Best of 2022: Dan Pink | The Power of Regret

Srini: Dan, welcome to Unmistakable Creative. Thanks so much for taking the time to join us. Thank you!

Dan Pink: Wow. It was such an interesting question because I had never thought about that before, and there might be, might, might, might be a retrospect of revelation here. So, on the two parts, the first one was 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.

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

Srini: 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, it seems to be a deep amount of research and conversations with people that go into it. I watched your TED Talks and 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 I developed those kinds of social skills after that. I don't think I, you know, and I don't think that's unusual for adolescents not to have great social skills. I think 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 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 how I'm wired. And I think that none of that said, I do think that I've developed a little bit of what you might think of as bilingualism. And then I can actually cross the border and speak another language and talk to people and I enjoy it, you know, and I enjoy doing that, but I think my natural state is alone. Yeah.

Srini: 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 the drive where you said, "In a moment of youthful indiscretion, I decided to go to law school."

Dan Pink: I wonder, forgive me for laughing at my own joke, but it's pretty funny. Yeah. Well, I

Srini: I, 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. So but I wonder what kind of guidance did your parents give you in terms of career paths? Because, you know, when you grew up in an Indian family, there's sort of this clear, you can be any kind of doctor, lawyer, engineer, you want to be narrative.

Dan Pink: Yeah. It's similar to that. I mean, I think that there's a, there's you know I think that there, that 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's driving 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 stereotype, but many people in the kinds of cohorts we're talking about, tend to be then, you know, if you were good at, if you were good at math and science, you could, you know, become a lawyer, a doctor, or maybe an engineer. I think doctors had a higher status than engineers in many of these groups. Yeah. And then and then if you were a kid like me who was fairly facile with words, you could become a lawyer. And. And that was, and those were the those are

Srini: 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, I would have gone to UCLA instead. I remember my high school band director telling me, he said, "You're going to give up girls sunbathing on lawns to go to Berkeley." And I thought to myself, "You know, the weather sucks here. The city is kind of a dump the first time I saw it." And it's funny because I don't remember having the greatest time, but I do have fond memories of the place. But I don't remember being particularly happy while I was there. This raises this question, you know, to go back to your earlier point about this idea of autonomy, purpose, and mastery. And I feel like those things are so left out of our education system. Yeah. 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 the research that you did around all of this. I mean, I think it

Dan Pink: 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 this. I don't think that there's a simple solution for this at all.

I think that there might be a set of design principles that could be useful, among them is, is to give, there isn't a huge amount of autonomy in, especially in elementary and secondary education. And in fact, what often rewards those systems often the reward is not intellectual engagement or creativity, or even excellence. What it rewards is compliance. What it rewards is 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, as 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 engaging. And the reason for that is that it's a system built to, it's a system built on control and control leads inevitably only to those two kinds of behaviors

Srini: Well, you're preaching to the choir. I mean, yeah. As a Berkeley undergrad, I completely agree. People brag about the number of Nobel laureates. And my dad, who's a professor, is like, yeah, just pick us somebody as a Nobel Laureate. It doesn't mean that they teach. In fact, many of the Nobel laureates are the worst teachers. But it's interesting you bring up arts education because I spent 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 they have are football teams. So naturally, that's a byproduct, but I will tell you to this day that hands down one of the greatest gifts I ever got from my time in Texas was an incredible music teacher who actually taught me how to practice, how to get better at things, and cultural aptitude.

Dan Pink: For me, I mean, that's the thing about the arts, it's like we have clues about not only a reconfiguration but also from our experiences there. So, one of the things that really take me, and as you can tell from talking to me, that list is extraordinarily long. One of the things that, well...

Srini: Yeah, trust me. I asked the question for a reason. I, yeah.

Dan Pink: You certainly the person who started this conversation certainly poked it. Here, it sort of irritates me when people say, especially about adolescents and high schoolers, "Oh, they're not motivated." They're not motivated. Do you know? Cause they, you know, write a book about motivation or people ask 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, and, and you know, my view is like, "Oh, well they think that your incredibly boring and controlling classroom sucks. And I don't blame them, but let me show you where they're motivated." Have you seen them in the 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 engage? 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 in the school newspaper. It's your choice. Second

Srini: Yeah, well, you know, I can't help but think a bit about intrinsic motivation because I'll tell you one thing, 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 $5 every day. You come home and have that conversation with your Indian parents, that's 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 thirty-plus year later, it was like he was teaching us the power of intrinsic motivation. Granted, you know, we weren't motivated to get good grades intrinsically, but it played out later in life. So one thing, knowing what you do, you mentioned that you're a parent. What 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

Dan Pink: Make. 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 are right now. I mean, my kids have already graduated from college and I have another kid who is, who is in college. So they are, they are well on their way. And, I think that what my wife and I tried to do was really be is, is be humble about as much as we can. About what we know, what we knew and what we could influence, and what we didn't. So I think that I think that beginning it from a place of humility is really important. I think that it's what's really important to the square is to, is to combine both sorts of high expectations and support. And what that means is you have parents who 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 want to do is

Srini: Well, it's funny 'cause I'm not a parent. And I ask all these questions about parenting. 'Cause we have a lot of parents who listen, and I, you know, I have this misguided idea that I'm gonna 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 gonna screw you up, and your job is to fix everything we screwed up in therapy."

Dan Pink: 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. Yeah.

Srini: Easier said than done. Probably. Yeah. So one more question about this. What do I think will make a perfect segue into talking about the book? 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, purpose, and mastery. In most organizations, we hire for compliance and 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 I graduated from business school in April 2009, 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 waits 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 strength and put somebody in a job where 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 improvement plans like these don't

Dan Pink: I know that's their only purpose. That's their only purpose; they are exactly. That's it? I mean, performance improvement plans are a joke. They're basic; they're litigation insurance. 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: Oh, it was not a subtle signal at all. For me, the minute I heard those words, I was like, "All right, I've got three weeks to find a new gig."

Dan Pink: Yeah!

Srini: So how do you change that in an organization? Because like, you know, I think, as 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. For now, if I went into a job interview and I got a bad feeling, I remember very distinctly interviewing this guy. At some point, 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 eight o'clock, we mean eight o'clock, not eight fifteen." And I remember thinking to myself, if I had the guts I do now, I would have looked at everybody in that room and said, "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: Months later. Yeah. Yeah. Yeah, I mean, I wish that would be very cinematic to do that this year. Yeah, I mean, so I guess the question is, is, why, and yeah, and I think that the answer is, it's interesting. I'm not sure. I think it's a super, I think it's a really, really interesting, really interesting question and, 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 and compliance actually led to efficiency. But now a lot of those routine algorithmic tasks are actually being done by software or machines. And so what people are doing more and more is tasks that require more judgment, creativity, and discernment. Hmm. As a consequence. And, and, and, but, but our organizations still have the legacy of that old way of doing things and they haven't shaken that up. I think that's one thing. The second thing is that I think that managers for a long time have been thinking

Srini: Hmm. Wow. Well, I think that that makes a perfect segue into talking about the power of regret. I have one question for you. What was it that led to you writing this book? Like, why was this the sort of natural follow-up to Sell Is Human?

And one of the other things I've always admired about your books is that they're easy to read. I know that a lot of work goes into them, but I find your books are a breeze. 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 make them accessible to the average person. So, talk to me a little bit. I really...

Dan Pink: I really appreciate your 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, I really appreciate it. But it's a product that is a product of a lot. Okay. So, so let's go to, so, so we'll, we'll come back and talk about why my midlife crisis led to a book about regret in a moment, but for now, the process is, well, it takes me a very long time. It takes me a very, very long time to write books. And essentially what I do is I 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 in the research. I begin to see in my mind's eye, the structure of the book. And for me, again, your mileage may vary, but for me, the structure is everything. If I can figure out the structure of the book in my head, it's an order of magnitude easier. And so

Srini: I love it. I

Dan Pink: Yeah, I mean, it's about the structure and making sure that every element fits together. And one of the things that bug me as a reader is the amount of filler in some of these books. Let me give you an example from the regret book. I did probably a month's worth of research, looking at how regret develops in kids, and at what point it could be because regret is such a sophisticated way of thinking. It's a combination of emotion and cognition, and little kids can't do it. Your brain has to develop past a certain point to process regret. So I spent a month looking at it. But then when I started writing about it, I was like, "Shoot, there's really just one thing to say here. And this month of research is probably two paragraphs." That's a bummer, but it would be worse if I torture readers by giving them nine pages of it just because I found it out. So that's that.

Srini: 'Cause I can't help but think of Steven Pressfield's books. I'll 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 Steven 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 was like, "There isn't one." I'm 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. And what unlocked that for me was something Jennifer Loudon told me: she said, "Your structure has to be linear. Your process doesn't."

Dan Pink: Change everything. That's a great way to, that's a great way to. That is, that's a, 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 that's, that's, that's exactly. That's a really, 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've found a little, maybe a, perhaps 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, as a writer, you are asking the thing of your readers: an extraordinary request. 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

Srini: Yeah. Well, speaking of a book that has met that bar and one that I don't regret spending my time on, let's talk about yours. Now that I've talked your ear off about everything other than the book.

Dan Pink: No, I'm happy. I'll talk about, I'll talk about, you know, again, it's your show, so I'll talk about anything. I'll tell you about anything.

Dan Pink: Too. I have a lot to talk about. I'll talk about, I'll talk about the dating show that you were on too. If you want to talk about that.

Srini: Want to go into the bookstore?

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

Dan Pink: It was, you know, I'm about 10 years older than you. And so you might not have had this jarring experience yet, but you will, young man, trust me, you will, you will, at some point realize that through no fault of your own, you have mileage on you. And when you look back, there's a room there. When you go to an online form to put in your birth date, and your birth year, suddenly you're scrolling much more than you ever did.

And I already feel like that. And, and, and there's, and that's kind of alarming to look back and say, wow, I got some mileage on me, but at the same time, in my age, in my fifties, I feel, I mean, I hope that I have some mileage ahead of me and, and I want to be able to, and I want to, so you have this passage of time and you want to say, I don't want to throw away my shot. 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 you know, also one of my daughters graduated from college and that was

Srini: Yeah. Well, I think I have to agree with that. Well, so one of the things you opened the book by saying is that regret is not dangerous or an abnormal deviation from the steady path to happiness, it's healthy and universal. An integral part of being human, its progress is also valuable. It clarifies, instructs, and doesn't just drag us down and 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. So, why is it that, you know, the sort of, you know, popular platitude narrative is live without 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. We are over-indexed on positive, but we, especially Americans, are over-indexed on positive. And we've been taught somehow that you should always be positive. You should always think positively, you should banish the negative, and you should always look forward and never look backward. And here's the thing, 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 want to have positive emotions. There are benefits to optimism. You want to have more positive emotions than negative emotions. But the thing is we've gone too far and said that you should only have positive emotions and that negative emotions, particularly our most common negative emotion, regret, are somehow dangerous that it weakens you. So I think that's, 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

Srini: Yeah, it's funny because I, you know, 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, you know, 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 culpable for is ignoring context where it's like, you know, hey, here's this blanket formula 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: Yes. Yeah. Yeah. And, and, you know, again, you know, a lot of the stuff in the self-help literature isn't rooted in anything. Yeah. 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 a lot of it is just utter nonsense. And what we've had in the last 50, especially the last 25 years, is we've had a really an 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 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 are 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, you got to pay people fairly. It's not

Srini: Yeah. I mean, I remember seeing one of our iTunes reviews that said, "There's no feel-good fluff on this show." And I was like, "That is the supreme compliment!" I was so happy to hear/read that.

Dan Pink: But I think, I think that actually, I mean, I would sort of want to edit that or sort of respond to that person and say lack of fluff should make you feel good. That, and again, like, like 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. Happiness is something deeper. Happiness is about meaning. Happiness is about purpose. Happiness is about love and connection to other people. And so when you remove the fluff, you remove the barriers to meaning and purpose. Yeah

Srini: Well, let's get into this whole concept of regret. And, you know, 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. I, you know, you define it as sort of this gap between something we wish we had done and something that happened, but can you clarify it for our

Dan Pink: Listeners? Sure. The most important thing to understand is that regret is an emotion and it's a negative emotion; it's an emotion that makes us feel bad. And the way that it makes us feel bad is by it, it [making us] look backward at our lives and [at] a decision we made, [at] the decision we didn't make, [at] a decision and action we took, [at] an action we didn't take, and [we] 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, it's a negative emotion, but it requires incredible cognitive dexterity because you're traveling, you're negating what really happened. 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 about earlier, this is why five-year-olds can't experience regret. It's why sociopaths don't experience regret, why people with brain damage don't experience regret. And so it's cognitively sophisticated, but it's an emotion that makes us feel bad. What's more

Srini: Yeah. Well, let's get into the four categories of regrets. The first of which is the foundation or foundational regrets. These 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, that 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 as in us 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 going to 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 had to sacrifice financial security to make that choice and do this, which had its own cost. You know, to say, okay, you know

Dan Pink: Well, I'll tell you what I heard, and let, let me, let me take a step back. These, these four regrets that we're talking about come from my analysis of, at the time 15,000 regrets collected from, well over a hundred countries; we're now north of 18,000 regrets. And just to give your listeners some context. 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. So I actually think so. So on this particular question, I think there's actually less of a tension or tradeoff than we might think. The foundation regrets that people told me about were if only I'd done the work, especially the financial regrets that people had; they were not about starting a business versus getting a steady job and a steady paycheck. They were about spending too much and saving too little—that's all the financial regrets were about. 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

Srini: Yeah. Okay. So one of the things you say about boldness regrets is that at the heart of all boldness is regret as a third possibility of growth. The failure to become the person happier, braver and bolder could have been the failure to accomplish a few important goals within the limited span of a single life. And you say with boldness or aggression, the human need is growth to expand as a person to enjoy the richness of the world to experience more than ordinary life. The lesson is plain. Speak up, ask about, take that trip, start that business, and step off the train. And I wanted you to share the story of stepping off the train with us because that was probably my favorite part of the

Dan Pink: Interesting. Okay. So this is a story about, this is a so so, so again one of the interesting things about. You know, how do you, 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 I was curious about and wanted to try to make sense of it.

So we talked about it, and I did the academic research. What did the academic research yield? 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 trove. And one of the people who submitted a regret was a guy named Bruce, and as I heard his story I ended up interviewing him a few times and wrote about him in the book. Then basically here's the story.

So he graduated from college. It's the early 1980s. He's working in Sweden a, as an au pair somewhere in Sweden. He's a single American guy, 23 years old, in his 20s. And he says, I'm going to travel around Europe, so he gets a Eurail pass. He's riding on a train one

Srini: Well, let's do this. I know you did your personal in a different order. You went to Marlo Gretz third, but I want to go to connect some 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 regrets. They arise from relationships that have come undone or that remain incomplete. These types of relationships produce these regrets: very spouses, partners, parents, children, siblings, friends, and colleagues. The nature of the rupture also varies; some relationships fray and others rip. A few were inadequately stitched from the beginning.

And then you go on to talk about rifts and drifts. You say that rifts usually begin with a catalyzing incident: an insult, a 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.

I wanted to pull a clip from one of our previous episodes with Lydia Denworth. Take a listen, because I think it'll be the perfect jump-off point to talk

Dan Pink: It's much harder to maintain a relationship when people move further apart, but it's not impossible. So it really depends on motivation and, how much it matters. And I think what does happen is people get busy and get caught up with the new people in their life or their work. And the longer it goes without seeing someone, the less connected they feel and the less they know of the day-to-day of that person's life. That's natural and it's not the end of the world. This is important. So when you said it didn't feel reciprocated in the same way, that's the critical juncture when you can say to yourself, "Maybe this friendship isn't sustaining me in the same way and I'm going to let it go or I'm going to shuffle it."

The analogy I like to use is that if you think of your friends as concentric circles, the people closest to you, and then a little further out, a little further out, when you have a friend like that, it doesn't mean you have to not be friends with them anymore, but you can shuffle the furniture of your friendship to an outer room. Right?

Srini: So I thought that that was a fitting way to kick off our conversation about drifts and rifts. I don't think that that's about rifts per se. Do you think it actually accurately describes drifts, but let's, 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: In what way?

Srini: Well, you know, I remember we had Frank Ostaseski from the Zen Hospice Project here. I remember telling him, I said, "Franklin, 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. Will I get married or have kids?" And he said, yeah, he said, "Well, you have no idea when that's going to be, so spend time with them."

Now I literally have the clip. Do you know what I mean? I've played it before on the show. So I don't want to do it again. But it, it, it just struck me that that was so important. And I remember right after that, I started going home to my parent's house every Sunday for dinner when I lived in California.

And one of my sisters 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 I'm pretty sure this is the last time

Dan Pink: Yeah. I mean, I think that's, that's very good. Decision-making is a very good way to reckon with, and anticipate regrets. And I think that in the clip, there are a couple of interesting things about it. Number one is that she was describing, as you say, drifts and riffs are way more dramatic, but way less common; the way that a lot of these relationships come apart is profoundly undramatic. It just kind of drifts apart. Exactly, as she was saying, now there are some cases where you drift apart and it doesn't bug you—that has happened to me and that's fine, that's okay.

There is, as she was suggesting, a kind of pruning of our friendships that is very healthy, but there are where, 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—it'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—ugh, it's going to be so awkward if I reach out—and second, that the

Srini: 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, representing only about 10% of the structure. And yet, for many of us, these are the regrets that last the longest. And you know, I can't help but think about friendships that have ended in the wake of building this business, and oftentimes 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: Yeah. But do you do the wrong thing at that time?

Srini: No, I don't think so. That's the thing, right?

Dan Pink: Yeah. I think that I, you know, with more regrets, it's, it's, it's pretty clear that people remember. They're not preventing a 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, so these more regrets are, I mean, the two biggest varieties are regrets about bullying earlier in life and 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, that's probably not a good idea. That's probably the wrong thing to do. But when, 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 regret.

Srini: Well, you know, it's funny when, when I re-read that part on bullying as I was taking 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. He was 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 influenced my decision is one of those things that I was like, okay, that probably falls into the category of a moral regret.

Dan Pink: 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 like that, that, to me, that's a regret about the moral value of kindness in a way. And we can be unkind through action, which is bullying. I think that's fairly common, but for me, some of my biggest regrets are regrets about kindness through inaction. So, as a younger person, in school, in college, and as a young professional, I was never a bully. I never belittled anyone. And yet, I was in situations where people were being excluded, like your nerdy friend, where people were being left out. I saw it happening. I knew that it was wrong. I wasn't confused - I knew it was wrong at the time. And I didn't do a damn thing. And that really bothers me. And that is moral grit. 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

Srini: Well, let's finish this up by talking about their grit optimization framework. I love that you kind of dissected Jeff Bezos's regret minimization framework, where you say that our goal should not always be to minimize regret, but rather to optimize it.

The regret optimization framework holds that we should devote time and effort to anticipate the four core regrets: foundation regrets, boldness, or guts, 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 understand, it's a little bit paradoxical, but then, the regret minimization, the idea that we should minimize all of our regrets is a form of unhealthy maximization. And what we know is that when we, when we, and this is, you know, psychology 101, when we make decisions, we have, 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 for dinner tonight here in Chicago, I'm going to have the best hamburger there is in Chicago. You know, I have to get my roof repaired on my house. I'm going to find the best roofer in the Delmarva area. You know and you can try to maximize every decision. What, shirt should I wear today? I'm going to find the best shirt I can wear today. What the research tells us very clearly is that maximization makes us miserable because there's always more to do. You can always do a little bit better, and satisfaction makes us surprisingly happy. My view is that what

Srini: Yeah, well this has been absolutely incredible, Dan. It is such a pleasure to talk to you. I have one final question for you: How do we finish all of our interviews on Unmistakable Creative? What do you think it is that makes somebody or something unmistakable?

Dan Pink: I think it's the willingness to go in one's own direction, even in the face of respectability. Anyone else says, "Oh, I really shouldn't do that." That is, that is I think that and I'm sort of saying that to myself in a way that I think that we're, 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 and do things that are unconventional even in the face of criticism and other people saying, "What the hell are you doing?"

Srini: Beautiful. Well, I can't thank you enough for taking the time to join us and share your story, your wisdom, and your insights. A lot of listeners, where can people find out more about you, your work, the new book, and everything that you're up to?

Dan Pink: And find out everything you could possibly want to know at danpink.com. Danpink.com has a newsletter, resources, information about books, and all kinds of groovy stuff.

Srini: Beautiful. And for everybody listening, we'll wrap the show with that.