What Is the Power of Regret? A Conversation with Daniel Pink

Years of working in the behavioral sciences have given me a different view of the many missteps and mistakes that I’ve made (and continue to make). I now view them with a more positive frame than the traditionally negative one of “regret.” But reframing the feeling of regret doesn’t make one immune to it.

I’ve often wondered what makes the actions (or inactions) that we come to see as mistakes feel like moments of growth rather than moments for which we’d give anything for a do-over. Why and how is regret triggered, and for whom? How do you get over it? Is there such a thing as good regret? And what role does regret play in how we understand our lives and shape them for the future?

In The Power of Regret, author Daniel Pink investigates these questions and offers readers a glimpse into the psychology of those moments that we often wish we had back. I invited Pink to discuss the book, and you’ll find our conversation below, edited for length and clarity. We discussed his World Regret Survey, which has cataloged over 23,000 regrets from people around the globe, the four core regrets, and how regret, while painful in the moment, can help us move us forward.

Josh Wright: Dan, you’ve written a number of books related to psychology and behavioral science: A Whole New Mind, Drive, To Sell Is Human, When, and now The Power of Regret. Can you share a bit about why you decided to write about regret and why now?

Daniel Pink: For me it was personal. I found myself at a moment in my life when I had mileage on me. To my surprise, I had room to look back. And when I looked back, I realized that there were some things that I regretted doing and others I regretted not doing. The curious thing about it is that when I very sheepishly began talking about some of these regrets to people in private conversation, I got a surprising response—people were really interested in engaging; they wanted to share. It’s almost like this dam burst.

Can we make sure we have a working definition of what we mean by regret, so we’re on the same page?

First of all, regret is an emotion. It’s a negative emotion in that it’s an emotion that makes us feel worse, not better. And it’s an emotion that’s triggered when we think of something from our past and wish we had done something differently, done something in a different way, not done something, taken an action, not taken an action. It’s incredibly cognitively complex because it requires mental time travel. You have to get in a time machine in your head and travel back to the past. Then you have to imagine the counterfactual to what really happened, and then get back in your time machine, come back to present day, and see the present day reconfigured because of the decision you made.

When I very sheepishly began talking about some of these regrets to people in private conversation, I got a surprising response—people were really interested in engaging; they wanted to share. It’s almost like this dam burst.

Was there any particular insight that stood out to you from the quantitative research regarding demographics and regret?

The big surprise was that there weren’t that many demographic differences. I had two big takeaways from the quantitative survey. First, we asked people a question about regret without using the R word—we were trying to get past this fog machine of “no regrets.” We asked, “How often do you look back in your life and wish you had done something differently?” And we found 83 percent of the population is saying they do that, at least occasionally. It verifies how common this emotion is, especially when we don’t label it with that toxic word.

Second, the big demographic difference, and I think it’s actually pretty profound, was on age. It showed that when people are young—say, in their 20s—they have roughly equal numbers of regrets of action (what they did) and regrets of inaction (what they didn’t do). But as we age, as quickly as the 30s and certainly 40s, 50s, 60s, 70s, the inaction regrets take over. Inaction regrets are, in general, about twice as prevalent as action regrets. As we get older, what really sticks with us are the regrets about what we didn’t do.

You collected all these amazing stories from people. Was there a story or two in particular that were your favorite or that helped you have a new perspective on regret?

I set up a website called The World Regret Survey, and to my amazement, with just a couple of tweets and a newsletter mention, we ended up very quickly with a database of 15,000 regrets from more than 100 countries. Now we have more than 23,000 regrets from people in 109 countries.

What really stuck with me were the stories about people in relationships that had drifted apart who didn’t reach out. And then in some cases it was too late, and in other cases, it was just bugging them the whole time. As I interviewed these people, especially people for whom the door was still open, I would actually become frustrated. “What are you doing? Just call the person! Reach out!”

But then I thought of the proverb “Physician, heal thyself.” I realized, Wow, I don’t take my own advice on that. And for the exact same reason. Those stories changed both my perspective and my behavior. I’m not somebody who’s been super good about reaching out. Now my own mode as a human being is that if I’m at a juncture where I’m saying, “Should I reach out or should I not reach out?” I know the answer.

Always do it.

Always reach out.

Do people generally not feel comfortable talking about regret? Are there things that we could do to get people to talk about regret and make it more socially acceptable?

In my experience, there’s a kind of pluralistic ignorance here. We believe that no one else has many regrets, and certainly if they did, they wouldn’t want to mention them. So we think that we should be that way too, even though we actually desperately want to talk about them—because talking about them is a way of relieving the burden. Talking about them is a way of making sense of those regrets.

When people are young, they have roughly equal numbers of regrets of action (what they did) and regrets of inaction (what they didn’t do). But as we age, the inaction regrets take over.

Let’s go back to this survey. The mere fact that, almost instantly, 15,000 people wanted to share their big regret with a complete stranger itself is revealing. What’s more, something like 32 percent of people agreed to share their email and opt in to be contacted. They said, “Not only do I want to share my regret with a stranger, but I’m going to give him my email address so he can talk to me more about the regret.” Again, people deeply want to talk about this. And they’re looking for their permission, or they’re looking for a role model. They’re looking for someone to part the curtains.

There’s something there probably for ideas42 (the nonprofit I run) and other organizations to think about, about the benefit of getting people to talk about their regrets, and how that could be a powerful tool for connection.

Yes, if we talk about them the right way. I mean, there’s talking about them and talking about them. You can talk about them and say, “Oh, my God, I’m the biggest loser that there was, I can’t believe what an idiot I am, I never do anything right.” That’s not a healthy way to talk about your regrets! But you could have people in positions of leadership who say, “Hey, everybody, today I want to tell you about one regret that I have, I want to tell you what I learned from it, and I want to tell you what I’m going to do about it.” I think that is an incredibly powerful, perhaps transformative, conversation to have in organizations.

Yeah, absolutely. And it’s in line with how we might assume that other people don’t have the same feelings that we have, when reality is, we’re all much more alike than we are different.

Exactly. That is so true. We’re so over-indexed on our specialness. The World Regret Survey, unlike the second research project I undertook, the American Regret Project, wasn’t a random sample, so I can’t make strong claims about differences based on nationality. But if I gave you 10 regrets from our database and asked you to tell me whether this person was American, not American, I doubt you could. You might be able to tell me a little bit about whether they were old or young. But male or female? Probably not. I mean, it’s really quite incredible.

People deeply want to talk about this. And they’re looking for their permission, or they’re looking for a role model. They’re looking for someone to part the curtains.

The book is organized around four core regrets: foundation regret, boldness regret, moral regret, and connection regret. Is any one of these regrets more powerful than others in how we can reflect on or use them to be happier humans in the future?

I came up with these four core regrets from the qualitative survey by reading these initial 15,000 regrets. What I realized is that the way that I and many others had categorized regret was insufficient. In my quantitative survey, I had people slot their regrets into categories like career, education, romance, health. I realized when I started reading through these regrets that there was something else going on.

Here’s an example. If you have somebody who regrets not studying abroad in college, that’s an education regret. Somebody who regrets not asking somebody out on a date, that’s a romance regret. Somebody who regrets not starting a business, that’s a career regret. But all those regrets are the same. Those are regrets about not taking the chance. Those are regrets about being at a juncture and choosing to play it safe rather than taking a chance. So if you have people who regret cheating on their spouse, that’s a romance regret. If you have people who regret cheating in school, that’s an education regret. You have people who regret cheating their business partner, that’s a career regret. But they’re all regrets about cheating.

They’re all moral regrets.

Right. The surface domain matters less than—and this is where the linguistics comes in, because I talk about linguist Noam Chomsky’s theory of language—deep structure, which is, I think, more revealing. What I found are these four core regrets: foundation, boldness, moral and connection. Now, is one more prevalent? I don’t know, but the category that was biggest was connection regrets—“If only I’d reached out.” These regrets are about relationships that were intact, or should have been intact, that come apart, usually in slow, undramatic ways. People want to reach out, but they fear it’s going to be awkward, and they think the other side is not going to care. So they don’t reach out, and then things drift even more. And as more time passes, we believe it’s even more awkward to reach out. Connection regrets were the biggest category of those four deep structure regrets.

One of the nice things about that is, unless the person has passed away or is unreachable, it’s a regret that’s reversible, right?

Absolutely. You can address it. It’s an inaction regret, and you can act. Now, there’s some sad stories in the book where the door has closed, and people couldn’t act. With those, you have to actually feel that spear of pain and say, “Okay, I blew it this time. I gotta do better next time.”

Disclosure: Josh Wright is the executive director of ideas42, which provides financial support to Behavioral Scientist as a Founding Partner. Dan Pink a member of the Behavioral Scientist’s Advisory Board. Founding Partners and advisors do not play a role in the editorial decisions of the magazine. Cameron French, an editor at Behavioral Scientist, served as an editorial consultant on The Power of Regret.