Bestselling Author Daniel Pink Says Having Regrets Is a Good Thing

ELISE HU: That is bestselling author Daniel Pink. In his latest book, The Power of Regret: How Looking Backward Moves Us Forward , he explains how examining our regrets can help leaders learn and grow and gain better perspective. He even believes that we could all benefit from drafting a failure resume the same way we assemble a list of our achievements. We’ll be asking him how examining our regrets with the proper perspective can help us come up with the most useful New Year’s resolutions as we gear up for 2023. Dan is also a leading thinker on the future of where and how and why we work. So we’ll definitely get some of the latest insights on that topic as well. Here’s my conversation with Dan.

ELISE HU: Dan Pink, welcome.

DANIEL PINK: Elise, great to be with you.

ELISE HU: What drew you to the subject of regret in the first place?

DANIEL PINK: Well, I mean, I think it’s because I have regrets, like most people. I was at a point in my life where I had room to look backward. And when I look backward, there were things that I wish I had done, there were things that I wish I hadn’t done, there were things I’d wish I had done differently—and I wanted to make sense of that. That took me into this body of research on regret and also into some studies of my own. And the punchline of all of it is that, whoa, we’ve gotten this emotion wrong. We think that this emotion is inherently bad, that it always brings us down, that we should be positive all the time and never be negative, that we should look forward, not back. And that’s just terrible advice.

ELISE HU: Yeah. I mean, we, especially in America, I think, are socialized to be relentlessly good, right? When people ask you how you’re doing, you’re supposed to say you’re doing great.

DANIEL PINK: I’m great.

ELISE HU: Always, right? And then also, we’re in this kind of “no regrets” society and age. You write about how there are songs about this, this is a catchphrase that people kind of get tattooed on their bodies. Why is that counterproductive? What is wrong with thinking, hey, I should live without regrets?

DANIEL PINK: It doesn’t lead to learning growth or happiness. Otherwise, it’s a brilliant idea. But I think you make a really great point, Elise, about the Americanness of this. And I think the reason why people have fallen prey to this notion that they shouldn’t have regrets is that we Americans, as is our wont, have taken a good thing too far. We’re way over-indexed on positivity. And what we know about positive emotions is this: You should have a lot of positive emotions. Positive emotions make the world go around. I love positive emotions—gratitude, joy, elation, and so forth. But we shouldn’t have only positive emotions because negative emotions are helpful. They’re instructive. Fear is a negative emotion. It helps us get out of a burning building. Grief is a negative emotion. It helps us understand who we love and that we are loved. And one of the things that you see in literally 60 years of science is that when you take all of these negative emotions, when you line them up next to each other, the one that is most prevalent, and the one that I actually believe is most instructive, is regret. And so by ignoring our regrets—by being relentlessly positive, by always looking forward, never looking backward—we are missing opportunities to learn, to grow, to contribute, and even to love.

ELISE HU: How does regret help us grow and reflect and then live with more purpose? And I think this applies, obviously to life, but also… you know, this show is specifically about leaders, right, and the workplace. And so I’d love for you to connect the dots there.

DANIEL PINK: Sure. Regret in and of itself is neither terribly good nor terribly bad. It’s how we treat our regrets. And we haven’t been taught how to do that effectively. And so some of us ignore our regrets. So, we pretend we don’t have any regrets. We go and get a no regrets tattoo. But, some of us wallow in our regrets, ruminate on our regrets. That’s a bad idea too. That leads to despair. What we should be doing is looking our regrets in the eye, using them as a signal, as information, as data, and then drawing lessons from them. And here’s what social psychologists tell us: You put people into a negotiation session, then you say, tell me about what you regret doing or not doing in that negotiation. You actually ask people to invite this negative emotion. In general, they do better in the next negotiation. Same thing is true with problem solving. Put people into a problem-solving situation. Ask them, What do you regret about doing or not doing in this problem-solving situation? You’re not saying “no regrets,” you’re saying “get some regrets.” They do better in the next one. And so we have evidence showing that regret can help us become better negotiators. Regret can help us become better problem solvers. Regret can help us avoid cognitive biases like confirmation bias, like escalation of commitment to a failing course of action, which are two big biases that haunt leaders. Regret can help us become better strategists. And so what we have at our disposal is an emotion that, if we treat it right, can be monumentally useful to us as contributors and as leaders.

ELISE HU: What are useful ways to maybe systemize or implement in the workplace a reflective way to treat regret?

DANIEL PINK: The simplest straightforward thing that you can do, three steps: You tell your team, “Let me tell you about a regret that I have. Let me tell you what I learned from it, and let me tell you what I’m going to do about it.” One of the things that leaders fear is that when we talk about our regrets, when we talk about our mistakes in general, when we reveal our vulnerabilities, we fear that people will think less of us. And we have some pretty good evidence that most of the time, people think more of us. They admire our courage. They admire our authenticity. They admire our vulnerability. The other thing is, you can’t just say, “Here’s my regret” and leave it there. You have to extract a lesson from it. And then you have to say, “And here’s how I’m going to use that lesson to move forward.” Then what I found in talking to leaders is that when they do this very simple thing—here’s my regret, here’s what I learned from it, here’s what I’m going to do about it—that ends up triggering this incredibly rich conversation in the workplace.

ELISE HU: How do you think that this kind of reflection and looking inward at our regrets can be jump-started? Because I think still… especially leaders at major corporations came up or were educated to not show weakness or socialized not to show weakness. How do we take this more reflective approach, knowing what you’ve learned about regret and the social science on it?

DANIEL PINK: Well, two things. One, I think you model it. There was a time not that long ago when talking about purpose in the workplace was seen as kind of weird and woo-woo, and now everybody’s talking about purpose. There was a time that sort of talking about vulnerability was seen as soft. And that is changing a little, and I think regret is following that same kind of trajectory. So what it takes is it takes a few courageous early adopters to start modeling this behavior. But the other thing that is actually really important—and I think it’s for leaders, because we think somebody who is a leader is almost by definition a high achiever—is a practice known as self-compassion. There’s 20 years of research on this concept pioneered by Kristin Neff at the University of Texas. And it’s really the first step in how we as individuals reckon with our regrets. One of the things that you see, especially among high achievers, is that when they make mistakes, when they screw up, the way they talk to themselves is brutal. If you were to hear my self-talk when I make a mistake, when I screw up, when I have a regret, you would think I was nuts. If I were to use the self-talk that I direct to myself on other people in a workplace, I would be fired. Here’s what the research on self-compassion tells us: don’t do that. But the reason you don’t do that is not a kinder, gentler reason, Elise, it’s because it’s not effective. There’s essentially no evidence that that kind of lacerating criticism, self-criticism, boosts performance. It really doesn’t. Now, when you make a mistake, when you have a regret, when you screw up, treat yourself with kindness rather than contempt. You don’t need to treat yourself better than anybody else, but you shouldn’t treat yourself worse than anybody else. And, what’s more is that you should recognize that mistakes and screw-ups and regrets are part of the human experience. And any mistake that you made is a moment in your life, not the full measure of your life. And when we do that, when we practice self-compassion—again, triangulating between the sugary self-esteem and the lacerating self-criticism—that opens the way for us to make sense of our regrets, to find lessons in them, and then to draw lessons and apply them to the rest of our lives.

ELISE HU: What is the link between regret and purpose? Because both are now in vogue these days.

DANIEL PINK: It’s an interesting question. So I did some research, and what I found is that around the world, people seem to have the same four consistent regrets. People have regrets about not doing the work of saving money or taking care of their health or learning, and that erodes the stability of their lives—those are foundation regrets. People have regrets about not taking chances—boldness regrets. People have regrets about not doing the right thing—moral regrets. People have regrets about not reaching out to people they care about—those are connection regrets. We know what people regret the most. We understand what they value the most. And if we understand what people value the most, we understand, why are we here as human beings doing what we’re doing, that we understand at some level the purpose of life. And so the connection between regret and purpose is this: when we’re trying to lead a purposeful life, we should be locked in on avoiding regrets about foundations and about boldness and about morality and about connection, and actually chill out on everything else.

ELISE HU: I love that. How did you study regret?

DANIEL PINK: Well, I did a few things. I looked at about 60 years of scientific research in social science, social psychology, developmental psychology, cognitive science, neuroscience. I did a very large public opinion survey, and then the most exciting thing, at least for me, was something called the World Regret Survey, where I set up a website, worldregretsurvey.com, invited people around the world to share their big regret, and we ended up with a database—it’s crazy—of 23,000 regrets from people in 109 countries.

ELISE HU: I would love to better understand, especially since you did that worldwide study on regret, what were people’s attitudes about work and regret? Did they generally regret working so much, or did they regret the choices they made in work?

DANIEL PINK: It’s a really interesting question. It’s both. I guess there were three broad types of work-related regrets. One of them was choosing a profession or a career course because someone else wanted it rather than they wanted it—leading someone else’s life, not being authentically themselves, not having the gumption to lead their own life. That was fairly common. There were some regrets, although fewer than I would have expected, of people who said, “I work too much, and as a consequence, sacrifice my family and people I love.” But the big workplace regret was not taking chances. You’re at a juncture in your life. You can take that job in a city you haven’t been to, or you can play it safe and keep working at the job in your hometown. You can speak up when you see something going wrong in your workplace, or you can just shut up and go along. You can leave your lackluster job and start a business, or you can stick around because it feels safer. And when people are at that juncture—play it safe or take the chance—most of the time, not all the time, but most of the time they regret playing it safe. And it comes out a lot in the workplace.

ELISE HU: Based on what you’ve learned about how people regret speaking up for themselves or taking risks, what’s the takeaway, how is that instructive, do you think?

DANIEL PINK: I think what it means is that, if we’re right, that people have regrets about not speaking up—and that is the kind of regret that doesn’t singularly fall on their shoulders—I think it’s up to leaders to provide environments where people feel free and safe to speak up, to dissent, to disagree with the boss, and also to take some risks to try stuff. And even if it doesn’t work out, they’re not going to get sacked, they’re not going to get excoriated if they do that. Now, a way to do that is this, if you’re a leader, is to not only tolerate dissent, but to welcome it, to invite it, to be at a meeting and say, “Who disagrees with me? I really want someone to disagree with me.” Or when someone disagrees with you, say, “Oh my God, I’m so glad you disagree. Thank you for disagreeing with me.” Really invite that. Create the conditions in which people feel emboldened to do that. Likewise with taking risks. Let’s say that you’re a boss and you’ve got a colleague named Fred, and Fred tries something and it doesn’t work that well. But it was a pretty intriguing idea. You say, “You know what, Fred had this idea, he tried it, it didn’t work. Let’s all give him a round of applause for being bold and trying something new.” Celebrate sensible risk taking, and you invite dissent. And when you do that, people are going to feel more emboldened. They’re going to feel psychologically safe. The lack of psychological safety thwarts productivity. It thwarts creativity. It thwarts a sense of belonging.

ELISE HU: I think applied to us as individual workers, though, too, that negative self-talk is something that, at least for me, really animates fear, and then it makes us less likely to take chances.

DANIEL PINK: Sure. Because what you’re doing is, like you just said, “Oh god, if I take a chance and it goes wrong, I’m going to beat up myself. Whereas if it were a colleague who took a chance and it didn’t go right, you wouldn’t say, “You idiot, what’s wrong with you? You don’t know what you’re doing.”

ELISE HU: I would not do that. You’re right.

DANIEL PINK: But you wouldn’t think that. Again, the lesson here is not some kind of Stuart Smalley, touchy-feely approach to things. The lesson here is, don’t treat yourself worse than anybody else. You should treat other people with kindness. You should treat yourself with kindness. And the reason to do that is not only is it easier, it’s more effective.

ELISE HU: Okay. Before we let you go, I’d love for you to talk through some practical ways that we can use regret to help us grow and develop. So how do we do it?

DANIEL PINK: Okay, all kinds of great things you can do here. One of them is an idea from Tina Seelig at Stanford University [and it] is to write a failure resume for yourself.

ELISE HU: Failure?

DANIEL PINK: A failure resume, yes, stick with me here. Everybody, especially leaders, have resumes, they’re these glorious compilations of all the great things that they’ve done. A failure resume is the inverse of that. And what you do is this: You list all of your failures, your setbacks, your screw-ups, your blunders. So, think about a spreadsheet. List all of those in one column. In the second column, though, you list, What lesson did I learn from it? And in the third column, you list, What am I going to do about it? Now, I’ve done a thorough inventory of all of my failures. It’s painful. Another exercise that I like—again, using the power of regret—it’s something known as a pre-mortem. A pre-mortem. It’s a way to avoid regrets. We know what a postmortem is. A postmortem is, you examine the body to figure out why the body died. A pre-mortem is when leaders do that with projects, in advance of a project. So, let’s say you’re about to launch some project. You gather your team and say, “Team, let’s all get in our mental time machines and go two years into the future and imagine that this project is an abject disaster. Let’s talk about what went wrong.” And people know this—oh, we didn’t have enough budget, we didn’t have the right people, we had too many people, we didn’t have buy-in from the top. And you list those things, and then you get back in your time machine, go to the present, and don’t do those things. A pre-mortem. It’s a fantastic planning technique to avoid regret in the future. Another way to steer yourself into greater boldness: recognizing that many leaders have regrets about boldness is a technique from the great Andy Grove, the former CEO of Intel. One of the things that he would do when he was faced with a tough decision is that he would ask himself, If I were replaced tomorrow, what would my successors do? What it usually meant was that he knew that the right thing to do was to act boldly. He knew the right thing to do was to take the high road. But that form of self-distancing—imagine if it was someone else who replaced him, helped him make the right decision for himself and for his team. So there are all these, I think, really cool, interesting techniques that leaders can use to begin to get a little bit better at harnessing regret for advantage and, you know, and find their footing in dealing with a negative emotion that they haven’t been taught how to deal with effectively.

ELISE HU: Yeah. I love all of these, even though it seems daunting to do an inventory of failures.

DANIEL PINK: It is daunting. I did it for myself and it was kind of exhausting. Believe me, I did not put my failure resume on LinkedIn. Maybe that’s a business idea we have—LinkedOut. You know, everybody lists their biggest mistakes. It’s actually not a bad idea, Elise, we should go into business.

ELISE HU: Yeah, I feel like it could really increase the amount of compassion that we have for one another.

DANIEL PINK: I think that’s a good point. And I think that when leaders do this, when leaders show fallibility, but not in a way where they’re beating themselves up over it, where they say, “I learned this from it.” Yeah, you elicit compassion. But I actually think you show compassion because when you behave in that way, you’re inviting other people to say, you’re allowed to be human in this workplace. Let’s all do our best together. Let’s all treat each other well. And when we do that, we can shed a lot of the baggage that I think slows people down in doing great things and contributing to the world.

ELISE HU: Speaking of being human, this is the time of year when a lot of us are thinking about New Year’s resolutions or coming up with a list of them. And I guess I could see New Year’s resolutions as a kind of pre-mortem for our years that we could put together. So how could regrets be a good resource for drawing those up for us?

DANIEL PINK: One of the things about New Year’s resolutions is, it’s not like going to the grocery store of life where you go in with a giant list. If you have a giant list of resolutions, you’re screwed. You know, you don’t want to walk down every aisle of your life taking stuff off the shelf. What you want to do is you want to focus on literally one or two, one or two New Year’s resolutions. Now, how do you do that? I think one way to do that is to use the end of the year to reflect on your regrets. So if you think about it this way: ask yourself, What is one thing that I wish I hadn’t done this year, and what does that teach me and what does that instruct me to do in the new year? Also, What is one thing that I wish I had done this year, and what does that teach me and what am I going to do with it this year? So let’s say that you say, I wish I hadn’t yelled at my team as much as I did. That’s a regret. Well, that’s telling you something. What it’s telling you is that you value kindness, you value respect. And in the new year, what you should do is that if you’re feeling that well of anger rise up in yourself, go take a walk before lashing out. That’s a very appropriate New Year’s resolution. Or if you have a regret about inaction, even if it’s a personal regret, say, ah, I had a chance to go travel to such and such a place and I didn’t do it, and now I regret it. I think you have to say, You know what? In this new year, when I have a chance to act, I’m going to have a bias for action. My default setting is going to be to act, and there has to be a strong reason not to act. So if we say, Should we try this small experiment at work? The answer is yes. You’ve got to give me a good reason not to do it. Should I take this trip? The answer is yes. You got to give me a good reason not to do it. Use your old year regrets to fashion your New Year’s resolutions. But seriously, guys, just take one or two New Year’s resolutions.

ELISE HU: Okay, Dan Pink, this isn’t explicitly about regret, but I know it’s an interest for this show and something that you have written about, which is the future of work—where we’re working, how we’re working. It’s all changed a lot in the past couple of years. We’re in a far more flexible model than a few years ago, so any predictions for how work will change going forward, knowing what we know?

DANIEL PINK: Well, I mean, I think that the next year is going to be really super interesting. One of the things that I think we’re realizing now is that, post-pandemic, or at least we hope post-pandemic, companies and organizations are sorting out some pretty fundamental questions about work. I don’t think we have answers to them, but I think together we’re going to sort them out. Questions like, What kind of work should be done together and what kind of work should be done solo? We’ve been making it up since there’s been white-collar work. Honestly. To me, I think that we’re a little bit over-indexed on collaborative work, and as a consequence of that are draining some of the value of collaborative work. What kind of work should be done asynchronously and what kind of work should be done synchronously. We’re so meeting-prone. I think we do a little too much synchronously and not enough asynchronously. Other important questions: What’s an office for today? Truly, what’s an office for? That question is big time up for grabs. So I think that we are in this kind of great sorting period where we’re going to sort these things out. Where it’s going to come down, I don’t know. But one thing that I think seems very clear in the data, we are essentially entering, in many forms of white-collar work, something akin to permanent hybrid. A year from now, I don’t even know if we’re going to call it hybrid. The analogy that I think about is, at about 4:30 each evening, my wife and I have the day’s most important conversation, which is, What are we going to have for dinner? So sometimes I will cook, sometimes she will cook. Sometimes we’ll have food delivered, sometimes we’ll go pick something up. It’s hybrid eating, right?

ELISE HU: You don’t call it hybrid eating, though.

DANIEL PINK: Exactly! We just call it having dinner . And so I think that’s where we’re going to go. And I think that’s a happy world—a world where workers have greater autonomy, where we’re more thoughtful about when we collaborate and when we do stuff solo, where offices are not rows and rows of soulless cubicles, but are more like cafes or nightclubs or lounges where people can come together. I’m pretty optimistic.

ELISE HU: And hopefully it’s a world where leaders are using their regrets in meaningful ways.

DANIEL PINK: Let’s hope. Let’s hope that leaders actually take the lead and recognize that, yeah, we should be positive most of the time. But negative emotions are part of life, and negative emotions are some of the most instructive tools in our toolbox.

ELISE HU: Daniel Pink is the author of The Power of Regret: How Looking Backward Moves Us Forward . Dan, it’s always such a delight to talk with you. Thank you.

DANIEL PINK: Thank you, Elise. Always a pleasure.

ELISE HU: Thank you again to bestselling author Daniel Pink for that conversation. Again, the name of his latest book is The Power of Regret: How Looking Backward Moves Us Forward . It was one of my favorite books of the year. And that’s it for this episode and this season of the WorkLab podcast from Microsoft. Thank you so much for listening. We explored so many topics in Season 3, from productivity paranoia to the human energy crisis. From what Gen Z wants out of work to what games can teach us about leadership. Thank you for coming back week after week, and we will be back again in a few months for Season 4. In the meantime, check out the WorkLab digital publication, where you’ll find transcripts of all our episodes along with thoughtful stories that explore the ways we work today. That’s at Microsoft.com/WorkLab. And as for this podcast, please rate us, review, and follow us wherever you listen. That always helps us out a lot. The WorkLab podcast is a place for experts to share their insights and opinions. As students of the future of work, Microsoft values inputs from a diverse set of voices. That said, the opinions and findings of our guests are their own, and they may not necessarily reflect Microsoft’s own research or positions. WorkLab is produced by Microsoft with Godfrey Dadich Partners and Reasonable Volume. I’m your host, Elise Hu, and my co-host is Tonya Mosley. Our correspondents are Mary Melton and Desmond Dickerson. Sharon Kallander and Matthew Duncan produced this podcast. Jessica Voelker is the WorkLab editor.