We all have regrets, though we often think it’s best not to. How can we learn from those regrets and become better versions of ourselves? Dan Pink, bestselling author, joins us for a conversation about his most recent book, The Power of Regret, which offers insights to help us become better leaders, managers, and marketers—and to also live healthier, happier lives. Dan’s original research, collecting stories of regrets from more than 24,000 people in 110 countries, shows how to transform our regrets into a force for good in our lives and in the world. Like his other books, The Power of Regret challenges conventional thinking and offers science-based insights and ideas you can put to use right away.


Doug Hattaway: Dan Pink, I know you are a man in demand, so thank you very much for joining us. First, let’s start with your story. You’re a writer, editor, and public speaker. You’ve got a great MasterClass on sales and persuasion, but you started out in politics and government. How did you go from there to where you are now? [Why] did you make this your mission to share these kinds of [regret-based] scientific insights with people?


Dan Pink: Well, I think like all stories of how we get to where we are, it is nonlinear. But to make a very long story short, I graduated from college, Northwestern University, worked briefly in Washington, and then I decided to go to law school, and I slogged my way through. I didn’t want to become a lawyer, so I started working on campaigns. And then somebody asked me to write a speech, and I did, and it was okay. They asked me to write another one, and then they asked me to write another one. You know how it works [in campaigns]. 

So I became a speechwriter working for the Clinton-Gore administration, working for the secretary of labor for a while, then working for the vice president, Al Gore, for a while. This wasn’t for me, and I realized I was always [writing] on the side. Out of nowhere [I was] in my early 30s, [and] it occurred to me that what I was doing on the side might be what I should be doing in the center. And so I decided to take a flier and write my own stuff, and I left my job. I went up to the third floor of our house in northwest DC, right near American University, and said, We’ll give it a couple of years; see if we can eke it out, and that was 20-plus years ago. Doug, if you had told me when we graduated from college together that I would be working from a garage, unshaven, writing a book, I think I would have been surprised.


Doug: Well, we’re glad you made the switch because your books really are insightful, useful, and fun to read. Tell us the story behind your recent book, The Power of Regret. Where did the idea come about, and how did you go about making this book?

Dan: It came out of my own experience where I was at a point in my life where, to my surprise, I realized I had mileage on me. I mean, it happens to all of us, where you suddenly realize, Oh my goodness, I’m looking backward [at my life], and there’s distance there. And when I—like anybody else—thought back, there were things I wish I had done, things I wish I hadn’t done, and things I wish I had done differently. It was kind of an unpleasant feeling, and I [thought] that nobody wanted to talk about it. But when I began talking with other people, I discovered that a lot of people [actually] wanted to talk about it. By bringing up this subject it unleashed this wave of emotion in people wanting to talk about regret. I started looking at some of the research on it, and realized that we had gotten this emotion profoundly wrong. 

Doug: And you conducted your own research?


Dan: So I did three pieces of research. The first was about the existing science on this emotion, from cognitive science, some neuroscience, a lot of social psychology, and some developmental psychology. I did my own very large public opinion survey, the largest survey of American attitudes on regret ever conducted. Then I also did something called the World Regret Survey, where I collected over 24,000 regrets from people in 110 countries.


Doug: That’s amazing. What’s a story from the book that exemplifies what you mean by the power of regret?


Dan: There’s a woman who I write about named Abby, who is 29. She lives in Phoenix, Arizona, and growing up, her grandparents, who lived in Indiana, would come to visit her in the winter. Abby hated having her grandparents around as a kid. She thought that they were annoying. She thought they were pestering her, asking her questions, and she really resented it. Then her grandparents passed away, and she realized when she got [into] her late teens: Oh, my God, I blew it. She didn’t hear anything about their lives, or their stories. She didn’t get to know them, and she felt really bad. And that’s the thing about regret—regret makes us feel bad. But by making us feel bad, it can, if we treat it right, clarify what we value and instruct us on how to do better. 

What Abby could have done is said, I have no regrets. It doesn’t matter. It’s in the past. I can’t do anything about it. Bad idea. She also could have said, I am the worst person in the world. I’m a horrible human being. I’m a terrible granddaughter. That’s a bad idea too. What she actually said is, This feeling stinks, but it’s telling me something. And what it’s telling her is that she didn’t want to blow it again with her parents. What she did next is she systematically began collecting the stories of her parents, so she would know those stories, and so she wouldn’t have this bad, sinking feeling later on. So here’s somebody who takes this emotion, and instead of ignoring it or wallowing in it, she uses it as a catalyst for deepening her values of love and connection. So she now has these stories from her parents that she will have, and maybe if she has kids, that her kids will have forever.

Doug: You said we have been getting the emotion [of regret] all wrong. Does that mean we should strive to live life with no regrets?


Dan: I think the aspiration of living life with no regrets is okay. What bothers me is when people say, No, I have no regrets, and [it’s often] quite performative, in my view. Here in America, we’ve been told that we should be positive all the time and never be negative. We should look forward all the time and never look back, and that’s a bad idea. That’s unscientific. We should have many more positive emotions than negative emotions. But negative emotions are functional. Negative emotions help us. When scientists have looked at our negative emotions, whether it’s fear, or guilt, or anger, or regret, the most powerful and potent one seems to be regret. There’s evidence that it’s the most common negative emotion that people experience. And we also have piles of evidence, particularly in social psychology, that if you deal with your regret properly, it helps us become better problem solvers. It can help us become better strategists. Regret is misunderstood in two regards: number one, it’s a very strong signal that we need to listen to; and two, if we listen to the signal and act on it, it can help us become better [people].


Doug: You mentioned guilt. Regret seems to be related to guilt in that it’s retrospective, and that guilt can also be a motivational emotion called a “self-accountability emotion.” It can help us hold ourselves accountable to our values and the kind of people we want to be. How are they related?


Dan: It’s a great point, Doug. I mean, it’s similar. So guilt, I would say, is a subset of regret. Guilt is a bad feeling we get from a moral regret, a moral inaction or action. In my research, there’s a database with huge numbers of people who wanted to ask a person out on a date, but they didn’t, and they regret it 20 years later. That’s not guilt. That’s a regret about a lack of boldness. 

I have four big categories of regret that people around the world seem to express, and one of them [is] these moral regrets. We’re often at a juncture in our lives where we can do the right thing or do the wrong thing, where we can take the low road or take the high road, and most of us, most of the time, regret taking the low road or doing the wrong thing. We might still do it, but afterwards, it sticks with us.


There are people in these 24,000 [responses] who regret and are really bothered by bullying people 40 years ago. One said they regret stealing from a store something like 60 years ago. I think what it suggests is that most of us actually are good and want to be good, and that when we’re not that way, we regret it. And when we feel that guilt, it’s telling us something. It’s saying, Hey, I actually value honesty. I value kindness. It’s clarifying what we value, and it’s instructing us what to do in the future because it’s saying, I don’t want to feel this way again, so I better do the right thing next time.


Doug: Let’s hear about the other three. So there’s the moral regrets you just gave examples of. What are the other three categories?


Dan: One is what I call “foundation regrets.” These are small decisions that people make early in life that accumulate to negative consequences later in life. One of the most common is I spent too much and saved too little, and now I’m broke. No single action leads to this regret. Going out to dinner once is not going to destroy your life. There are a lot of these regrets about health. Again, skipping a day of exercise or eating some junk food today isn’t cataclysmic, but you do that cumulatively and it adds up. We have more [foundational regrets] than I expected about education. People who blew off their education and now said, Whoa, wait a second. I don’t have the skills, and this is a hard problem for me to address. So foundation regrets are If only I’d done the work

“Boldness regrets” are a big category. Again, you’re at a juncture: you can play it safe, or you can take the chance. And the people who don’t take the chance—most of the time, more than I expected—regret it. And it doesn’t matter the domain of life. I mentioned, like romance, just asking somebody out on a date—I was shocked by how many of those that I have. And these [regrets] are like 30 years ago. You also have people [who] had a chance to travel or go on an adventure and then chickened out, and now they regret it. You [Doug] started a business. There are all these people out there who regret not starting a business. And so boldness regrets [are] If only I’d taken the chance

And finally, [there are] connection regrets, which are about relationships that were intact or should have been intact. These relationships come apart usually in undramatic ways. Somebody wants to reach out, [but] they feel awkward about doing that. They think the other side is not going to care, so they don’t reach out, and the drift goes even further. And so connection regrets are If only I had reached out

And what’s pretty amazing about this, at least to me, is how similar these regrets are all over the world. If I were just to randomly pick 10 regrets from this database, I don’t think you’d be able to tell me where they’re from. I don’t think you’d be able to tell me, is this from Wisconsin, or is this from Portugal, or is this from Malaysia? I mean, it’s that degree of commonality. It really surprised me.


Doug: Yeah, they do all sound like the human condition. I’m like, oh, wait, I’ve checked all those boxes. And amazing to hear you say— it’s not just me who regrets something I said that I shouldn’t have said, or not saying something I should have said 30 years ago.


Dan: Amen. I think that one of the takeaways here is—again, I don’t want to sound like that old ride at Disneyland where it’s like, It’s a small world after all, where you’re going down a boat and they’re singing that horrible song—but… we do have this common set of experiences. 

I think you had the right phrase—regret teaches us about the human condition. And it’s surprising, too, because we say, Oh, I don’t want to talk about regret. I don’t have any regrets. And yet, if we take this emotion, and not get [freaked] out by it but just examine it, it’s telling us about the human condition. It’s telling us what constitutes a good life. Because when people tell you what they regret the most, they’re telling you what they value the most. If you don’t have a regret from something you did or didn’t do 30 years ago, that’s a very strong signal. Regret is a very strong knock at the door. So answer the door and see what it’s telling you.

To hear the full version of this story, tune into our Achieve Great Things podcast.