who was not supposed to go on the trip to India with my parents. And she was like, I think you're going to regret it. If you don't come on this trip, this is, you know, we haven't been together in 25 years and she's like, and I'm pretty sure this is the last time that we're ever going to get to do this. And she paid off a credit card for me. I cashed in the miles and I went. And honestly, that was the best addition I made because my grandmother died, uh, last year and I realized my sister was spot on. That was it. Like I knew we would never take it.

Dan Pink

Mmm.

Dan Pink

Wow. Oh my gosh.

Srini Rao

right that would be the last time we would ever go. All together.

Dan Pink

Yeah, I mean, I think that's very good decision making, very good way to reckon with anticipated regrets. And I think that on the clip, there are a couple of interesting things about it. Number one is that she was literally describing, as you say, drifts. And rifts are way more dramatic, but way less common. That the way that a lot of these relationships come apart is profoundly undramatic. They just kind of...

Drift apart exactly as she's saying. Now, there's some cases where you drift apart and it doesn't bug you that much. That's happened to me and that's fine. That's okay. There is, as she's suggesting, a kind of a pruning of our friendships that is very healthy. But there are some when you drift apart, it does bug you. It does give you that stab of regret. And that's a signal that is telling you something. That's telling you that...

The relationship is valuable. And what I found in talking to all these people is that the barrier to reaching out was twofold. Awkwardness, oh, it's going to be so awkward if I reach out. And second, that the other side's not going to care. And this is an area where we are, both of those areas, we are dead wrong. It's always less awkward than we think, not nearly as awkward as we think.

And in most cases, not every single one, but I'm convinced 19 out of 20, 49 out of 50, the other side does care. And so to me, if you're at a juncture and you're wondering, should I reach out, you've answered the question, you should. You should reach out. Pick up the phone, reach out. If you don't, and the worst thing that can happen is you reach out and you are the one out of 50 where the person says, ah, I don't wanna hear from you. Fine, you're done.

But what really nags people are these relationships that drift apart and they don't do anything. And then in some cases, as you averted with your grandmother, in some cases it's too late. The door closes because someone passes away.

Dan Pink

I mean, for me, one of the big lessons personally from this book is, as someone who's not great at reaching out, is exactly that. When in doubt, reach out. Always reach out. Always go to the funeral. I mean, if you get nothing else out of reading this book and you redirect your life a little bit more in that direction, I feel like I've done a service to humanity.

Srini Rao

Let's finish by talking about.

two things, moral regrets and the regret optimization framework. Let's start with moral regrets because I think that moral regrets, as you pointed out, are the smallest of the category, uh, representing only about 10% of the structure. And yet for many of us, these ache, the regret, ache regrets most, last the longest. And, you know, like I can't help, but think about, you know, friendships that have ended in the wake of, of building this business, you know, and often sometimes choosing.

the success of the business over the friendship because it was what was right for the business and I still to this day don't feel good about any of those situations.

Dan Pink

Hmm.

Dan Pink

Yeah, but did you do the wrong thing at that time? Yeah, I don't think so. Yeah, I think that, you know, with moral regrets, it's pretty clear that people regret. They're not regretting the bad outcome. They're regretting that they were at a juncture where they could do the right thing and do the wrong thing and they do the wrong thing. So these moral regrets are, I mean, the two biggest varieties are regrets about bullying earlier in life.

Srini Rao

No, I don't think so because that's the thing, right?

Dan Pink

also regrets about marital infidelity. And those are two things that I think that most of us, not everybody, but most of us, there's a rough consensus that yeah, that's probably not a good idea. That's probably the wrong thing to do. But when you make other kinds of choices in life that sometimes have consequences that aren't great for other people, I'm not sure that's necessarily a moral rule.

Srini Rao

Yeah. Well, you know, it's funny when I reread that part on bullying as I was capturing the notes this morning, I couldn't help but think of this memory of a kid that I became friends with in the fifth grade, was, you know, kind of nerdy and goofy and he liked the Beatles and, you know, we were becoming good friends and we stopped being friends because other kids didn't think he was cool. And of course, nobody thought I was cool either. But the fact that that, you know, influenced my decision is one of those things I was like, OK, that probably falls in the category of a moral regret.

Dan Pink

Yeah.

Dan Pink

Yeah, I think so. I think it does. It's interesting. And that is a kind of regret that I wish I had explored a little bit more because I have some regrets kind of like that in that, to me, that's a regret about the moral value of kindness in a way. And we can be unkind through action, which that's bullying. I think that's fairly common. But for me, some of my biggest regrets are regrets about kindness through inaction. So I...

as a younger person, you know, in school and in college as a young professional, I was never a bully. I never bullied anybody. And yet I was in situations where people were being excluded, like, like your nerdy friend, where people were being left out. I saw it happening. I knew that it was wrong. It's not like, oh, I was confused. I knew it was wrong at the time. And I didn't do a damn thing. And that really bothers me.

Srini Rao

Yeah.

Dan Pink

And that is a moral regret. Now, once again, circling back to what we were talking about earlier, the question is, so I'm experiencing this negative emotion. What do I do with that negative emotion? I can say, no regrets, and go out and get a tattoo that says that because I never look backward. I can ignore it. I can also go the other direction and say, oh my gosh, I am the worst person in the world. I am so deeply unkind. I am a menace. And just spin myself into a downward spiral of rumination.

That's really bad too. Or I can simply think, I can say, wow, here's a negative emotion coming in. This is a signal, this is a message. This is telling me something. And what it's telling me, again, going back to these two verbs, it is clarifying something for me. It's clarifying what I value, which is that I actually value kindness. And this helped me realize that. Second, it is instructing me what to do. Be kinder. And I found myself

in grappling with this regret, not ignoring it, not getting hobbled by it, that, I mean, this is small, but if I'm, say, at a social gathering and there's a cluster of people talking together and I see somebody who is, you know, several steps away but isn't part of any conversation, I will affirmatively bring them in. And I would not have done that before unless I had reckoned with this regret.

Srini Rao

Yeah. Well, let's finish this up by talking about the regret optimization framework. I love that you kind of dissected Jeff Bezos' regret minimization frame. You say that our goal should not always be to minimize regret. Our goal should be to optimize it. The regret optimization framework holds that we should devote time and effort to anticipate the four core regrets, foundation regrets, boldness regrets, moral regrets, and connection regrets. But anticipating regrets outside of these four categories is usually not worthwhile.

Dan Pink

Yeah, and so the weird thing is it's a little bit hard to under, it's a little bit paradoxical, but the regret minimization, the idea that we should minimize all of our regrets is a form of unhealthy maximization. And what we know is when we, and this is, you know, social psychology 101, when we make decisions, we have, in some sense, two choices. We can maximize every decision. We can maximize the decision or we can satisfy the decision. So we can say, what am I going to have to dinner tonight? I'm here in Chicago. I'm going to have the best hamburger there is in Chicago.</ p>

I have to get my roof repaired in my house. I'm going to find the best roofer in the Delmarva area. And you can try to maximize every day. What shirt should I wear today? I'm going to find the best shirt I can wear today. The research tells us very clear is that maximizers are miserable because there's always more to do that you can always do a little bit better and that satisficers are surprisingly happy. My view is that...

what we should be doing is we should be maximizing, when we think about our regrets in the future, we should be maximizing the choices to avert those regrets and just satisfies everything else. So if you think about it this way, if you're making a phone call to the U of 2032, the U of 2032 is not gonna give a damn about whether you had a hamburger or an impossible burger or...

Turkey Tetrazzini last night. All right, the U of 2032 is not gonna care whether you bought a blue car or a gray car, trust me. But the U of 2032 is gonna care if you had a chance to do something bold and instead you chickened out and played it safe. The U of 2032 is probably gonna regret that. The U of 2032 is gonna regret, likely, that if you right now can do the right thing or do the wrong thing and you do the wrong thing. The U of 2032 is...

Srini Rao

Yeah.

Dan Pink

going to say, Jesus, come on, what's wrong with you? You had this friend who you drifted apart and now you drifted apart even 10 years later, it's going to be even harder to restore that connection but it's obviously meaningful to you. So what we should be doing is satisfying on most decisions but maximizing on avoiding regrets in these four areas because we know that these four areas are what give our life meaning and purpose and shape.

Srini Rao

Wow, this has been absolutely incredible, Dan. It is such a pleasure to talk to you. I have one final question for you, which is how we finish all of our interviews on the unmistakable creative. What do you think it is that makes somebody or something unmistakable?

Dan Pink

Yes, sir.

Dan Pink

I think it's the willingness to go in one's own direction, even irrespective of what anyone else says.

I really do. That is, I think that, and I'm sort of saying that to myself in a way, and that I think that we're too, not as praise, but as guidance, that we're too affected by other people's opinions of us and we care too much about what they think of us when in fact they're not thinking of us, they're thinking of themselves. And so I think that what makes somebody unmistakable is that ability to stick with their vision

Srini Rao

beautiful.

Srini Rao

Ha ha ha.

Dan Pink

criticism and other people saying, what the hell are you doing?

Srini Rao

Well, I can't thank you enough for taking the time to join us and share your story, your wisdom, and your insights with our listeners. Where can people find out more about you, your work, the new book, and everything that you're up to?

Dan Pink

You can find out everything you could possibly want to know at danpink.com. We've got a newsletter, we've got resources, there's information about books, there's all kinds of groovy stuff.

Srini Rao

Beautiful and for everybody listening we will wrap the show with that.