Dan Pink Talks About "The Power of Regret"

"No Regrets" is a popular tattoo but a bad mindset. In this week's episode of Motley Fool Money, host Chris Hill talks with best-selling author Dan Pink about his new book The Power of Regret: How Looking Backward Moves Us Forward. Dan shares how we can apply the feeling of regret to improve our lives. In this conversation with Motley Fool host Chris Hill, Dan also discusses:

• The research project that led to people around the world sharing their own regrets.
• How reaching out to old connections is never as awkward as you may think.
• The future of offices and remote work.
• His personal experiences with comedian Bob Saget.
• The potential of no Major League Baseball season this year.

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. To get started investing, check out our quick-start guide to investing in stocks. A full transcript follows the video.

This video was recorded on Jan. 30, 2022.

Dan Pink: Never looking backward is a colossal and stupid idea. What you want to do is you want to look backward, but you want to look backward in a particular way that allows you to understand your choice, unburden yourself of that choice, extract a lesson from that choice and apply going forward.

Chris Hill: I'm Chris Hill, and that was Dan Pink, author of multiple best-selling books, including Drive, To sell Is Human, and When The Scientific Secrets of Perfect Timing. His new book is The Power Of Regret: How looking backward moves us forward. I wanted to talk with Dan about his book and since he's written about the business world, I also got his thoughts on where companies are going with office space and hybrid work. Since I know he's a sports fan, I also asked him to say the major league baseball season. I know that probably wasn't fair of me to ask since he's not actually involved in the negotiations between baseball owners and players, but I don't regret asking. Until I read Dan's book, I never really thought of regret as being something with great power. I started by asking him what got him interested in this topic?

Dan Pink: I think it was mostly because I realized that I had regrets of my own. If there was a catalytic moment and you can certainly relate to this with two kids in college is that my elder daughter graduated from college in 2019. I'm at her graduation and I'm having this out of body experience where I can't believe this kid is old enough to graduate from college. I also can't believe that I have a kid who's graduating from college because I'm 24. [laughs] I'm having this out of body experience and I'm thinking about, what was my college like? I started thinking about all these regrets that I had. That I didn't work hard enough. That I didn't take enough risks. One that really bugs me is that I felt that wasn't kind enough. When I came back, I just sheepishly mentioned it to a few people. Instead of their recoiling, people leaned in, which to my surprise, they really wanted to talk about this. That's an interesting reaction for a writer. It's a really interesting reaction, especially when you come up with a topic that you think isn't going to go over that well, and people instead just glam onto. I started looking at some of the academic research on it. I ended up actually putting aside a book that I was writing at that moment and spent a month researching regret and then wrote an entirely new proposal and had to go to my editor and say, "I got some good news and some bad news. The bad news is the book you think I'm writing, I'm not going to do that anymore. The good news is that I think I have something better."

Chris Hill: I did have that thought because, you and I have talked about this before, I remember talking to Scott Galloway about this, it doesn't matter how successful a nonfiction writer is, when they go [laughs] to their publisher with, here's my idea for a book. As often as not the publisher would be like, "Oh, God really? You want to do that?" There's no trust in the track record, so it's nice to know that they responded the way they did. As you indicated, there is a lot of research on this topic, you get to some of the research in your book. But you did research of your own. Can you share your thought process around the research that you originated and how you went about it?

Dan Pink: Sure thing. I'm glad, and thanks for asking about that because I'm really psyched about that. I did look at about 50 years of research. Mostly in social science, some neuroscience and medical science on regret. But I also did two projects of my own. One of them was something that I called the American regret project, where working with a company called Qualtrics, I put together the largest public opinion survey of American attitudes on regret ever done. We served a 4,489 Americans beautiful, gorgeous representative sample. To ask a whole bunch of questions about American attitudes about regret, in part to try to understand what demographic differences there were. At the same time, I did something else which I called the World Regret Survey, where I basically just set up a website and invited people to contribute their regrets hoping to get several 100. Well, we're over 17,000 now [laughs] so I ended up with 16,000 regrets from 105 countries. Those proved just an incredible source of insight and emotion and in a weird way, inspiration.

Chris Hill: You include some of them in the book. Every chapter begins with a few regrets that actual people have sent you. I was struck by the fact that there's such an enormous range of things that people regret. Some people regret at what on the page seem like very big decisions. But I was really struck by the people who have a regret of something they did long ago, and it seems like a small thing, and yet it's stuck with them. Maybe that gets to the power of regret that it doesn't matter how small it is, it can stick with you.

Dan Pink: You know what? It's a fascinating insight that you're making there because very few people talked about regrets in terms of their size. The fact that it happened and it was meaningful to them is enough. I think what's interesting is, and I think your insight is really powerful here, while there is a wide variety of regrets about the domains of life. One of them that really stuck with me was a 70 something year old woman in New Jersey who regretted stealing candy when she was a kid, 60 years later, she's still bugged by that. We're people with regrets about careers and health and romance and family and so forth. They run the gamut of the whole human experience. But what I found in looking at that giant trove of regrets was a deep down, around the world, it's amazing, people kept expressing the same four core regrets over and over again, irrespective of the domain. That took me to a place through this avenue of regret that I didn't expect to reach.

Chris Hill: This is where you and your team really build on the research of the past 50 years with categorizing the four types of regret; foundation, boldness, moral, and connection. If you can, did that just become apparent over time like, oh, we're starting to see this pattern and it breaks into these four groups?

Dan Pink: I'd love to tell you a story of how I bolted up right in the middle of the night and had this epiphany about the four core regrets. But it was much more undramatic and laborious than that as I was just reading through these regrets and trying to categorize them and thinking of categories on the whiteboard. But the other thing is that these two different pieces of research work together. For instance, when I did the quantitative survey, I thought I was going to get at the question of what people regretted. I had them categorize their regrets by domain. What I found is what researchers have been finding for 50 years is that they regret a lot of things, just as you're saying, they span, and I said, "God, that's so unsatisfying." I started thinking a little bit differently about the qualitative regrets. There I started seeing some patterns. Let me give you an example because I think that it makes more sense in the specific. I know that a lot of the Fools are entrepreneurs, so I'll give you an entrepreneurial idea here, Fools. Start a travel agency that serves people who went to college who regretted not studying abroad. I've got hundred of those, so think about that regret. 

That's called out an education regret. Then I've got people, hundreds around the world who have a regret that says, "I've always wanted to start a business, I've always wanted to go out of my own, but I never had the guts to do it." That's a career regret. Then I have once again, hundreds around the world, almost with the exact same formulation, "X years ago, I met a man/women whom I really liked. I wanted to ask him/her out, but I was too chicken to do it, and I've always regretted." That's a romance regret. But to my mind, as far as you started seeing this, those are all the same regret. Those are all regrets about boldness. Those are all regrets about being an injunction on your life and having a choice. Do I play it safe or do I take the chance? When people play it safe they often regret it, not always and when they take a chance they don't always relish it. But it's pretty overwhelming that we regret not taking that chance. That's boldness regret. To meet all these four core regrets reveal something, I mean, again, it's weird, Chris, because I didn't expect to go there. But all these four regrets in a way reveal what makes life worth living and one of the things that makes life worth living, one of the components of a good life is doing stuff, trying stuff, learning, growing, leading a psychologically rich life. Boldness regards are one of the really most significant regrets that people have.

Chris Hill: I think that's probably the category that most stock investors can identify with. Because the two of the biggest regrets when it comes to investing are, I should have bought this stock earlier or I should not have sold this stock and the reason we don't buy the young upstart on profitable company is because of the risk factors involved it. The reason we sell that young, unprofitable upstart company after it gained 30 percent in the year is like [NOISE]. This isn't good. It's playing it safe instead of being bold.

Dan Pink: I think in many ways these four core regrets go to not only how we invest, but to some extent why we invest. A good example of it, and would you see over and over again, I mean, I think anybody who's listening to this probably doesn't have many in this first category, foundation regrets. Boldness regrets are if only I'd taken the chance. Foundation regrets are if only I'd done the work. What that means is people who regret not studying hard enough in school, a lot of those. Smoking, huge numbers of people regard smoking, not taking care of their health, and not saving money. One of the things that comes out with, I mean, obviously fools know this is the power of compounding interest in both the literal and metaphorical sense. Foundation regrets are these things where you make small decisions early that seemed to have no huge consequence, but over time they accumulate and then they become unstoppable. 

I have one guy who I found very pointed who said, I mean, he says, "I regret not saving money diligently ever since I started working." He's 43. It's nearly crushing every day to think how hard I've worked over the last 25 years but financially I have nothing to show for it. What does that tell us though? I think it's something full investors understand is that an element of a good life is stability. We want to have some stable platform when our lives are unstable when our lives are chaotic and unpredictable, that drains our ability to lead a satisfying life. Financial markets are a challenging one because the nature of regret requires some agency on the part of the person who has the regret. They have that regard as your fault, not someone else's fault. But with foundation regrets it can be challenging. It's hard to save if you graduate from college, burdened with massive student loans. It's harder to do well in university if you went to a secondary school that wasn't very good. With foundation regards, we have to be a little bit careful with agency, but they're really important. Having that stable foundation is extraordinarily important to people.

Chris Hill: Let's get to a couple of things in the book that are again the subtitle how looking backward moves us forward. Because there's a lot of research you get to you in terms of regrets that are by nature looking backward. But one of the great things about your book is that it provides us with insight on tools of, don't just look backward with regret. Here are the tools to look forward and make better decisions. Once you get to is an example we've talked about on the show before, you categorize it as self-distancing. The example we've talked about before over the years on this show is Andy Grove, the former CEO of Intel, that was faced with the decision of basically walking away from a profitable division of the company and investing in new technology and weighing that decision and then he turned to a trusted lieutenant, and said, "If you and I got fired, the people who replaced us, what would they do?" His lieutenant was like, "They would absolutely invest in this new technology." He's like, "Great, that you're right. That's what they would do. That's what we should do."

Dan Pink: That is one of the most important elements and how we deal with our regret at a big picture. We have to do some triangulation with our regret. You can say, we have this philosophy out there, no regrets, which is nonsense because you can say, however, regret, "It doesn't matter. I always look forward. I never look backward." That's a bad idea. Regret exists for a reason, regret isn't structured. If you do that you're never going to learn anything. On the other hand, some people over-index on their regrets and ruminate over them, wallowing them. In some cases, use the regrets as a way to exonerate themselves from doing something. That's a bad idea too. What you want to do is you want to use your regrets as signals for thinking and one way to do that is exactly as you say with self-distancing is, take a step back and say, "What did I learn from this and how can I apply that moving forward?" As you say, Chris, there's a pile of research showing that we're better off solving other people's problems than our own problems. What we want to do is give ourselves some distance from those and then some really clever, interesting tactics like that. For you Chris, if you wanted to deal with your regret, you could say, not what should I do, but what should Chris do? Talking to yourself and a third person, amazingly enough, seems to have that power. 

Going forward in time and saying, "Hey, 10 years from now, what decision will I have wanted to make?" The replacing yourself that Andy Grove talked about is powerful there too. One of my favorite techniques and something that Tennessee Liggett, Stanford University calls a failure resume, which is to put together a resume of your failures. We don't have these resumes in LinkedIn profiles that say that we're the greatest things since sliced bread and that we probably deserved both the Heisman Trophy and Oscar earlier in our lives. These things they just glisten. If you look at people's resumes they just shine. That's part of us, but it's not all of us. The flip side of that Tina says, is to create a failure resume which is a glorious compilation of your screw-ups and your setbacks and your failure. I did this myself, listed the mall. It's not pleasant. But what I did, but you have to do it systematically as you say, so I listed those things and then I said, what did I learn from this stuff, and how am I going to apply forward? For me, it was regulatory because I found that a lot of my mistakes keep coming back to the same two core blunders that I was making and I've more or less stewed around those in the future.

Chris Hill: The self-distancing is such a great strategy. I have to confess though. I was surprised to reading your book to see the comparison between Julius Caesar and Elmo. [laughs] I was not [laughs] expecting that. [laughs] Well you're right. Those are Julius Caesar, Elmo, they're big for referring to themselves in the third person.

Dan Pink: They both talk about themselves in the third person and so spanning a long amount of time, and arguably a span of species suggested that this technique is somehow useful to us. This is actually an important thing and how we analyze human beings. It's like we think about something like regret. Regret is the second most comment emotion that people express overall, it's the most common negative emotion that people express. Why is that? It must serve some purpose. All of us wouldn't be feeling bad if there wasn't a reason for it. The reason for it very clearly in the research is that if you deal with it right, it's instructive, it points a way forward and so never looking backward is a colossally stupid idea. What you want to do is you want to look backward, but you want to look backward in a particular way that allows you to understand your choice. Unburden yourself of that choice, extract a lesson from that choice and apply going forward.

Chris Hill: Is part of the process trying to do a better job in setting our own expectations? I just think about the research you have in your book around Olympic athletes and in particular Olympic medalists, and how across-the-board people who win the bronze medal are happier than people who win the silver medal, even though the silver medal is a greater achievement. But the bronze medal is in some cases, it's people who are just happy that they got a medal at all.

Dan Pink: Yeah.

Chris Hill: Maybe expectation setting is a part of that.

Dan Pink: It is a big part of that. What that shows is that again, our cognitive machinery is programmed for that counterfactual thinking. There're two different ways to do that counterfactual thinking. One is to imagine that things could have been better and that hurts. That's what regret is, but it's instructive. The other one, which is actually an OK tactic sometimes is to imagine that things could have turned out worse. An upward counterfactual regret is what I call and if only, but the downward counterfactual, how it could have turned out worse isn't at least. The silver medalists are saying, if only I had, I talked about a bike race in the bulk. "If only I'd pedal a tiny bit harder, I don't want to go rather than a silver." Whereas the bronze medalist is like, "Oh my God, at least I didn't slip from the lead like that other rider, and lose out on the medal stand altogether." 

I described this race which I didn't see live, but I saw a video of it. When they come over the finishing line, the silver medalist who just play second in the Olympics, she has a face buried in her hands, and the bronze medalist is exorbitant. This tells us something now, how do we apply that going forward for certain regrets particularly the regrets action. We can use that at least mechanism. I sell that a lot in the database of regret. Basically finding a silver lining, that can make you feel better. It doesn't necessarily mean that you do better, but it can make you feel better, and feeling better is OK sometimes. The most common one of that [laughs] in the database was, once again, dozens if not hundreds of people, I think they were all women, who said, "I really regret marrying that idiot, [laughs] but at least I have these two great kids." That's a silver lining. You can take certain kinds of regrets and at least them. Certain kinds of action regrets you can also undo. You get a tattoo and you're like, "That was a stupid idea." You can have the tattoo removed.

Chris Hill: One of my favorite stats in your book, that [laughs]for all the people touting they have no regrets, the tattoo removal business in America is a $100 million a year business.

Dan Pink: Yes. Maybe your analyst should be looking for a publicly held tattoo removal technology.

Chris Hill: When you and I talked about your last book, When: The Scientific Secrets, you said the research changed the way you live your life. When you make medical appointments, for example, they are always in the morning. By the way, having read your last book, I'm the same way, all medical appointments are before noon.

Dan Pink: All important medical appointments. I'll do a routine teeth cleaning in the afternoon. Because I think your listeners want to know this, I actually scheduled my next teeth cleaning for 8:00 AM, in case you were wondering about my dental hygiene here.

Chris Hill: Good to know. Has your work on this book, the research you've done, any changes for you personally?

Dan Pink: Yeah, several. I'll tell you the biggest one, it has to do with connection regrets, which was the biggest category of regrets. Connection regrets are if only I had reached out. I heard so many stories all over the world of people who had a relationship or should have had a relationship and it came apart. Not romantic relationships, but relationships with parents, or kids, or siblings, or other relatives, or friends, my gosh Chris, so much stuff about friends. These relationships come apart in profoundly undramatic ways. They just drift apart. What happens is someone says, "I should reach out but it's going to feel really awkward and the other side won't care." They're wrong. 

They're flatly wrong on both counts. It's less awkward than you think, and the other side almost always cares. For me, the big takeaway, and it's one of the things I'm actually trying to work on this year, is to just reach out more to people who we're friends, who I knew, who I liked, who were part of my life at one point. I've always resisted that because I was like, "It's going to be really awkward, and they're not going to care for that year for me." This disabused me of that, to the point where my advice to myself that I'm trying to follow, but also to others, is that if you get to a juncture in your life and you're asking yourself, "Should I reach out?" The answer is yes. If you've gotten to that juncture, you've answered the question. I think to me a huge takeaway from hearing all these regrets from around the world is always reach out.

Chris Hill: You've written about the workplace, you've written about what motivates executives and employees, and we're at a point in time where so many companies are trying to figure out how to manage employees in a increasingly remote world. I know you are a naturally curious person, so what are you seeing in the stories you read about the future of the office and work culture, and where do you think this is going?

Dan Pink: As for where it's going I have no idea. But I actually think that this question of remote versus on-site is a proxy for bigger questions that have been unresolved and actually never addressed in the way we navigate organizations. Let me give an example of this. What kind of work should be done together and what kind of work should be done solo? We don't have a good theory of that. We have been making it up since white-collar work began. We do not have a good theory of what should be collaborative and what should be alone. What kind of work should be done synchronously and what should be done asynchronously. We don't know that, we just have this habit of having synchronous meetings all the time. Big question that you alluded to, what is an office for today? I think that that is a huge question that is up for grabs and we need to seriously think that. I think there are bigger questions too within the great resignation. It's, what do companies owe employees, what do employees owe companies? This is a question that the Fool has been addressing through conscious capitalism, which I think becomes more and more important each year. I actually even think that these regrets give us some clues about effective organizations. When we think about what people want, what do they want? They want a stable foundation. We know from regret, they want a stable foundation, they want a chance to learn and grow, they want to do the right thing, and they want connection and love. In a way those are the building blocks of a coherent culture: a culture that provides a sense of belonging, a culture that does the right thing, a culture that has a sense of purpose, a culture that fosters a sense of belonging, a culture that allows people to take sensible risks. Even though this has been a tough two years for everybody, I'm actually surprisingly optimistic about what's going to happen once we turn the page. I do feel that we could be in for a significant reboot. I hope so.

Chris Hill: Two more things and then I'll let you go. Recently there was an outpouring of sadness over the passing of comedian Bob Saget, who in addition to being respected and beloved in the entertainment community was very much a doppelganger for you. You could've been Bob Saget stunt double. Did you ever cross paths with him and connect in any way?

Dan Pink: Well, Chris, so I did cross paths with him about, more in a moment. But before I crossed paths with him, I probably had people tell me that six, seven, eight times a year. I would be on an airplane and the flight attendant would say, "You know, you look a lot like Bob Saget." I'm like, "Okay, thank you." Anyway, I ended up doing a small project with him not that long ago, where we were playing around with a podcasting technology and experimenting with new ways to do audio shows. He and I got together to do something where we just took basically listen to your questions about what's your problem. I got a chance to prep with him and I got a chance to work with him a little bit. I have to say, it's almost cliche to say after someone has passed, but he's just a lovely guy. Here's this guy, he's a huge star, huge, recognized around the world, and he was on the prep calls before me. He was as kind and generous to everybody at every level all along the way. In the way that we dealt with questioners, I expected him to be funny, totally, he was, he was incredibly insightful, and incredibly empathetic. One of the things that you see is that all of us at some level are performing, especially actors. Sometimes somebody performs a role and underneath they're an ass. This was almost the exact opposite, that his public performance was more of like, "Hey, I'm going to tell some dirty jokes." But deep down, again, in my limited knowledge of him, he was just a very kind, warm human being. I was devastated when I heard it.

Chris Hill: I know you're a baseball fan, particularly the Washington Nationals. As of right now the season is in jeopardy because the owners of major league baseball teams and the players association have not come to a collective bargaining agreement. This would not be the first time baseball season was threatened. If you could stand in a room and deliver a message about the power of regret to the owners and the players association, what would you say?

Dan Pink: It's a great question. In the last baseball strike I was actually working at the United States Department of Labor for the Secretary of Labor. At one point I said, "You know what, maybe I can just strap on my Superman uniform and solve this strike." Of course that was a year that the world series had canceled. [laughs] What I would say is maybe do a little bit of the self-distancing, but it's a self-distancing in time. Ten years from now, how do you want to look back on this decision? If you're an owner, do you want to look back and say, "In my effort to squeeze out every last cent, I shut down the national pastime and disappointed kids all over America, and perhaps threatened the long-term health of the sport." With the players, who I'm actually more sympathetic to, I would say, "Listen, I understand where you're coming from, but remember that, I want you to do the same thing. Look back 10 years from now, and what do you want your kids to say about you? How do you want your kids to view this?" I think that that distancing in time can help them, not perfectly, but help them reach an agreement.

Chris Hill: The book is The Power of Regret: How Looking Backward Moves Us Forward. It's available everywhere you find books starting on February 1st. That's all for today. But coming up this week, we got a lot in store, including value investing, the Nasdaq, big tech earnings, from Alphabet, Amazon, Meta Platforms, and more. As always, people on the program may have interest in the stocks they talked about. The Motley Fool may have formal recommendations for or against, so don't buy or sell stocks based solely on what you hear. I'm Chris Hill, thanks for listening. We'll see you tomorrow.