Regret. We’re told to banish it. To never look back. But what if that’s all wrong?
In this rich, eye-opening conversation, I sit down with longtime friend and bestselling author Daniel Pink to explore the surprising truth about regret, and how it can actually become a powerful compass for a more meaningful, connected, and satisfying life. Dan’s book, The Power of Regret: How Looking Backward Moves Us Forward, draws on deep research across psychology, neuroscience, and more—including a global survey of 16,000 people—to reframe this misunderstood emotion.
We explore:
- Why regret may be the most valuable negative emotion we experience
- The 4 core types of regret and what they reveal about what really matters
- How to use regret to make better decisions, build stronger relationships, and live with intention
- A simple 3-step process to transform regret into clarity and forward movement
- The difference between regret and disappointment, and why agency matters
If you’ve ever looked back and thought, If only…, this episode offers both comfort and guidance. It’s not about getting stuck in the past. It’s about learning from it—so you can build a better future.
And along the way, Dan shares vulnerable moments from his own life, surprising insights from his research, and practical tools you can use right now.
This is one of those conversations that stays with you.
You can find Daniel at: Website | Instagram | Episode Transcript
If you LOVED this episode:
- You’ll also love the earlier conversation we had with Dan about the powerful role of timing in life.
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photo credit: Nina Subin
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Episode Transcript:
Dan Pink: [00:00:00] What I discovered, to my surprise, is that regret points the way to the good life. That regret teaches us about the good life in ways that almost no other topic does. I think that’s at the heart of why people are leaning in. If you look at people’s regrets, the guts of people’s regrets and synthesize them, analyze them, they tell you what makes life worth living.
Jonathan Fields: [00:00:22] So we’ve all been told, tried to live a life without regrets. But what if regret was actually a good thing? That is a highly provocative question that today’s guest, Dan Pink, asks, and then answers with a whole bunch of researched and validated ways that regret can actually be an incredibly valuable experience and even a power tool for a life well lived. In fact, a life entirely without regret, he argues, might even do more harm than good. I’ve known Dan for well over a decade now. He’s been on the show a number of times over the years. A former white House speechwriter, he left that world and shifted focus to writing books that really opened our eyes to the human condition and plant seeds to to do life better. These include New York Times bestsellers A Whole New Mind, Drive to Sell His Human, and When his books have sold millions of copies, been translated into 42 languages, and won many, many awards. And in Dan’s new book, The Power of Regret, he takes on this topic we’ve all grappled with and gives it this surprising reframe. He draws on research in psychology and neuroscience, economics and biology to challenge widely held assumptions about emotions and behavior, and using the largest sampling of American attitudes about regret ever conducted, as well as his own World Regret survey, which, by the way, has collected regrets from more than 16,000 people in 105 countries, some of which he shares during our conversation, he identifies these four core regrets that most people have. And these four regrets, Dan argues, operate as a kind of a photographic negative of the good life. And in it, and through our conversation today, we find out how regret, our most misunderstood, our most misunderstood emotion can be the pathway to our best life. So excited to share this best of conversation with you. I’m Jonathan Fields and this is Good Life Project.. Dan Pink is good to be hanging out again. Um, as after we have been jamming on and off in different ways on the mic behind the mic for many years now.
Dan Pink: [00:02:33] A couple of decades I think.
Jonathan Fields: [00:02:34] Now I think so, I think so, yeah. Um, we’re having this conversation in a really interesting moment in time and for so many different reasons. Um, 21 plus, 20 plus years ago, you write a book called Free Agent Nation, which basically predicts, um, a future where people are going to be en masse, um, exiting mainstream corporate culture to do their own things, hanging out their own shingle. Single. Solopreneur. Entrepreneur, freelancer. All sorts of different formats. And we’re sitting here having this conversation right now. And, um, you are looking like somebody who has this wise oracle who knew exactly what was coming.
Dan Pink: [00:03:11] Yes. That’s how I consider myself the wise oracle of Northwest Washington, DC.
Jonathan Fields: [00:03:17] So my recollection is when that book first came out, half the people were like, yeah, this is genius. And then there were a whole bunch of people who are like, this is insanity. No way. This is not the future. And here we are.
Dan Pink: [00:03:26] Yeah, yeah, yeah. So, um, yeah, that’s, you know, you know, as a writer and you know this too, um, what you want, you’re always. You always want a reaction. Um, the the only thing worse than people telling you you’re an idiot is people not saying anything. And and in that book. Yeah, it was a it was, it was divided. People said, oh, my God, you’re totally right. Um, and other people saying, what the hell are you talking about? But this is the case again, going back to my, you know, as a longtime Washingtonian, this is what’s known as in politics as being ahead of the voters. I think it was a little ahead of the voters on this one, but a lot of that stuff ended up being, you know, a lot of it ended up being more right than wrong. I missed a bunch of things, but it ended up being more right than wrong.
Jonathan Fields: [00:04:10] Yeah. I mean, it’s kind of when you look at the state of things today, given how much flux there is and how much change there is. I mean, you couldn’t have predicted the circumstance of the last two and a half years, but.
Dan Pink: [00:04:20] Oh, no, no, no.
Jonathan Fields: [00:04:21] But but even without that, like the trend was definitely on point. And we’ve seen so much exodus and so much flux and so much, you know. And now we’re sitting here and the phrase that’s been repeated mercilessly over the last three and a half months has been the, quote, great resignation. And then everyone’s seems to be throwing money at a problem, which I think is just rooted in something very different. You know, you can’t throw money at a meaning problem and expect things to be fixed. And my sense is that that’s really at the root of what’s going on. Curious what your take is.
Dan Pink: [00:04:54] On the great resignation. I mean, I think the great resignation is mixed. If you look at the like, part of me looks at the data and says that some of the great resignation are people who are a little bit older, saying, the hell with that, I don’t want to work anymore. Right? And part of it is people at the lower end of the labor market saying, wow, this job I had is really awful and I’m not going to take it anymore, which I think is a which I think is a, which I think is a good thing. And I think part of it is other people saying, you know, what’s the point? I don’t have any security. I’m not sure the system is actually configured that fairly. And here I am, two years into a pandemic reckoning with a sense of meaning and loss and what my life is about. Why would I want to stick around dealing with the nonsense at the Acme Widget Corporation, even if they’re letting me work remotely? But I actually am fairly, believe it or not, I’m actually fairly optimistic about this. And I’ll tell you why. This is, you know, in that book that you nobody but you and my wife seem to remember in that book, I did talk about remote work and basically saying that this divide between working one place and living another place is a historical aberration. It makes no sense in some ways, and that there’s a natural affinity between the two. And the only the big barrier is technology.
Dan Pink: [00:06:09] And even that people said I was some people said I was nuts about they said, you can’t trust people to work at home. You can’t. You know, it’s like if you have people working at home, we don’t have the technology to do it and you can’t trust them. They’re going to shirk. They’re going to play around working at home as an excuse for, for for slackers. And, you know, in March of 2020, we did this kind of insane international experiment where 100 million people around plus around the world did it in four days, and it was fine. And what I think is that that becomes a very hard egg to unscramble. And that the degree of autonomy that that you see in a free agent workforce and the degree of autonomy, the degree of autonomy that I think people need to live a healthy, meaningful life is, I think, deepening. And I think that’s generally a good thing. And so I do think that when we come out on the other side of that, this whenever that may be, that we’re going to come out of it, I think, with a somewhat reconfigured view of, of work, that people should have some amount of self-direction, that people should have greater dignity and control over their work, and that it’s actually intolerable in a society like ours to have jobs that are just horrible. And I really do think that the we’re going to head in that direction.
Jonathan Fields: [00:07:25] Yeah. I completely agree with you. I think, you know, the re-examining of the bargain we made that got us here is a really good thing. Yeah. And I think, you know, the choices that people are making. Now, on the one hand, I’m super excited about because I think people are making more choices in the name of purpose and possibility, on the other hand. I wonder if the metrics by which they’re making those choices are fully formed at this particular moment in time.
Dan Pink: [00:07:50] What do you mean?
Jonathan Fields: [00:07:51] Meaning that I, you know, like I have. And this kind of leads into, like, the topic of regret. I have a really big question mark over whether a significant percentage of the people who are opting into the Great Resignation are going to find themselves two years later in the great regret, because they they’re going to be in a different office, different paint on the wall, different boss, different industry, different job, different company. And realizing that here, here am I in this like all new place. And I did this and I kind of blew up a lot of things because it was normalized and it felt like it was more okay to do it in a way that I hadn’t felt before. And I went through the disruption of the change, and I’m not feeling any different than I did before. Um, so I’m curious. I’m really curious what the longer what the 2 to 5 year horizon is on when people reflect back, how is this all going to land?
Dan Pink: [00:08:45] I’ve given up on 2 or 5 year horizons because if we had gone back in time, think about having Jonathan thinking about having this conversation five years ago. Yeah. The world that has unfolded in the last five years is like something out of a bad comic, dystopian novel. And if I told you all the stuff that was going to go down, you would say, oh, come on. That’s like a bad screenplay. And we’ve been living through a bad screenplay. So it is five years from now. Who knows? Um, that said. That said, I do think that there that that that there is a reversion to the mean in general over time and everything. And so maybe we have a period coming up of relative calmness and normality. Maybe. Who knows?
Jonathan Fields: [00:09:32] Yeah. I mean, I do feel like there’s a window and it will at some point close. There’s a there’s a normalization of taking big, bold action that is not going to be perpetually open. So it’ll be interesting to see how it shakes out. Um, all right. So free Agent Nation to sell is human. Uh, drive when you have spent a lot of time writing about the human condition to sell as human, tell me if I got this right. If I remember this correctly, was the first book where you decided it was time to actually start to be the writer who wasn’t synthesizing other people’s work, and then overlaying my own input, but actually like bringing your own data into it. You start actually doing a lot of your own research.
Dan Pink: [00:10:10] Yeah. And that one I did. Absolutely.
Jonathan Fields: [00:10:11] Yeah. Which has been something that’s continued to this day. And it brings you in your, your newest to the topic of regret, which I was so curious about because I’m curious what led you to the topic. Clearly it’s super relevant in the moment, in time, in so many different ways that we’re in. But like you’re I know you’re working on this a long time before this moment. So why this.
Dan Pink: [00:10:31] Topic? Yeah, yeah, I started working in this pre-pandemic. And I think that the trigger, you know, again, I don’t really have epiphanies. Um, so I wish I did I have I have kind of slow hunches, but there was a, there was a moment on this one pre-pandemic. And. Yeah. And you might be able to relate to this because you and I are somewhat similarly situated and sort of where we are in life. But in 2019, my elder daughter graduated from college, and I’m sitting in this college graduation and it’s long. There’s like a lot of different things. And you know, her last name starts with P. So you got to wait a while. And so I’m thinking and I sort of have this, this weirdly distorted thought about how, wait a second. This kid was just born like this. She can’t be graduated from college. And then even worse than that, I’m thinking, wait a second, how can I have a kid who’s graduated from college? I graduated from college what is like four years ago, six years ago, you know, so I had that weird sort of time distortion. I started thinking about college and I’m like, God. And I started thinking about the regrets that I had in college. I started thinking, oh, God, you know what? I wasn’t I could have been a lot kinder. I could have worked harder. I could have taken more risks. And anyway, it just stuck with me. And I just happened to mention to a few people. And what was interesting about that is that people leaned in and when I say leaned in, I actually mean that in some ways physically, like I’m having a conversation with them, and they and they.
Dan Pink: [00:11:49] They want to talk more about it. They want to share their own experience. I’m like, wow, that’s interesting. That’s a very interesting reaction for a writer. And I was actually working on another project, and I started looking at some of the research on regret, and I was like, wait a second, this is super interesting. I think we’ve totally gotten this wrong. Me. And the other thing is that, you know, I was at a point in my life when this is something that I, that I actually wanted to contend with. I would not have written about regret when I was in my 30s. I didn’t have enough mileage on me. Now, in my 50s, I have some mileage on it, but I also have like a plenty of the road ahead and it’s like, yeah, I want to learn from what I did in the past and applied going forward. And so like so much of the stuff that I have worked on, like, you know, I only write books that I want to read myself, and this is something that I wanted to try to figure out and something that I wanted to learn from and figure out, like whether I was some oddball about the regrets that I had. Turns out I’m not and what I can do with them.
Jonathan Fields: [00:12:43] Yeah. And certainly you’re not the only person like you said as you when you bring up that term. People lean in. A chunk of years back we had Ronnie Ware on the podcast. Who was that? You know, the palliative care person who put on. I guess it was the early days of social media, like the five Regrets of the dying, and that went massively viral. That then leads to this book that goes massively viral. So there’s something about the topic that makes people say, huh, like, this is drawing me in. I want to know more. I want to understand this. And I wonder if it’s because the experience of regret is so universal.
Dan Pink: [00:13:18] Part of it, but also part of the answer to your question is in the title of your mammoth enterprise, your empire, good life. Mm. That’s the thing that surprised me here is that regret I was not I didn’t go looking for this, but I discovered in doing this research, particularly my my own research, not the research, I also I looked at a whole bunch of academic research on this. What I discovered, to my surprise, is that regret points the way to the good life. That regret teaches us about the good life in ways that almost no other topic does. That, to me, is that I think that’s at the heart of why people are leaning in. Now you figure that out. Good life is your free agent nation. People are. You know, you started this 20 years ago and you said, wait a second, people want to live a good life. And I think the phrase is brilliant because good means pleasurable, good means meaningful, good means moral, right. And so I think this is really at the heart of this, at least the research that I did on regret when I collected regrets all over the world. Those regrets, if you look at people’s regrets, the guts of people’s regrets and synthesize them, analyze them, they tell you what makes life worth living. Mm.
Jonathan Fields: [00:14:35] Yeah. There’s a lot of information embedded in them. Let’s do a little bit of defining when we use the word regret. What are we actually talking about?
Dan Pink: [00:14:42] It’s an emotion. Motion, and we’re talking about that horrible feeling that we have when we say, yeah, my things would be better right now, if only that’s the key phrase. If only I hadn’t done that stupid thing, failed to take that action, committed that that blunder. And it’s actually a remarkable thing that our brains can do. Because if you think about it, if I say I regret not being kinder in my, in my, in, let’s say, in college, all right. I regret not being kinder in college. So what I do, that very act is kind of amazing. What I do is I, I go back in time, I travel backward in time in my head, which is incredible in itself. All right. Then, I imagine what it would be like tell a story of the opposite of what really happened. Okay, so I’m telling stories. Then I get back in my time machine, I go forward in time and imagine how the present day would be reconfigured if I had done something differently. It’s. And we do it. So it’s incredible. So it’s a, it’s a, it’s a negative emotion where we feel crappy about something we did or didn’t do in the past. That’s what regret is, and it’s a terrible feeling. It’s a stomach churning feeling. It makes us feel bad. But here’s the thing. That’s the point. Because by making us feel bad, it helps us do better if we treat it right.
Jonathan Fields: [00:16:00] Yeah. I mean, I’m paying particular attention to the language that you use because it was you said it’s something that we did or didn’t do rather than something that happened, whether we had a role. Absolutely right and or not. Because I think of the concept of sliding doors, it’s like, ooh, if this thing had happened or if that thing had happened in my life would be profoundly different. But that’s it’s a different concept than when you have a sense of agency and control and power over that particular moment.
Dan Pink: [00:16:27] Agency is core to feeling regret. There’s a difference between regret and disappointment. Mm. Disappointment isn’t your fault. Regret, by definition, is your fault. I’ll give you one of the. They give you the best example that I that I’ve heard on this. It comes from Janet Lanman, who’s one of the early regret researchers at the University of Michigan. And she says, so imagine a scenario where there’s a little kid and she loses a tooth. And at night she, you know, she she takes her lost tooth. She puts it underneath her pillow as kids are want to do. And then she wakes up in the morning and the tooth is still there. Okay. She’s disappointed, but her parents regret not replacing the tooth with with a prize. All right. The parents had agency. The girl didn’t. I’ll give you another example. Okay, so this is. This is from. This is from my own life. All right. I don’t know how this happened. I’ve been trying to shake it my whole life. I’m a sports fan, and for whatever weird reason, I care. Okay, that’s a whole other psychological issue about why people care about sports. And I am a fan. As a long time Washingtonian, now a fan of the Washington sports teams, and I pay attention to the Washington Nationals and the Washington Wizards. All right. If the nationals, I give you the wizards that are more pathetic team. All right. If the Wizards lose, I’m disappointed, I really am. But I can’t feel regret. It’s not my fault. You know, I didn’t play. I didn’t pick the team. I didn’t coach. Right. And so there’s a big. So agency is important. And that’s partly why it hurts so much because in other circumstances we can look around and try to point the blame. Oh my God. What are you doing? Um, uh, benching, uh, Bradley Beal for half the game. Uh, what are you doing? Not playing close or defense on the Sixers, but in regret. I have no other person to blame. It’s my own fault. And that’s why it hurts so much.
Jonathan Fields: [00:18:16] And we’ll be right back after a word from our sponsors. So in order to experience regret, then you need to believe, even if it’s actually not a true belief, that you had in some way, shape or form, some control or some ability to control an outcome or an experience or a moment.
Dan Pink: [00:18:37] Bingo. That’s exactly right. And you’re on a very interesting point now. And I and I write about this toward the, toward the end of the book. Uh, and it’s and it’s this. So I did a part of the research for this. I did two large pieces of research for this. One of them was a quantitative survey. One was a qualitative survey. The quantitative survey took a sample of 4489 Americans and asked them a bunch of questions about emotions and whatnot, including regret. One of the questions I asked people was, do you generally think that you have some control over your life? Basically, a question about free will and huge majorities or huge majorities of people said, yes, absolutely. All right. Then I asked people, do you think that everything and most things in life happen for a reason, right. Basically the opposite question. And huge majorities of people said everything in life happens for for a reason. That is what we had was is that what we had is that people said, you know what? I believe that in fate and circumstance and I believe in free will, those two things go together and at some level leading a good life. Going back to the phrase that pays is depends on our ability to to to sort those out, to recognize. And I think regret teaches us this. To regret teaches us that our lives are a story in which we are both the actor and the author. We’re not the or the actor. Sometimes we’re the author other times, and understanding that is really important for our our well-being.
Jonathan Fields: [00:20:02] Mhm. So then if you don’t, if you buy into more of an an external determination ideal rather than self-determination, does that in your experience from what you’ve seen. Does that actually allow you to opt out of a certain amount of regret?
Dan Pink: [00:20:22] Um, I think it does. But the number of people who believe firmly in that more kind of purely fatalistic view, at least according to my numbers, is very small, is very small. The number of people who believe that fate, circumstance and things happening for a reason have nothing to do with their life is also relatively small. What I found is that most people believe in both and at first as a hyper rational guy, that really irritated me.
Jonathan Fields: [00:20:53] I’m saying things that happen, right? Right.
Dan Pink: [00:20:55] But but then. But then I realized that that’s actually my view was actually not very sophisticated, that this view that our lives are a mix of self-determination and circumstance, of things we can control and things that we can’t control is exactly right, and that our ability to tease those out is what leads to our sense of well-being and regret, teaches us how to regret, teaches us how to do that. But if you don’t believe in any notion of free will, or I don’t even say free will, it’s too far out of account. If you don’t believe you have any ability to determine the fate of your life, then you’re not going to have any regrets. And maybe in some ways you have exonerated yourself from that. But the number of people who actually hold that belief is quite small.
Jonathan Fields: [00:21:41] Yeah. I mean, because I’m thinking of, like, folks who opt into some sort of very rule based dogma or tradition, and that happens to exist in theology, in religion, in all these different cultural sort of like rules. If it is so rigid where you’re like, okay, I wake up every day and have the comfort of knowing that for almost anything that comes my way, there’s a rule that’s going to tell me how to behave. What is the moral behavior here? What’s the appropriate response? And you follow those rules and then something goes wrong. Like does that actually allow you to opt out of a certain amount of. Well, you know, I did what I was supposed to do and it didn’t end the way that I wanted it to end, but that’s not on me.
Dan Pink: [00:22:22] Yeah, there is and there’s and there is a kind of, you know, from Voltaire, I’ll, you know, Pangloss, who said, you know, when bad things happen, all for the best and the best of all possible worlds there is that that sort of delusional sense. But but what I found is that is that people. Once I said is that is that there aren’t a lot of people who believe that singularly, most of us have a more sophisticated, at least from my reading of my data. Most people have a more sophisticated, nuanced view of their of their lives as a mix of fate and circumstance, as a combination of things they can control and things that they can control. I think what’s important there is to know what we can control and and regret, I think, gives us some. It gives us a window into that. Yeah. What’s more like, as I’ve said, you know, I’d say in the book, the very existence of regret, the fact that it is so prevalent, it’s our most prevalent negative emotion. It’s one of our most common emotions of any kind. It is ubiquitous that everybody has regrets. The only people without regrets are people whose brains, like five year olds whose brains haven’t matured, and people with Huntington’s and Parkinson’s and schizophrenia and brain lesions, people who have some kind of disorder. And so the fact that it exists suggests that it has to serve some function, just like anything else in evolution.
Dan Pink: [00:23:41] And and I’m convinced that it serves an urgent function that the I think the evidence is overwhelming that it that a reason it’s one of our most common emotions is that if we treat it right, it’s one of our most useful emotions. What’s happened, though, is that in this country especially, we have gone a little bonkers on positivity. And so anytime we have a negative, we think, oh, negative emotions banish them. Terrible terrible thing. Positive. Sunny sunny sunny and the my one of my big points is that negative we should have positive emotions are great. They make life worth living. But if you have a portfolio with only positive emotions, it’s not going to work out very well for you. You need negative emotions to survive and thrive and pursue. Here comes the phrase again that good life that you have to have negative emotions in order to understand what makes things positive. And when we, when we, when we look at the hierarchy of negative emotions, the most important and valuable one is, is regret. And if we learn how to reckon with it systematically, we can. It has a whole array of benefits. It helps that improve our decision making and increase our performance at school. It can help our careers. It deepens our sense of meaning. It brings us closer to other people.
Jonathan Fields: [00:24:52] Yeah. I mean, it is fascinating how it’s been. We’ve always framed regret as something that is to be avoided at all costs. Yeah. Along with, like, everything that makes us feel bad, every emotion that sort of is on the negative side of the spectrum. And yet the research is pretty clear now, like a diverse range of emotion, diversity is what actually leads to a life that feels best. Not just this polytheistic look at like exactly all the time.
Dan Pink: [00:25:16] Exactly. Exactly, exactly, exactly. And I feel like this country gets it a little bit off that, that we’ve been seduced into a kind of a cult of uniformly positive thinking. And again, positive emotions are really, really important. We need to have plenty of them. You need positive emotions in order to lead a good life. But again. But only positive emotions is actually dangerous because you’re missing. You’re missing things. You’re not learning. You’re not growing. You’re not advancing. You’re not making progress. Mhm.
Jonathan Fields: [00:25:48] So we take sort of like the traditional view of regret as this is negative. It’s to be avoided. And rather than you saying well I feel differently, I’m raising my hand saying no. Like there are these there’s this and this and this. There are all these reasons that actually it’s positive. You go out and actually run your own studies. Um, two different studies. The American Regret Project, where you talked about the quantitative side of it, and then the World Regret survey, something like 16,000 people and over 100 countries now sharing their regrets, which alone is kind of an astonishing thing to just be able to sit with. I mean, when you start to see those coming in and you’re reading what people from all over the world are sharing, what’s happening in your mind.
Dan Pink: [00:26:30] I am astonished. I couldn’t believe how many I had. I had gone almost. I stopped. I had almost I didn’t almost no publicity, no spreading of the word. And all of a sudden I have all these things and I’m like, Holy smokes. Like, I don’t want to even. I’m not even going to talk about this anymore because it’s going to be too overwhelming. I mean, reading through 16,000 regrets takes a freaking long time. And, you know, I didn’t want to. And, you know, I and I think one of the things that I think it told me a few things. Number one, people want to talk about this. And there’s something about disclosure itself. And, and there’s subsequently some evidence of this, that something about disclosure of itself that helps us reckon with the regrets that holding them to tightly suppressing them is actually really bad for us. Um, second is that there is a universality in these regrets that really astonished me. And in this case, doing my own research was very helpful because I felt like the existing research didn’t quite get it right on what we regretted the traditional research on regret, on sort of what we regretted looks at the domains of life. It’s an education regret. It’s a career regret. It’s a romance regret. And what I found when you read through these things, one after another, after another after another, is this that there’s something else going on there? Let me give you an example of that.
Dan Pink: [00:27:46] So, um, if I the best example I think is this if okay, I got people who, let’s say people who went to college, let’s go back to we’ve been talking about college, let’s go back to and both of us have kids in college. So college is a friend of mine. So I think about I could literally I’m not joking around. I think that one could start a travel agency or a travel business geared toward people who went to college and now who graduated from college and now regret not studying abroad. The number of people like, okay, so so that’s like, oh, I wish I had like had hadn’t played it so safe and had studied abroad huge numbers of people like that. Okay, that’s an education regret. Meanwhile, I have hundreds of regrets around the world, literally around the world that have that essentially have the same format, which goes like this X years ago, I met a man, woman slash woman whom I really liked, and I wanted to ask him her out, but I didn’t, and I still regret it. That’s a romance. Regret. Then I have people going back to Free Agent Nation. All right. Oh, man. I always wanted to start my own business, but I never had the guts to do it. And now I’m in this lackluster job, and I really regret not taking it.
Dan Pink: [00:28:50] Okay, so that’s a career regret. Now, the traditional categorization would be like, oh, these are three different regrets to me. They’re the same regret. It’s a regret about taking a chance. It’s a regret about being bold. And what I found is that around the world, all these regrets seem to come back to the same four things. And there are four core regrets. And the universality of them is astonishing. The universality of regrets is kind of amazing. I mean, in a way, the quantitative portion of the survey was slightly disappointing on this front, because the reason I created a representative sample was so I could do cross tabs to say, oh, you know, um, uh, white people regret this and black people regret that. And, you know, um, women regret this and men regret that, and old people regret this, and, and young people regret that. And people in the eastern part of the United States regret this. And people in the western part of the United States regret that. And in fact, there’s not a huge amount of difference in white in that. So, um, you know, so, so, you know, so I did all this quantitative research, you know, you know, commissioning this, this expensive and really kind of awesome survey, only to find that there’s wasn’t a huge amount of difference based on things like gender and race and, and location. Um.
Jonathan Fields: [00:30:05] So it’s really just such a universal, um, experience, almost no matter where you are, no matter who you are. So your research shows that the old notion of domain based or role based regrets is maybe not really accurate. And you identify these four different categories.
Dan Pink: [00:30:23] I think it’s accurate. I don’t think it’s the big story. Okay. And I did that, I did I did my quantitative survey. I actually asked people to group it in domains. And what I found was something. What I found is that people regret spread across a whole number of different areas. It’s when I got to those when I, when I went to those 16,000 qualitative regrets and started looking through them and I said, okay, there’s something bigger going on here. And, and I think that that is the, the I think it’s useful to see what the domains of life in which people have regrets. I think that’s I think that’s super interesting. I think it’s more revealing to know that around the world, whatever the domain of life, these four core regrets keep coming up. Mhm.
Jonathan Fields: [00:31:06] So you mentioned one of them a boldness regret. Yeah. First I want to know a little bit more about that. And then let’s walk through all four of them because I think it’s really fascinating. So the boldness you say is is basically built around looking back and saying like I should have or like I didn’t do this thing.
Dan Pink: [00:31:22] If only I’d taken the chance, right? If only I’d taken that chance. All of these regrets begin at a juncture. You can go this way. You can go. That way you can play it safe or take a chance. And overwhelmingly, far fewer people regret taking a chance than playing it safe. Overwhelmingly, even if. Even if things don’t work out, there’s something. And I think that tells us something about about what a good life is. A good life is a life where we know that it’s not. We’re not here permanently. We want to do something. We want to learn. We want to grow. We want to test the limits. We want to do something psychologically rich. And I think that’s a fundamental human need. The there’s a fundamental human need for for growth. And the way we experience growth is that we we try stuff, we do something bold. And when we don’t, we regret it. So that’s one of the the four core regrets.
Jonathan Fields: [00:32:08] Yeah. Which is interesting that you focus on growth, not on having succeeded at the thing. Because, you know, when I think about a boldness regret, you know, part of it is the assumption that had I taken this action, it would have ended up the way that I wanted it to end up, which would be in some way what I assume is better than, you know, like the situation that I have currently, which may or may not be true, but what you’re saying is, regardless of that, like the deeper thing here is just having said yes to something where I actually I stand in place of agency, I take an action and there’s an opportunity for growth no matter how it ends up. There’s something about that, regardless of the outcome.
Dan Pink: [00:32:50] Absolutely. Because, you know, and you’ve done something. And I think that people it’s a great point, Jonathan. I think that people are pretty clear right about that. They even say, let’s take the regret about not asking somebody out on a date in those regrets, in the written, you know, in the in, the people say, oh, yeah, there was this guy Joe, and I was sort of in love with him and, and I think he was into me, but I was too chicken to ask him out. And then they say, like, I don’t even know if Joe and I would have gone anywhere. But I want to know, like, I wish I had tried that kind of thing. And so I think people are surprisingly, at least I was surprised surprise clear eyed about that. It isn’t about this. Some of it is about the imagined success. But it’s not really about that. It’s about God. I just should have done something. It is about that idea. It’s interesting because it goes to the other part. It’s like, it’s this. It’s this idea. Like, I had agency that’s a privilege and I didn’t use it. What a fool. Mm.
Jonathan Fields: [00:33:41] It’s almost like way, like a sense of wasted agency. Like, I wish I was the type of person who did X because I had the opportunity to. And maybe somebody didn’t. Um, interestingly. Okay, so that’s boldness. Foundation regrets. Talk to me about this.
Dan Pink: [00:33:55] Foundation regrets. Ah, if only I’d done the work. And these span a lot of domains. So it’s people who say, ah, I wish I had saved more money. I wish I had taken care of my body and exercise more. Um, if only I hadn’t smoked. If only I’d worked harder in school. I might be, uh, have more skills, that kind of thing. It’s choices we’ve made where it. Because of our choice, our foundation is a little bit wobbly. And to me now there are some interesting things about that. One of them is that that’s one area where I don’t think people and I mentioned this don’t have full 100% agency, because if you didn’t like work hard in school or you dropped out of college, is that only on you, or is it because you went to a crappy secondary school, or because you were weighed down with student loans or something like that? So. So that’s one area where people don’t have full, full agency. But to me, what it suggests is that a good life has some stability to it. That that and I use that word foundation intentionally. Like if your foundation is mushy or wobbly, that is not a good life. You need some degree of solidity as a base for that, for that life. And when people take action that erodes that, they really, really deeply regret it. Again, things like around the world, things like smoking, which would traditionally call a health, a health regret, but also, um, you know, financial regrets largely about, you know, spending over saving really was what it was. You know, and again and I use the, you know, the, the Aesop fable of, uh, the, the ant and the grasshopper. It’s like people regret being the ant and wish they were the grasshopper.
Jonathan Fields: [00:35:33] Yeah. This is it’s interesting because I was thinking about this particular category, and, um, this is the category where in my mind I was I got really curious. I’m like, I wonder what the quantitative overlay of this is, because this, like, you know, when you see, well, not everybody starts on equal footing, not everyone equal playing together. So like this is the domain. This is the type of regret where I’m thinking to myself that it could show up really differently depending on circumstance.
Dan Pink: [00:36:01] I think that’s right. And a big part of regret goes to opportunity. And so one of the things that you see, the one racial difference that I saw in the quantitative data is if you look at the surface domains, is that African Americans had more education regrets than white Americans. And I think it was largely because of their opportunity. I think we can assume that is that African Americans are more likely to have that educational opportunity thwarted or have that not be available to them. And so opportunity is, at the core, opportunities at the core of regret. And I think foundation regrets are, you know, I mean, I say this explicitly, I say this explicitly in the book, that that’s one area where your circumstances play a role. But at the same point, there is still agency. Yeah. And so that’s one area where it’s a little bit where it’s a little bit murky.
Jonathan Fields: [00:36:49] Yeah. And we’ll be right back after a word from our sponsors. The moral regrets. Tell me about this greater juncture.
Dan Pink: [00:36:58] You can do the right thing or you can do the wrong thing. You do the wrong thing and you regret it. And the two biggest types of offenses that I detected were bullying. Amazing. The number of people who regret bullying kids in school. They’re in their 60s and 70s and they look back. It’s bullying. Uh, it’s marital infidelity is a big regret that people have. You know, at some level, when I was, you asked how I was, what it was like when I realized all these people were offering regrets. I was thinking, Holy moly, I’m doing like, an online confessional here. You know, I feel like a priest and people are coming to me and just people are confessing. Uh, more regrets are tricky, though. It’s a relatively small category. But there, you know, our notion of what is moral, we don’t have a full understanding of it. Most full consensus of most of us agree that harming other people, swindling other people is bad. But when it comes to other kinds of things, how much should respect authority? How much should we value the sacred? Uh, there are some divides. The thing about moral regrets is that it’s one of those areas where I think we do have a lot of agency. At least people say that they have a lot of agency on these things. The other thing about moral regrets is that I find them heartening. I find it actually heartening that people are bugged by things they unethical, immoral things they did ten years ago, 20 years ago, 30 years ago. It suggests that we want to be good and that the need that this these moral regrets are surfacing is our need to be good. And I find that in some ways affirming.
Jonathan Fields: [00:38:28] Yeah. Which goes back to what you were saying in the earlier part of our conversation about there being real value in acknowledging regret, and then sort of like diving into it, what’s it’s actually telling us, what’s the data beneath the emotion.
Dan Pink: [00:38:40] Right. Right. And it’s also, you know, and again, moral regrets give us like all these regrets give us guidance for the future. But if you reflect on this, if you say, wow, wait a second, I really mistreated someone. I feel awful about that. I think that then people have said in the interview, said explicitly, you know, and because of that, because I felt so bad about that, it’s like I actually make a more affirmative effort to treat people better, you know, later on. But but it’s amazing how long these, these stick with me. I just remember one woman who I interviewed who was relating the story of I had to do all these interviews on zoom and I and I, which is not which is, you know, suboptimal and I and I, I got these interviews because in the world regret survey the qualitative portion there was a field I said, you know, if you’re interested in being interviewed, please leave your email address. And again, to your earlier point. And we had something like 30% of people opted in to be interviewed. Wow. Which was like I know, I couldn’t believe it. And I was expecting it to be like six, 7%. And so I got so, so, you know, so I interviewed I was able to interview a lot of people. But there’s one woman who I’m remembering. Her first name is Kim, who told a story about bullying a kid who I think she was like 8 or 9 years old. And even in relating the story, she’s in her 50s, so it’s like 40 something years later to to to me via zoom. She’s tearing up because she feels so bad about what she did. And what she did was actually not even the most egregious form of bullying that people revealed. But but there is something I do think there’s something affirming to that. We want to be good. Yeah, good. And this is this is why, like, a good life involves goodness. It doesn’t involve only pleasure. It involves morality and goodness, fulfilling your obligations, treating people well, and anything else that is a part of one’s moral code.
Jonathan Fields: [00:40:24] Yeah, I am in the early days of social media, which was not all that long ago. Um, I got a direct message, so I would have been in my 40s. I got a direct message from a kid who I grew up with, who I want to say I was probably 8 or 9 years old where I got bullied by this person, and 40 years later, you know, like, you know, 35, 40 years later, I get a message from this person out of the blue apologizing. Wow. Because this had been weighing on this person. And, I mean, I’m long over this, you know, like, this is like, way, way, way am I bothered, you know? And but this, like, this moment had been weighing on that individual’s mind for decades of their lives. There was this moral regret that, like you said, it just never went away to the point where they literally felt like they needed to reach out to me in any way that they could. And this was the one way they found where I could be reached out to, um, to make amends. And it was it was this moment for me where I’m like, wow, this is like I actually my heart went out to this person because I was like, I’ve been I’ve been over this for a really long time.
Dan Pink: [00:41:33] How did you respond?
Jonathan Fields: [00:41:34] Um, I basically like, like, you know, like we were kids. I mean, we all do stupid things, you know, and we all do things with, with outcomes that were not intended. And of course, you know, like, we move on and everything’s good. Um, but it was a real moment for me to realize how long people carry things that in their minds are, you know, like, are really big. And yeah, they’re just constantly they’re like, they never quite leave them.
Dan Pink: [00:41:59] And, and I think what’s interesting about that is that what advice that does that guy give to his own kids if he has kids. Right. And I think that’s the other thing about our regrets is that they offer guidance for ourselves, but we can deploy them to instruct others. And that’s certainly something that’s really important when people get get older. Like there’s, you know, if you’re in your if you’re in your 80s, you can still apply. You still have, you know, some of your life ahead of you, obviously. And you can apply lessons going forward. But another thing that people do in that stage of life is take their regrets, extract lessons from them, and try to share them with the next generation.
Jonathan Fields: [00:42:36] Right. And if you didn’t feel regret, then you don’t have the the lesson to share. I’m not saying you want to actually, you know, go do something just so you can have a regret. So you can have a lesson and you can have a behavior.
Dan Pink: [00:42:47] This is the paradox. Regret makes us feel bad. That’s the point, right? Don’t. By making us feel bad, it helps us do better. That’s the point. And this is this goes back to earlier what we were talking about. It’s like it’s why. So therefore, avoiding negative emotions is like avoiding ways to do better.
Jonathan Fields: [00:43:10] Mm. All right. The fourth one. Connection. Regrets.
Dan Pink: [00:43:13] Connection regrets. This is the biggest category. These are relationships. And what’s interesting about this is that it doesn’t matter what the relationship is. Really. Um, it could be spouse or partner. It could be toward your parents, could be toward your extended family, siblings, friends. Oh my gosh. The number of regrets revolving around friendship were incredible to me. Friendship. One of the things that I learned from this is, is how deeply important friends are in people’s lives and how bad they feel when friendships come apart and they usually come apart in slow, non dramatic ways. And what happens is, is that people want to reach out, but they say, ah, I don’t know. It’s going to be really awkward if I reach out and they’re not going to care anyway. And of course we’re totally wrong on both of those fronts. When people reach out, it’s not awkward and people do appreciate it. And one of the interesting things you might appreciate this as a writer is that in writing this book? I’m interviewing people and I’m trying to tell their story. And because of the nature of what we’re talking about, they say, I’m going to do something about this and they change the fricking story on me.
Dan Pink: [00:44:20] So, you know, and so, um, you know, so I ended up thinking that I had this, this, this, like, hermetically sealed lockdown, really tight little narrative. And they say, guess what? And I get an email. Guess what I did yesterday? That thing that I regretted not doing for 40 years. I decided to do something about it. And I’m like, oh man, okay, we got to get back on the phone because I gotta write. I gotta like, you know, I gotta tell this full story. But, uh, connection regrets, uh, suggests that, you know, I don’t think it’s a surprise, but what gives our life meaning are other people. And when those relationships come apart, it hurts. And to me, the lesson for that, it’s actually important to me, I think, personally, is the lesson I’ve derived from, from this is always reach out. Like I’ve changed my view on that, from these, from these all these regrets. My my lesson is always reach out. If you are wondering whether you should reach out, reach out. The very act of wondering suggests that you should reach out. Always reach out 99 times out of 100, it’s going to be well received. Always, always reach out.
Jonathan Fields: [00:45:24] So you use the word awkward as sort of like the basis for why a lot of people shared with you that they didn’t do that. And this is a word that I’ve seen pop up in the younger generation, like hashtag awkward. It stops so many of us. There’s something about the feeling of awkwardness that is so powerful and that we experience as being so negative, that it literally stops us from a simple reach out from repairing. We won’t. We would prefer to endure years and maybe decades of regret, rather than five minutes of awkwardness while we stumble through the conversation. But it is that powerful that it stops us. I mean, that’s kind of mind boggling.
Dan Pink: [00:46:06] Yep. And awkwardness. At least my reading of the. Melissa Dahl has a good book on this that I encourage your listeners to take a look at where she looked at some of the research on, uh, and just some of the, the circumstances of people feeling awkward. But but my read of the research on on awkwardness is that it’s like a, um, you see those cartoons where there’s like a, there’s a mouse. And but because of the nature of where the light is coming from, the shadow on the wall, it makes it seem like this giant beast. That’s what. That’s what. We completely overstate our fears about awkwardness and to the point where, as you say, very, very well. I wish I had said something like this in the book. It’s like we’re willing to endure years of regret instead of moments of awkwardness, which is absurd. But that has to do with sometimes. One reason people have foundational regrets is something called temporal discounting, where we are so concerned about pain in the short term that we are willing to, um to avoid pain. In the short term, we actually create pain in the long term.
Jonathan Fields: [00:47:08] Yeah, we’re weird that way. Um, well, we’re weird a lot of ways, but that way in particular. So we’ve got these four regrets. We all experience them to some level. Like you said, the research shows some of them are much lesser than under nearly as long, and they don’t happen nearly as frequently. But we all have like, our own like, special sauce flavor. We have our own stew, um, of some variety of all four of them. How do we how do we look at these different moments, these different experiences, regrets that we have and understand an intelligent process to then say, how do I extract the value in these? And then what do I what do I do about this? Um, in order to, to actually take this and not just make it a negative experience at endurance in my life. Like, how do we turn it into value and then how do we turn value into behavior?
Dan Pink: [00:47:59] Great. Great way to put the question. So so They’re. The way I look at this is there’s a three step process, relatively straightforward. One of them is self-disclosure. It’s very important that we disclose that that we talk about it regrets that we disclose our regrets. And once again, it’s another awkwardness overstated. We fear that when we disclose vulnerabilities about ourselves, people will like us less. They like us more. Um, they actually relate to us. They feel a greater sense of empathy. They admire our courage. So self-disclosure is the first step, even writing about them privately. There’s some good research from, uh, James Pennebaker at Texas showing that even private writing can relieve the burden of regret. So get it out there. And one of the things that one of the things that is important is I think it’s pretty interesting is that with negative emotions, they’re sort of abstract in a way, and by putting them in words, we make them concrete. And that in some ways I’m using mixing metaphors here, sort of defanged them a little bit that we that it’s a sense making function. Whereas when we try to explain positive experiences, We shouldn’t try to explain and make sense of positive experiences. We should just enjoy them because when we have positive experience and try to explain them, we actually drain some of the positivity from it. So disclose them. Second. Second step. I was blown away by the research on self-compassion. We should show ourselves compassion about these regrets.
Dan Pink: [00:49:20] And self-compassion is a triangulation between two extremes. One is self-esteem not terrible, has some benefits, but also has some big, big downsides. It corrodes empathy. It reduces persistence. It can increase narcissism. The other side of that, and I was also just blown away by this is self-criticism. And I was amazed. There’s very little self evidence that self-criticism is effective. I mean it’s kind of a waste of time. I mean, it seems virtuous. I certainly think it’s virtuous. I become expert in it over 50 years, but it doesn’t have that much of an effect. What self-compassion does is kind of steers between the complacency of of of self-esteem and the contempt of self-criticism, and allows us basically treat ourselves with the same kindness we treat somebody else. Recognize that we that that our mistakes, our flaws, our setbacks are part of the human condition, that we’re not that unique in that regard. And and what it does is that it it relieves the burden of it. It sort of it reduces the weight of it. If we treat ourselves like we would treat somebody else. And one of things about self-criticism is anybody when you and I are talking, I happen to be wearing a t shirt from a race that I ran a few years ago. And so, you know, when I run, I swear at myself, I insult. I would never talk that way to anybody else. And it turns out it’s totally useless.
Dan Pink: [00:50:51] And so what we should do is we treat ourselves with kindness rather than contempt and recognize treat ourselves with self-compassion. The final step is, is self distancing. We are terrible at solving our own problems. And what you need to do is you need to distance yourself in time, in space, even with language. So some well-known research about talking to yourself in the third person is a better way to extract a lesson going forward. In time, ten years from now and looking back and saying, what do I want? What will I have wanted? What what do I want to have done ten years from now? Asking yourself, what would you tell your best friend to do in this circumstance? Taking your regret and imagining yourself like in a clean room. Examining it as like a doctor of regret and saying, okay, what is this telling me? And that three step process disclose self-compassion and and self distancing allows us to extract that lesson now. Getting the lesson doesn’t necessarily guarantee the behavior right. But it’s the it’s the it’s the necessary first step. And for me, I think the the best way to the best way to promote the behavior is to be pretty stingy about which regrets you focus on. Only focus on the important regrets. Don’t try to fix everything. Take one regret, extract a lesson from it, and begin with simple steps to get small wins to apply that lesson in the future.
Jonathan Fields: [00:52:10] Yeah, that makes a lot of sense. And those those three different things. You know, it’s interesting. So self-disclosure really interesting that simply even like journaling it, writing only for yourself yes can have an effect. That’s that’s really powerful because I think a lot of resistance for people to be like, I don’t want anyone else to know, you know, like, this is I feel I feel a sense of shame around it. But knowing that you can literally sit down and just like, write it out in detail for only for you to see. And that alone can have a powerful effect is very freeing.
Dan Pink: [00:52:39] It’s very you could write about it for 15 minutes a day, for three days. I can do it. And if you don’t even like writing, you can talk about it in a voice recorder. Yeah. What it is, is it’s partly the disclosure in some ways disclosing it to yourself, but it’s also the sense making function that language has. That language takes these blobby mental abstractions and turns them into something more concrete. And that in some ways reduces the negative power of these. Of these emotions, that sense making function of language is really important, and that’s what disclosure does. But the other thing again I’ll give you another example from this, I have I had for a few people who I write about in the book. Their regrets were pretty significant and they were like reflected pretty badly on them. And I gave because I’m not I’m not an investigative journalist. I’m not trying to like, get anybody. I’m like, okay, listen, like if I really want to talk to you, I love your story. You know, if you want to use me just to use your first name, if you want me to, you know, you know, use a different name or something like that.
Dan Pink: [00:53:38] You know, you have to be fact checked and everything, but I don’t have we don’t have to reveal it. I had only two people who I had one person. That’s it. One person didn’t want me to use his last name. The other person. We came up with a made up name for her. But I have people talking about bullying. Talking about infidelity. Talking about not saving money for themselves. Talking about mistreating other people. Talking about doing really stupid things. Totally fine. Using their first and last names. And I think that says something. I mean, I think that self-disclosure is a relief. And the thing is like having to truly like to give you, I don’t think, less of people for revealing this. I actually can totally empathize with them. And I and I admire the courage of doing that, I don’t think. And that’s the thing, it’s like we’re totally we’re our predictions about how people are going to react are totally wrong. But but if you’re skittish, that’s cool. 15 minutes a day of writing about it. 15 minutes a day of talking about it into a voice recorder.
Jonathan Fields: [00:54:36] Yeah, it’s so powerful. And the notion of self-compassion also I find really interesting. I’m somebody who’s had a long standing meditation practice, and, you know, it’s a daily practice and at least once a week and oftentimes more than that, I swap in what we call the meta meditation or lovingkindness meditation. Yeah. And it’s an interesting meditation from the standpoint of self-compassion, because you go through a series of variations, you repeat the same phrase over and over, but over time you change who it applies to, and the first wave is always you apply it to yourself, right? So you’re like, maybe, maybe safe may be healthy. May it be, uh, you know, like at peace. May I live with ease. And you repeat that a number of times, and then you move on to someone you love, and then you move on to somebody you don’t know very well. And then you move on to someone who’s done you wrong, and then you move on to all beings. And what’s interesting is like, you know, you would think that in a meditation like that, which is effectively also kind of a form of prayer, the way you look at it, it should be other focused, and yet it always starts with you, you know, because you’re offering that same lens of loving kindness and self-compassion to yourself. And that’s no matter every variation I’ve ever seen, no matter how the language changes, it always starts there. And yet so many of us feel uncomfortable starting there.
Dan Pink: [00:55:53] It’s a great. Great point. I mean, that’s a great point. In some ways we do it the wrong order that we, you know, we show compassion. You know, we show compassion to others who we don’t even know. We give to charity. We feel bad for people who’ve been devastated by things. We show compassion to friends of ours who have been, who’ve been sick. We show compassion to people who’ve made mistakes. All of us have had friends or relatives come to us and say, oh my God, I just did something really stupid. I really screwed up. And we don’t, you know, we offer them compassion, but we don’t do it to ourselves. And and I have to say, I was I didn’t know much about this research on self-compassion. A lot of it was pioneered by Kristin Neff at the University of Texas. And I found it incredibly powerful that it really changed my view of both. I was always skeptical of self-esteem, but I was a true believer in self-criticism, and I think neither one of those are that great. What it really is, is self-compassion. Treat yourself with the same kind of huge extent to somebody else and don’t at some level. Not to be too harsh, but you know, if I’ll give you an example, um, you know, I have some moral regrets. I don’t love talking about them, but I have some moral regrets in my in my previous life. And and. At some level, I’m such an idiot. I thought I was the only one, and now I got these, like, everybody has these more regrets, and I’m like, oh, okay. You know, I’m not that special. Like part of having, you know, part of doing things, doing the wrong thing is, is the human condition. And I don’t want to become complacent about that, but I don’t want to say I’m the only one in humanity who’s ever done the wrong thing, and therefore I should be excoriated by myself. No, you want to show the same compassion to yourself that you would go to those other, you know, that we more, maybe more easily go to these other outer circles.
Jonathan Fields: [00:57:43] Yeah. And I think that’s got to be so much of the power of the database that you put together of the study. Also, when you start to see the numbers and you start, said, there’s no way for you to look at that database and say, you know, like 16,000 people from 100 plus countries. We’ve all experienced the same thing. We’ve all had the same, you know, like foundational quote failures or regrets or missteps or decisions I would have done differently and moral ones and this and that. And all of a sudden you’re like, oh, so I’m actually not the freak here. I’m just like everybody else. Like this is actually normalized behavior. So if we’re all in this together, then maybe if I actually own this and do something about it and maybe then it’s not going to make me like, cast out. But maybe it’s the thing that allows me to stay in.
Dan Pink: [00:58:31] Amen, brother. I mean, that’s what self-compassion does. It normalizes is to use your word, and then by normalizing, it neutralizes.
Jonathan Fields: [00:58:38] Um, yeah. So powerful. Um, you know, a lot of when I’m looking at the book and looking at the work you’ve been doing for a chunk of years now, it’s a really it’s a really big reframe. You know, like the net effect here is, let’s say, like, let’s all own the fact that regret shows up in all of our lives. It is, as you’ve identified, such a powerful, powerful emotion. And rather than saying, how do we how do we live a life where we never have to experience it? And how do we pretend that whatever we have doesn’t exist? How do we actually tap it? You know, like, how do we not using your language, not minimize it, but optimize around it?
Dan Pink: [00:59:10] Yeah. Yeah. I mean, I think that’s I think that’s it because I mean, I’m, you know, I’m a true believer now obviously having done the work. But the but it is a powerful emotion and it’s an incredibly useful emotion. But it’s tricky. I mean, you can’t, you know, listen, I don’t want to go. I’m not I don’t want to go overboard here. Like like if you spend too much time wallowing in your regrets, you’re going to be miserable. I mean, you know, you have to. It’s basically like we I don’t I don’t feel like in our culture, we have been taught how to deal with negative feelings. And I think that really goes to the heart of it. Like, like at some level, I think that in, like we’ve been. Some of us have been taught feelings of any kind. Ignore them. They don’t make any difference. They don’t reveal anything. I think, on the other hand, your people who’ve gone the other way, it’s like, oh, feelings are the only truth. And so if you do the first one, you and you ignore your negative emotions, you’re going to be diluted. If you wallow in your negative emotions, bathe in them, luxuriate in them, you’re going to be miserable. But if you say negative emotions are instructions, negative emotions are like emails or telegrams from the universe telling us things that negative emotions are, is, is are things that we should think about, that we should confront and think about, then they are incredibly instructive. They are much more instructive than positive emotions, there’s no doubt about that. And once again, in the hierarchy of negative emotions, our old friend regret sits there at the top. It is the most instructive negative emotion we have, Mhm.
Jonathan Fields: [01:00:48] I’m thinking as you’re sharing that, that some kind of an interesting reference popped into my head. I’m thinking about, um, the Jewish tradition sitting shiva after somebody dies and there’s this structure around, uh, effectively feeling it fully and utterly feeling it, surrounding yourself where it’s disclosed. You’re sharing your feelings, you’re being fully supported by everyone around you. And there’s there’s a process built around it. And then saying, like, you don’t never feel that again. But now it’s sort of like then you move into the next stage and it’s interesting to sort of say, okay, so like regret, like, yeah. How do you sit shiva for regret, you know, what’s the process by which? And that’s so much of what you’ve actually laid out in this book. It’s not just fascinating research. It’s like here’s process, like here’s how to deal with this moving forward so that we can actually, as you keep sort of circling back to that phrase that we have both been pursuing in different ways for so many years. Live a good life.
Dan Pink: [01:01:45] Yeah. But I mean, listen, I don’t want to turn this into a into a Talmudic debate, but let me let me see your Shiva and raise you Yom Kippur, that in the Jewish faith, right in the Jewish faith, there is a day where, you know, it’s it’s it’s it’s steeped in religion in that and it uses words like sin and atonement, which are stronger words and not and and religiously drenched words, obviously. Uh, but it’s that, that Yom Kippur, the Day of Atonement, says, okay, we are going to we’re going to reckon with these things that we’ve done that are wrong. We are going to reflect on them. But remember, Yom Kippur lasts only a day. So it’s not like, you know, if Yom Kippur was a was six months, you’d be miserable, right? It’s like we’re going to we’re going to take this stab of negativity, reflect on it and use it as a path to go forward.
Jonathan Fields: [01:02:41] Mm. Yeah. And I would venture to guess that we’ll probably find similar structures across so many different traditions.
Dan Pink: [01:02:48] Yeah, yeah. I mean, I mean, certainly in the Catholic religion, the, the, the idea of confessionals and, and, and then the expiation for these kinds of things. Again, I’m, I’m a very secular, very secular view of this. I think that there are echoes of this and that there’s a and what I think is, is true in certain that there are there are echoes of this. So certainly in the Catholic confessional, there is a sense making function that comes by putting these feelings of that you’ve done something wrong into words, and the ritual of disclosure and expiation is itself, I think, a useful ritual in the Jewish tradition. You know, Yom Kippur, where you reflect on your on your sins and you actually harm yourself by not eating? Um, again, those are there are echoes of this. And I think what it suggests, and we see this, we see this in a lot of work on, on on religion and how certain religious practices conform with what we know about psychological well-being. Not all, but but many of them do. And we also know that. And the evidence is overwhelming that people who have some kind of religious faith are happier and live longer in general than people who don’t. And, you know, those of us who are much more secular might not like that. But I think the evidence there is is overwhelming. Because what? Because it gives us a sense of purpose. It allows us to take these negative emotions and do something with them. We’re part of a community. And so again, I mean, I’m not I’m not just saying this just to be funny or because it’s you, but I think all of it goes back to this pursuit that we have this innate need. We have to lead a good life in all of the dimensions of that word. Good.
Jonathan Fields: [01:04:35] Yeah. And when it comes down to it. Right. And this is what you write in speaks specifically about, you know, like so regret may be a retroactive or a retrospective emotion, but we can, by not ignoring it, but by actually stepping into it, by addressing it, by using the three tools you suggested. And there are others that you write about within the book as well. You know, we can understand what it’s telling us so that we can look to our future, and it can inform how we step into our future differently.
Dan Pink: [01:05:04] I’ll give you I’ll give you your second amen of the broadcast. Amen.
Jonathan Fields: [01:05:07] Yeah. It feels like a good place for us to come full circle as well. Um, I’ve asked this question of you before. Years have passed since then, so I’m going to circle back and ask it again. So in this container of Good Life Project., if I offer up the phrase to live a good life, what comes up?
Dan Pink: [01:05:23] Yeah. To lead a good life is to love and be loved. I’m absolutely convinced of that. I’m absolutely convinced that I think that again, like as I say in the Jewish tradition, all the rest is commentary.
Jonathan Fields: [01:05:34] Mhm. Thank you. Hey, before you leave, if you love this episode, safe bet, you’ll also love the earlier conversation that we had with Dan about the powerful role of timing in life. You’ll find a link to Dan’s earlier episode in the show notes. This episode of Good Life Project was produced by executive producers Lindsey Fox and me, Jonathan Fields. Editing help by, Alejandro Ramirez, and Troy Young. Kristoffer Carter crafted our theme music. And of course, if you haven’t already done so, please go ahead and follow Good Life Project in your favorite listening app or on YouTube too. If you found this conversation interesting or valuable and inspiring. Chances are you did because you’re still listening here. Do me a personal favor. A seven second favor. Share it with just one person. I mean, if you want to share it with more, that’s awesome too. But just one person, even then, invite them to talk with you about what you’ve both discovered to reconnect and explore ideas that really matter. Because that’s how we all come alive together. Until next time, I’m Jonathan Fields signing off for Good Life Project.