How looking at past mistakes with a different mindset can help us make better decisions.
“No regrets” might be a popular modern-day mantra, but it’s virtually impossible to live your life without wishing you could do certain things over. Some people try to ignore these feelings; others wallow in them. But author Dan Pink, who recently conducted large U.S. and global surveys on this phenomenon, says the right approach is to instead carefully consider what we regret and why so that we can either reverse course or make better decisions in the future, as well as putting them behind us. Whether you’re frustrated by bad career moves you’ve made, business ideas you didn’t pursue, or relationships you’ve let falter, these regrets can be useful tools for personal growth. Pink’s new book is The Power of Regret: How Looking Backward Moves Us Forward.
ALISON BEARD: Welcome to the HBR IdeaCast from Harvard Business Review. I’m Alison Beard.
PERSON 1: I wish I didn’t worry about what other people think.
PERSON 2: I regret pretending to be less smart than I actually am simply to please others.
PERSON 3: I regret following a career path for money instead of for my passion.
PERSON 4: I regret putting my life on display for so long on social media.
PERSON 5: I wish I tried harder to foster deeper relationships with my work colleagues.
PERSON 6: I regret ignoring my inner voice and not heeding its plea to be more adventurous, like moving country or changing job when the boss sucks.
PERSON 7: I regret not being kinder. I was too concerned with being right.
PERSON 8: I regret every big decision I’ve ever made.
ALISON BEARD: In case you hadn’t guessed, today’s episode is all about regrets. Why we have them the most common kinds and how to not only get past them, but maybe also harness them for good. Our guest is bestselling author, Dan Pink, and the quotes you just heard from a big study he did asking people all over the world to write in and tell him about their biggest regrets. His latest book, based on that research and the work of many others is called the “Power of Regret: How Looking Backward Moves Us Forward.” Dan, I’m so happy to dig into this with you today.
DAN PINK: Alison, I’m so glad to be with you.
ALISON BEARD: So, let’s start with the basics. What is regret and why do we humans feel it so very often?
DAN PINK: Two very important questions. So regret is an emotion. It’s a negative emotion and it’s a backward-looking emotion. So we feel bad when we look backward and say to ourselves, if only, that’s the catchphrase, if only I had decided differently, taken a different path, the present would be better. And so it involves this incredible ability of us to travel through time in our heads, to negate what really happened and re-imagine a present based on that negated past. It’s crazy. I mean, it’s incredibly cognitively sophisticated. Now it’s also ubiquitous. Everybody has regrets. It’s one of the most common emotions that we have. And you have to wonder why something that is so aversive that it hurts is also so common. And I think the answer to that is pretty clear. It’s because regret, when we treat it right, is useful, it can help us.
ALISON BEARD: I get evolutionarily why something like anxiety and negative emotion would be helpful because you’re thinking about the future and that’s helping you prepare for it. Why is regret also helpful when in most cases you can’t change the past?
DAN PINK: Because we can learn from the past. Because it provides guidance to us. And I think that it’s a really, really important question you’re asking there because we sometimes fall prey to the idea that we should never look backward, always gaze forward to the future, always be positive and looking backward is dangerous and that’s wrong. Looking backward is one way that we learn. It’s actually an incredibly important way that we learn. And when we process regret properly, it has two very powerful attributes. One is that it clarifies what matters to us. When a regret lingers that tells us something. If you make a mistake and a week later, you don’t care about it or you take an action. And a week later, two weeks later, a month later, you don’t care about it, that tells you something too.
But the regrets that linger with you are clarifying. They tell you what matter, what’s more, they instruct you how to do better in the future. The trouble is with regret like many negative emotions, we haven’t been taught how to deal with them properly. And so what happens is that we either ignore them, which is dangerous. It leads to delusion. We don’t learn or we get captured by them and that leads to despair. And what we need to do is be able to confront our negative emotions, particularly, this incredibly common or most common negative emotion of regret.
ALISON BEARD: So the research you did for this book was so interesting, surveying people all over the world. What did you find about the most common types of regrets that people have?
DAN PINK: Well, along with looking at the academic literature, I did two pieces of research of my own. One was something I called the American Regret Project, which was a large quantitative survey of the US population. And so I had asked people to give me their regrets and then they put them in categories like career and family and relationships and health. And I found that people regret a lot of stuff. It’s all over the place. So a very unsatisfying answer. Now the good news here is that I also did another piece of research, a qualitative piece of research called The World Regret Survey, where I simply just asked people around the world to tell me one of their regrets, tell me one of their biggest regrets. And to my surprise, with just a couple of tweets, we ended up with 15,000. We’re now over 18,000 regrets from over a hundred countries. It’s crazy.
ALISON BEARD: It’s like a little bit of a confessional, I guess.
DAN PINK: It was very much an online confessional. And when I read through those and I read the vast, vast, vast, vast, vast majority of them, I discovered something else that one layer down there was something else going on in people’s regrets that the domains of life didn’t so much matter. What really mattered was this underlying almost hidden architecture of motivation and meaning. And I found that around the world, people over and over again, it was really surprising to me. People ended up regretting the same four things
ALISON BEARD: And take us through them.
DAN PINK: So one of them is what I call a foundation regret. A really big one was not saving money, right? So, I spend too much and save too little. Others foundation regrets, outside of the United States, I had a huge number of people regretting smoking. These are regrets about the small things that we didn’t do typically, or did wrong early in our life that each one didn’t have a cataclysmic effect, but the accumulated effect of these was huge. So foundation regrets are, if only I’d done the work.
Second one, I think really important with regard to careers and business. These are boldness regrets. And some of the regrets that we heard at the top of this show were very quintessential boldness regrets. I have, among American college graduates an astonishing number of regrets of people who regretted not studying abroad when they were in college. Hmm. I mean, yeah. I was surprised by it. Did you study abroad in college?
ALISON BEARD: I didn’t. I traveled a little-
DAN PINK: Do you regret that,
ALISON BEARD: …but I didn’t.
DAN PINK: Yeah. Is that a regret for you?
ALISON BEARD: No, only because I ended up moving to London for five years when I was in my twenties.
DAN PINK: Of course. Okay.
ALISON BEARD: So I feel like I did it then.
DAN PINK: So you extinguished that. Well, a lot of people haven’t extinguished that, it was a surprisingly common regret among college graduates, Alison, to the point where, and this is where your listeners can step in. There’s a business idea here. There’s a travel agency to be started that serves American college graduates who didn’t study abroad and regret it, and now want to do something like that.
ALISON BEARD: And that’s another boldness regret. I didn’t start that business. I wanted, I didn’t pursue that brilliant idea that would made millions of dollars.
DAN PINK: That’s another boldness regret. I stayed in the lack luster job and didn’t start a business. Another one is not asking people out on a date. And so if you look at these regrets, one is an education regret. One is a career regret. One is a romance regret, but they’re all the same. It’s a regret that says if only I’d taken the chance and that’s a boldness regret.
So third category, moral regrets. If only I’d done the right thing, you’re at a juncture, you can do the right thing. You can do the wrong thing. You do the wrong thing. These were often regrets about bullying, marital infidelity, those kinds of things.
And then finally there are connection regrets, which are about relationships, but not necessarily romantic relationships. In fact, mostly not romantic relationships, relationships with parents and kids and siblings and relatives. And, oh my gosh, a lot about friends. Where a relationship was intact or should have been intact. It drifts apart, one side wants to reach out. They don’t reach out. They think the other side’s not going to care. They think it’s going to be awkward to reach out so they drift apart further. And then in certain circumstances, it’s too late. So connection regrets are if only I’d reached out. And over and over again, these are the regrets that kept coming up. And it didn’t really so much matter to the domain of life. What mattered was, what was going on underneath, beneath the surface.
ALISON BEARD: And there’s another theme that I saw in the book and I hear when you’re talking and that sort of action versus inaction, do people regret the bad things they do, or the mistakes they make more than the chances they didn’t take or vice versa.
DAN PINK: That is a hugely important issue. When we think about the architecture of regret, as exactly as you say, Alison, you can have a regrets of action. I regret what I did or regrets of inaction. I regret what I didn’t do.
In our twenties or so people have equal numbers of regrets of action and in action. But as they age, like even into their thirties, well into their forties, fifties, sixties, seventies, they have many more regrets about inaction than about action. And I think that’s because with an action regret, let’s say you’ve hurt somebody, yeah, you can apologize. You can make amends. There’s certain things that you can undo. You can make restitution. You can sometimes see if you can find a silver lining in them. But the inaction regrets really, really nag us.
ALISON BEARD: And I know you didn’t categorize things this way, but this is a Harvard Business Review show, so I do want to dig into sort of career and work related regrets. We heard that sampling in the intro. What else did you find there? What were some of the themes that came out?
DAN PINK: And, the career, yeah, it’s very interesting because even the career regrets seem to group into these categories. And I think that the biggest ones were boldness and connection regrets. Boldness is a very, very interesting category for career regrets because it wasn’t only people saying, “Oh, if only I had started a business.” There were a very large number of regrets about speaking up.
There were very few people who felt that they had excesses of assertiveness or even extroversion, but there were people who felt that they were hobbled by meekness, by not speaking up, by timidity, by what they called introversion.
And I really think that these speaking up regrets are a message to organizations that you want to provide places where people feel emboldened to speak up. Connection regrets were actually really interesting too. There’s one that really sticks with me. And it’s representative of a decent number of regrets. And it’s a guy who, he didn’t leave his email address. So I don’t know who he is. He’s a 60, all I know he is a 62 year old man from Pennsylvania.
ALISON BEARD: That was one of the quotes I chose. I wish I’d tried harder to foster relationships, but you can give the extra detail, which I cut out of the quote.
DAN PINK: Exactly. That was in there because, because it’s the other part that really stuck with me and really, and saddened me because he said, “I wish I had had fostered better connections with my work colleagues.” And he goes on to say, I’ve been working at the same place for 30 years and I don’t feel like anybody I work with is really a friend. I mean, that’s incredible.
ALISON BEARD: And sad.
DAN PINK: I found that one really sad. There’s a lot of sadness. There’s some sadness in these regrets. There’s actually, I think a lot of aspiration and joy and reaching for something better in life in there. It’s surprisingly, it’s weirdly uplifting to read all these regrets. I mean, I know that sounds strange, but that one, that one has really stuck with me. This man who’s been working at this place for 30 years and doesn’t feel like any of the people he’s worked with are his friends. And again, if I had talked to him, I’d say, you know what? That might not be entirely on you. It might be something about the culture of the place where you’re working.
ALISON BEARD: Okay. So I want to get into sort of either getting over regret or harnessing regret for good. My first question is about the former, we don’t want people getting stuck in rumination and sort of rethinking every decision they’ve ever made. What’s your advice for people on how to not get stuck in that way, particularly when it’s a mistake that can’t be changed?
DAN PINK: The starting point is for all regrets in my view is how we treat ourselves. And one of the things that comes out very clearly is that the way we talk about ourselves is ridiculous. It’s cruel it. We talk about ourselves with such savagery. We would never treat anybody else that way. I mean, if you heard the way that I talked to myself when I exercise, you would think I was a madman. Like I shouldn’t be around other people. And there’s very little evidence that’s effective. That’s the thing. That’s crazy.
What’s more effective, and we have 20 years of research on this, is something called self-compassion. Treat yourself with kindness rather than contempt. Treat yourself with the same kindness you treat, somebody else recognize that your mistakes are part of the human condition. Look at your mistakes as a moment, rather than the full definition of your life.
Then I’m a big believer in disclosure that we talked about it before and it is as exactly as you pointed out, Alison, it is telling that 15,000 people decided that they wanted to share a regret with a complete stranger, that tells us something. When I set up this survey and had people contribute their regrets, I gave them the option. I said, if you want to be contacted for a follow up interview, feel free to include your email address. Thinking that we get maybe 5%, 6%, we got 32% of people opted in to be contacted.
ALISON BEARD: That’s amazing.
DAN PINK: I know. Isn’t it. Yeah. It’s like, not only do I want to tell my biggest regret to a complete stranger, but I’m going to give him my email address so I can talk to him more about it.
ALISON BEARD: Right. It’s actually, I shouldn’t say it’s amazing because whenever I do something that I feel bad about, like I’ve made a social faux pas or messed up at work, the immediate thing I do is just tell as many people as I can about it. Just sort of like talk it out. And I tell my kids that. I’m like, if you do something wrong, it feels so much better if you just tell people about it. It’s almost like making fun of yourself.
DAN PINK: Exactly. Well, it’s more than that. It’s actually more profound than that, Alison, because what you’re doing is you’re unburdening. That’s very important. But the other thing you’re doing when we talk about our regrets, even write about our regrets privately is you are making sense of them. And here’s the thing. This is part of our problem with negative emotions. We don’t know how to deal with them. I’m glad that you’re giving that instruction to your kids. I wish that more parents gave those instructions to their kids because emotions in general are blobby and amorphous. That’s what makes positive emotions so wonderful. They glow, they’re abstract. They’re like these gauzy clouds around us. That’s why positive emotions feel so good. But it’s also why negative emotions feel so bad. They’re the abstraction that is kind of menacing.
And so when you talk about them, you convert that blobby abstraction into concrete words, and that makes them less menacing. So that’s what you’re saying when you say you’re making fun of yourself, you’re actually reducing the menace by moving it from abstract to concrete. And that begins the sense making process.
ALISON BEARD: And then we start to learn about what we would do better next time?
DAN PINK: Exactly. And that’s the next step would be to extract a lesson from it. And the way that we extract a lesson from it is by getting some distance from it. We are terrible at solving our own problems generally, but we’re not bad at solving other people’s problems. Because when we solve our own problems, we’re too enmeshed in the details. We don’t see the big picture, but when we solve other people’s problems, we can actually take a step back. So there are all kinds of techniques where you can, goofy things like talking to yourself in the third person.
Other things I really like is kind of making a phone call to yourself 10 years from now. So what does the Alison of 2032 wants you to do? Because she has your best interest in mind. But even my favorite decision making technique of any kind, forget about regret is if you’re at a juncture, you’re deciding what to do, ask yourself, what would I tell my best friend to do? I’ve been in so many situations where someone comes to me and say, “Oh, I don’t know what to do. I got to be…” And I say, “Well, what would you tell your best friend to do?” And they say, “Oh, well, I’d tell her to….” And I’m like, “okay, I think that’s what you should do.”
But we don’t see that because when we deal with our own problems, we plunge in like scuba divers. And what we should be doing is zooming out like oceanographers.
ALISON BEARD: This learning lesson piece of it, I completely get that, examine your past to make sure you do better in the future. But I do worry in that regard about unintended consequences, so people who regret not taking a risk before. And so then take one, they shouldn’t, or the opposite, you didn’t play it safe earlier. So now you play it too safe. Can that happen too?
DAN PINK: Absolutely. I mean. There’s no question about that because human beings are imperfect decision makers. But this is why it’s important to, when during that examination to examine the decision itself and the context you were in at the moment that I think is really important. So if you ask yourself, okay, I’m going to go back in time and say, “Ah, if only I hadn’t taken that job, I wasted two or three years. And it was just a disaster.” You have to look back on who you were when you made that decision and the information that you had and scrutinized the decision that way and really try to draw a lesson from that.
So it could be that you just didn’t know that you were completely taken by surprise, that you had done your due diligence, that you had researched the place that you were working. You had talked to people who had worked there and the situation changed, and there was nothing you can do about it. I think that learning that there isn’t a lesson is that self a lesson and prevents people from over-indexing and swerving from last time I didn’t take the risk. Now I’m going to play it safe. Last time I played it safe, now I’m going to take the risk.
ALISON BEARD: Yeah. And another thing that really struck me in reading the examples and case studies that you included in the book is how many people regret things that they actually have the opportunity to fix, particularly on the relationship level, even with regard to career things. You didn’t study abroad, so maybe take a job abroad. How do you get people to sort of move past that mindset of thinking about it and then doing something about it?
DAN PINK: Well, that’s a really, really great point. And I think part of it is-
ALISON BEARD: Like right now, I really regret letting my cat into this closet where I’m recording the studio and I can fix it theoretically by locking him out again. But it’s really frustrating. It’s my big regret from this interview. Okay. There he goes.
DAN PINK: Is the cat still in there? Do you need to get rid of it?
ALISON BEARD: There he goes. I’ve gotten rid of him and I hope he doesn’t scratch on the door again. Go ahead.
DAN PINK: So there you go. You’ve just been a very positive role model for dealing with your regrets. One of the things that was kind of in interesting is that when I was interviewing people, the story would change. So, there was a woman who I talked to who was resistant to reach out to this friend of hers from 25 years ago because she was very close to her in college and they drifted apart. And I was talking to her about why that was, and I did several interviews with her and at one point she emailed me and said, “Oh, I’m going to reach out to her.”
And I’m like, “Okay, all right. If you do that, let me know.” And then, but she doesn’t do it. And then, I actually write up her story and she says, “I just reached out to her.” Oh, great. Okay. Now your story’s changing. Oh. And she got back to me within two hours. I’m like, oh great. Here we go. The story’s changing again and says, now we’re having a virtual lunch. And so I think that reckoning with the regret, acknowledging it and disclosing it can be catalytic in that regard. It can actually show us that we can do something about it.
ALISON BEARD: Yeah. And I will admit that when I first saw that title of your book, I thought, “Oh, why didn’t you make it like avoiding regret?”
DAN PINK: Yeah.
ALISON BEARD: But I get the point. We’re not supposed to avoid it. It’s going to help us. At the same time, can’t we also look back at like the good moves that we’ve made or the good non moves that we’ve made and figure out what we got right. Instead of focusing so much on what we got wrong.
DAN PINK: You know, we have this crisis going on among people in high school and high school age and college age, young men and women who are being hobbled. And I think a reason for that is that we haven’t taught them how to deal with negative emotions. We haven’t told them that negative emotions are part of life and you can deal with them in a systematic way.
So what happens is that when they feel the sphere of a negative emotion, they think, oh my God, there’s something wrong with me. I’m broken. Everybody else is so relentlessly positive. I got a serious, serious problem and that can lead them to despair rather than to this, I think much more productive approach of looking at that word regret in big yellow letters on the cover of this book and saying, hello, regret. I’m going to stare you in the eye and I’m going to learn from you.
ALISON BEARD: So you talk about writing a failure resume, but your mention of college students makes me think that instead of those essays about all the accomplishments they’ve had, everyone should just talk about like all the terrible mistakes they’ve made and what they’ve learned from them.
DAN PINK: I mean there is a, I think that can get a little performative when someone says what’s your, it’s like those job interviews, what’s your biggest weakness. I care too much and work too hard.
ALISON BEARD: I’m a perfectionist.
DAN PINK: So I think that can get a little, I think that can get, yeah, I’m a perfectionist. I care too much about my boss. I treat my boss too well. We do everything my boss tells me.
But the failure resume is a brilliant idea from Tina Seelig and I’ve done it and it’s been very useful for me and essentially, it’s like a negative resume. You list all of your screw-ups, your failures, your setbacks, your mistakes. List, those in one column. And then in the next column, you list the lesson that you learned from it. And then you list what you’re going to do about it. And to one of your earlier questions, Alison, when I did this, it was really revelatory for me. So it listed all of the, and there were almost all, I didn’t go into personal mistakes in this one. There were enough professional mistakes to last me for a while.
What I realized was that for some of these mistakes and some of these setbacks, there actually wasn’t a lesson. Okay? Like the lesson was sometimes things don’t work out. The lesson was, the universe is random and you just don’t know. And that’s reassuring in a way, that’s reassuring in a way. What’s more is that what I discovered is that earlier, especially earlier in my professional life, I had been making the same two mistakes over and over again. Those mistakes rose to the surface when I started extracting lessons from the failure. So I found it an incredibly useful exercise. And it’s not public. It’s for yourself.
ALISON BEARD: Now I’m curious, what were the two mistakes that you kept making over and over again?
DAN PINK: Oh, I’ll happily talk about those. One of them was that in many decisions earlier, professional decisions earlier in my life, I went into jobs or other kinds of situations without knowing anything about what it was really like, about going in and making assumptions, going in without doing any due diligence going in and not doing any what’s called surrogation, looking for a surrogate. I’ll give you an example. I went to law school. It’s crazy. Alison, I went to law school, having never visited a law school. I went to law school, having never sat in on a law school class. I went to law school having never talked to a lawyer about what she did.
Like that’s ridiculous. I wouldn’t tell my own kids to do that. I wouldn’t do that in any situation now. So that was a big one. Overconfidence about what I knew and not doing the work.
The other one was actually committing to projects that I wasn’t 100% into. So I’ve had a couple of things flop and I realized, and I’m unpacking why they flopped, it was ultimately I didn’t care. And I wasn’t willing to give a hundred percent to it. And, it’s hard to get stuff done when you’re not giving a hundred percent. For me, at least it’s impossible to get good work done if you’re not in it all the way. And then that’s been a really important lesson for me in some ways, doing less and also in doing things where back to Derek Severs has this great heuristic where he says, “If it’s not a hell, yes, it’s a no.”
ALISON BEARD: Yeah. And you talked about workplace culture and how that can sort of force people into doing things that they regret. I wonder what advice you have for leaders or managers of teams about A, how to prevent that, but then B also to help their employees have a better mindset about the regrets that they do have professionally and the mistakes that they’ve made.
DAN PINK: Sure. On the first part, I think that a big part of it is actually thinking about these four core regrets as a photographic negative of what a good culture is. This chorus of now 18,000 people who are telling me what they regret most are also telling me what they value most. And it’s clear that if they value it in their lives, they should probably value it at work. What do they value? They value stability. So provide, fair pay and predictability. They value boldness. So provide psychological safety so people can be more entrepreneurial, take sensible risks, speak up. They value morality in being good. So be open and transparent and have a purpose. They value connection. So foster a sense of belonging.
Now on the second part, let’s go back to our old friend disclosure. I think that there is an important role for leaders to play in talking about their own regrets, because first of all, I think it’ll help them personally by disclosing their regrets and beginning the sense making process and extracting lessons from them. What’s more is that it will, I think, embolden other people to not bury their regrets, but to actually confront them themselves. I even am a fan of something called a regret circle where you gather, five people, six people, and you go around, each person talks about one regret and the other five help them make sense of it and extract a lesson from it. I think that’s a very, very healthy thing to do.
And what we know is that when we, it’s not a hundred percent the case, but it’s much more often true than not true, that when we disclose our vulnerabilities, our mistakes, our setbacks, people don’t think less of us. They often think more of us. And I think that’s a really important leadership lesson. And it sounds a little bit nutty, but so did vulnerability 10 years ago. 10 years ago, we weren’t really talking about vulnerability. Now, everyone and their brother-in-law is talking about vulnerability. And, and I think that’s a good thing. And this to me seems to be on the same kind of trajectory.
ALISON BEARD: Terrific. Well, thank you so much for coming on the show. I loved reading the stories. I loved learning about the research and it’s been great talking to you.
DAN PINK: Alison, always a pleasure. Thank you for having me.
ALISON BEARD: That’s Dan Pink, author of many books, including his latest, the Power of Regret: How Looking Backward Moves Us Forward.
If you enjoyed this episode, you can also check out our past interviews with Dan, that’s episode 339 called Why We’re All In Sales and a throwback to 2010 called What Motivates Us, that’s episode 183.
Listeners, we want to hear from you. This spring we’ll be airing a special series with Marcus Buckingham on How to Find Joy in Your Work. Head to hbr.org/ideacast/loveandwork to answer some questions about your own job. And you might just be featured in the show.
This episode was produced by Mary Dooe. We get technical help from Rob Eckhardt. Ian Fox is our audio product manager. Thanks for listening to the HBR IdeaCast I’m Alison Beard.
Regrets Are Inevitable. Start Learning From Them. – HBR.org Daily
How looking at past mistakes with a different mindset can help us make better decisions.