The Power of Regret with Daniel Pink | PoP 665

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A photo of Daniel Pink is captured. Daniel H. Pink is the author of seven books, including the forthcoming The Power of Regret: How Looking Backward Moves Us Forward. Daniel Pink is featured on Practice of the Practice, a therapist podcast.

Why should you always try to “reclaim” your regrets? How can regret deepen meaning? Can feelings of regret boost performance and connection?

In this podcast episode, Joe Sanok speaks with multi-award-winning author, Daniel Pink, about the Power of Regret.

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Meet Daniel H. Pink

A photo of Daniel H. Pink is captured. Daniel is the author of seven books, and a journalist. He is featured on the Practice of the Practice, a therapist podcast.Daniel H. Pink is the author of seven books, including the forthcoming The Power of Regret: How Looking Backward Moves Us Forward.  His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human. Dan’s books have won multiple awards, have been translated into 42 languages, and have sold millions of copies around the world.

He has been a contributing editor at Fast Company and Wired as well as a business columnist for The Sunday Telegraph. His articles and essays have also appeared in The New York TimesHarvard Business ReviewThe New RepublicSlate, and other publications.


Visit Daniel Pink’s website. Connect with him on Facebook, Twitter, and LinkedIn.

Read Daniel’s award-winning books!

In This Podcast

  • Regret reclaimed
  • How regret boosts performance
  • Regrets revealed
  • How to deal with your regrets
  • Daniel’s advice to private practitioners

Regret reclaimed

Regret makes us human. Everybody has regret, and we have to normalize that. The problem isn’t that you feel regret, the problem is if you don’t feel any regrets, that’s a warning sign … but what you have to do is use those regrets properly. (Daniel Pink)

There is nuance in “reclaiming” your regrets. You can take your regrets and dismiss and ignore them, but that is a bad idea because this leads to illusion.

You can take your regrets and make them so bad that you exonerate yourself from dealing with them or taking responsibility, which is a bad idea as well because this leads to despair.

Instead, what you want to do is to use your regrets for thinking, because your regrets are signals.

[Regrets] are information. It is the world and yourself trying to tell you something. When we realize that everybody has regrets and that regrets are signals, we can use them to be better … we can use them to make better decisions, to enhance problem-solving skills, [and] to deepen our sense of meaning. (Daniel Pink)

Therefore, the idea of reclaiming regret is not to avoid it but instead to approach it as a force for progress.

How regret boosts performance

Dealing with regrets systematically allows you to improve. They instruct where you need to make a change, and clarify what is important to you.

The challenge is the fact that regrets hurt while they instruct.

If you want the instruction, you have to be willing to sit through the hurt and discomfort of admitting that you can do better in the future.

Regrets revealed

Through Daniel’s research, spanning thousands of people from over 100 countries, he found four core regrets:

Foundation regrets:

“If only I had done the work”. These are the small decisions in life that could have negative consequences later.

Boldness regrets:

“If only I had put myself out there and taken the chance”. These are the regrets that people have about not putting themselves out there, like not studying abroad, avoiding asking your crush out on a date, or not starting your business.

Moral regrets:

“If only I had kept to my principles”. These regrets are those that come from not sticking to your word, falling back on a promise or your moral code, and doing the wrong thing.

 Connection regrets:

“If only I had reached out”. We feel these regrets people when we let a relationship – romantic, platonic, and family – fade.

How to deal with your regrets

  • It is important to treat yourself with kindness when you are handling your regrets
  • Disclose your regret with whoever you feel safe with and close to
  • Draw a lesson from your regret

I think what’s interesting about those moral regrets is that … I find that kind of regret … very heartening because what it suggests [is that] we want to be good. We want to do the right thing. (Daniel Pink)

If we understand what people regret, then we can also understand what people value.

Daniel’s advice to private practitioners

Take one day at a time. Show up, do the best you can for the day ahead of you, and only that. In adversity, think about tomorrow when tomorrow comes and focus your energy on what is in front of you.

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Meet Joe Sanok

A photo of Joe Sanok is displayed. Joe, private practice consultant, offers helpful advice for group practice owners to grow their private practice. His therapist podcast, Practice of the Practice, offers this advice.

Joe Sanok helps counselors to create thriving practices that are the envy of other counselors. He has helped counselors to grow their businesses by 50-500% and is proud of all the private practice owners that are growing their income, influence, and impact on the world. Click here to explore consulting with Joe.

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Podcast Transcription

This is the Practice of the Practice podcast with Joe session number 665.

Well, welcome to the Practice of the Practice podcast. I am Joe Sanok, your host, and we cover so many things here on this podcast that have to do with business, whether it’s marketing, ways to think about new things, regrets we have. Today I am so excited for the guest that we have; with millions of copies of his number one New York Times bestselling big idea books sold, a renowned Ted talk that has been viewed more than 38 million times, lectures around the world, a popular masterclass and the acclaim of everyone from Oprah to Malcolm Gladwell, Daniel Pink has changed the way we live by changing how we think.

With his extensive scientific research and practical takeaways his books have transformed the professional and personal lives of his readers. In his newest book, pink moves from big ideas to big emotions by exploring the transforming power of our most misunderstood yet potentially most valuable emotion regret. Everyone has regrets. They’re a universal and healthy part of being human, but they often have an underserved, bad reputation. In The Power of Regret: How Looking Backward Moves Us Forward, Pink helps us understand how regret works, how they can help us make smarter decisions, perform better at work and school and most important, bring greater meaning to our lives. Daniel Pink, welcome back to the Practice of the Practice podcast.
It is good to be back to you. Thanks for having me.
Yes, well, this book comes out in early February, 2022. So that’s in just a little bit after this airs. So folks are going to run out and buy the book. I want to break up this interview into four main parts. I want to start with talking about the regret reclaimed, that section then moving into regret revealed, then regret remade, and then talking about maybe some of the personal side of both of our lives in regards to regret, in regards to thinking through things. But first, even before we dive into that, I’d love to hear why do you care about regret? Why was that something you decided to spend a whole book working on?
Because I had them and I was trying to reckon with them myself. I found that when I talked about these regrets instead of people recoiling from them, people really leaned in and that’s always a good sign for a writer.
Yes, yes. Kendra Hall, we just had her on Ask the Expert. She’s from Success Magazine. She was talking about how, oftentimes we write the books that we need our most ourselves. So that’s good to hear.
Absolutely, agree with that. I agree with that completely. Writing a book is such a pain that I would never write a book that I would not want to read. In fact, one of my tests seriously is that I would never want to write a book that I would not want to read the first week that it’s out.
I feel like if you’re going to spend the time to put together a book proposal, write the book and then promote the book, I mean, you’re talking about a multi-year process and if not longer. So if you’re going to spend that much time on something it has to be something that you’re really passionate about diving into.
Amen. It takes years to work on it and then you live with it arguably for the rest of your life. So the bar is high.
It is. Well right at the beginning of the book you say embedded in songs, blazed on skin and embraced by sages. The anti-regret philosophy is so self evidently true that it’s more often asserted than argued. Why invite pain when we can avoid it? Why some in rain clouds, when we can bathe in the sunny Ray of positivity. So take us into just how we’ve thought about regret, typically that whole no regrets, like no fear or all of that. What did you learn in that first section? Enlighten us in that area.
Well, I mean, as you say, Joe, we have this, a lot of people have this philosophy of no regrets, that you should never look backward. That you should always think positive that if you’re feeling even a little bit of a pan of regret, you should just bat it away and say no regrets. I’ve talked to, and it’s all over the place. Celebrities talk about this, religious leaders talk about this. People get tattoos that say no regrets. It’s a bad idea. Frankly, it is a pretty ineffective blueprint for living. The reason for that is that everybody has regrets. Every single person has regrets. If you don’t have regrets, it’s a sign that you are a small child whose brain hasn’t developed. It’s a sign that you might have some brain lesions or some neurodegenerative diseases or a sign that you’re a sociopath.

Everybody has regrets. It’s one of the most common emotions we have. The reason it’s one of the most common, is it’s also one of the most useful. That it’s there for a reason. It’s there to clarify. It’s there to instruct. So this no regrets philosophy is a colossally stupid idea that I’m trying to push back on and try to show people that we shouldn’t wallow in regrets. No way. We shouldn’t ruminate on our rights. We shouldn’t let them dominate us, but if we approach them in a smart and systematic way, they can be an incredible force for forward progress.

That’s particularly true on some very, very specific business related things that might be useful to your audience. Leaning into your regrets can make you a better negotiator, leaning into your regrets can make you a better strategist. It can make you a better problem solver. So that’s what I’m trying to do when I talk about reclaiming your regret.
Now is this no regrets, like hashtag I’m so awesome, living me be me, all this Instagram worthy, I’m just living my best life, no regrets. Is it that more of a modern phenomenon or is that something that we’ve seen have threads throughout history?
That’s a very interesting question and I’m not sure. I think that it is more modern than not modern. I think that a force that propelled it to the top was the positive thinking movement in the United States in the mid-20th century. Again, here’s the thing, I’m not against positive emotions at all. I’m absolutely pro positive emotions. We need a lot positive emotions. We should have more positive emotions and negative emotions. All I’m saying is that if you have only positive emotions, if your portfolio has only positivity in it, you’re going to make some mistakes. So we have to be smart and systematic and strategic about how we deal with our emotions.
I think it’s chapter four, you talk about Olympic medalists and, I think it’s called the agony to ecstasy scale. Will you talk about that in bronze medalists compared to silver medalists and regret? I found that so interesting.
This is a very famous study. It’s been replicated many times in other Olympics as well. It’s a study done by Tom Gillich at Cornell Vicki Medic and what they did is they actually looked at the emotional, the facial expressions essentially of Olympic medalists. So what you would expect is that gold medalists are the happiest, silver medalists are the second happiest and bronze medalists are the third happiest. You would only be partly right. Gold medalists are easily the happiest when people evaluate their facial expressions, but actually bronze medalists are routinely over and over again, and once, as I said before, it’s been replicated many times, bronze medalists are routinely happier than silver medalists, which doesn’t make sense. Because they finish behind.

But this has to do with what people, what logicians really call counter factuals. You imagine a world that runs counter to the facts of the current situation. So what happens is that for silver medalists, they say, “Ah, if only I pedaled faster, I’d have won gold,” whereas bronze medalists say, “At least I didn’t finish fourth.” So this is a big part about how we navigate through the world and how we reckon with reality and how we assess both the positivity and negativity of our own lives.
When you think about regret reclaimed what for you in that first section are some of the biggest takeaways, whether it’s the research or the case studies, I love the balance that you have between pulling in research and giving practical application stories behind it. When you say regret reclaimed, like what stands out to you as some of the biggest researcher stories for that section?
The two biggest ideas in there are very simple, number one regret makes us human. Everybody has regrets. We have to normalize that. The problem isn’t that you feel regret. The problem is if you don’t feel any regrets, that’s a warning sign. But what you have to do is you have to use those regrets properly. So again, it’s like, there’s always nuance here. So you can take your regrets and you can say no regrets and ignore them. That is a bad idea. Okay, that leads to the illusion. However, you can take those regrets and you can say, oh my God, I’m the worst person in the world. Oh my God, I’m paralyzed by regrets. Oh my God, these regrets are so massive. I’m going to actually exonerate myself from doing anything. That’s a terrible idea, too.

That leads to despair. What you want to do is you want to use your regrets for thinking. Regrets are signals. They’re information. It’s the world, it’s yourself trying to tell you something. When we realize that everybody has regrets and that regrets are signals, we can use them to be better. We can use them, as you said at the beginning, Joe, to make better decisions. We can use them to enhance our problem-solving skills. We can use them to deepen our sense of meaning. So if we take the idea here of reclamation, of reclaiming is that I want us to not say that regret is this horrible thing that should be avoided all the time, but regret is this complicated thing that if we approach it properly can be a force for progress.
What are a couple ways that it can boost our performance How could you —
Oh, so there’s some really interesting research on particularly in problem solving. If you give people problems to solve in a laboratory setting, and then you report to them how well they’ve done and if you make them regret their poor performance, instead of disillusioning them in many cases, it actually gets them to be more persistent on the next set of problem solvings. If you look up, Adam Linsky and other people have done some very, very good research on negotiation. If you get people to reflect on their regrets of previous negotiations, they end up faring better in subsequent negotiations.

There’s other research showing that regretting just missing getting a prize, a big scientific prize makes people more likely to be successful over the course, the further course of their careers. So there’s this, so again, over and over again, what it shows us is that dealing with regret systematically allows you to improve because as a key, which is so central to this, regrets instruct, regrets clarify. So if we close our ears to that information, we’re not going to get the instruction, but if we actually find the instruction so painful, because it reveals that we made a mistake, that’s going to be bad too.

Here’s the challenge, Joe; regret hurts and regret instructs, but if you want the instruction, you got to get a little of the hurt and you can’t avoid it. But if you deal with it properly it has an array of benefits. There are also some very, very interesting studies out there showing that reflecting our regrets actually deepens our sense of meaning and purpose too.
In what way does it deepen our sense of meaning and purpose?
Well, when we think about sort of missed opportunities, it is a reminder of what actually really matters to us. So there’s somebody in the book who I wrote about who regretted not spending time with her grandparents, in fact, sort of resenting that they lived with her for part of the year. She realized that she missed something big. So she used that sphere of regret to say that’s not going to happen to me with my own parents. So she changed her behavior to her own parents to make sure in this particular case that she was collecting stories from them and understanding their lives.
It makes me think about, I’m a parent of seven and 10 year old girls, a single dad and thinking about, well, how do I apply this as a dad to appropriate allow my kids to have that regret unfold while also not causing undue pain. It’s such a tightrope walk there but even allowing things to unfold, I think in our generation of parents, so often it’s shielding our kids from pain, shielding our kids from regret and making life so easy for them that there isn’t that grit that’s built, that is needed to survive in the world.
I think it’s a really great point and I think that in general, we haven’t done a good enough job, especially in this country of helping people reckon with negative emotions. Negative emotions are part of life and they shouldn’t be ignored and they shouldn’t be walleted in. They should be confronted because when they confront us, they’re often signals. The most common negative emotion that we have is regret.
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So you start out the second part in regret revealed where you talk about in 1949, the Gallup polls and how regret was viewed in 1949, how that changed over time. When you talk about those studies and just how people’s way that they viewed regret in 1949, compared to moving on where at the beginning people were saying there’s not much that I regret and that wasn’t really a thing they were talking about. Talk a little bit about that and how it changed.
So Gallup started investigating this question of what people regret in the 1940s exactly as you say, and they spun their wheels a little bit when they were first doing it because people didn’t really like the question. They weren’t really sure because, I think partly because the United States had just come out of World War II and that was a, in some sense, a struggle for survival and people were actually, and this is also the beginning of the positive thinking movement and people were looking forward understandably and appropriately. However, as time went on pollsters and academics began asking this question again, what do people regret? They kept at some level hitting a wall. They couldn’t come up with a clear answer to that.

I actually tried that myself. I did a poll myself called the American regret project where we surveyed 4,489 Americans and what I found is that people, I was trying to find out what do people regret? I found out they regret a lot of things. They regret things about their family, they regret things about their romantic partners, they regret things about their health and their career and their education. So that was a little bit of a conundrum, but I also did something else, which is I collected 16,000 regrets from people in 105 countries. When I started looking at those, I realized that deep down, over and over again, people do end up regretting the same four things.
I was, I want to have that on my list.
They have very little to do with the domains of our life. That is, we were asking the question in the wrong way. We’re trying to categorize, I did this too, we’re trying to categorize things is this a career regret? Is this a romantic regret? Is this an education regret? What I found is that those surface domains were less important than this hidden architecture that was hidden beneath.
Walk us through those four core regrets. I’d love to hear more about those.
Sure. They’re very interesting and it’s interesting how much they come up over and over and over and over and over and over again around the world. So one of them is what I call foundation regrets. Foundation regrets are if only I’ve done the work. These are regrets that people have about say smoking or about not saving money or about not taking care of their health, small decisions early in life, that accumulate to bad outcomes later in. So that’s one category.

The second category are what I call boldness regrets. Now boldness regrets are a good example of why the domains matter less than what’s going on underneath. So let me give you an example. I got a lot of people in this database, especially Americans who went to college, who said, ”Oh, I really regret not studying abroad. I should have gone over. I should have taken the, I should have done, taken that chance and gone and studied abroad when I was in college.” Then I have literally, Joe hundreds of people around the world who have regrets about not asking out a crush man or woman and not say, oh, there’s this person I really liked and I wanted to ask him or her out and I was too chickened to do it. I mean, it’s unbelievable. Hundreds of those kinds of regrets.

Then I have regrets about people who wanted to start a business, but never pulled the trigger on that. So the first one is an education regret. The second one is a romance regret. The third one is a career regret, but they’re not different. They’re the same. It’s all a regret about not taking the chance. So that’s what boldness regrets are, if only I take the chance.

Moral regrets are if only I’d done the right thing. These are people who make a decision that breaches their own moral code or hurt some, in many cases hurting somebody else, but that violates their own moral code. They had a moment in their life when they could do the right thing or do the wrong thing. They do the wrong thing and they regret it. Then finally, the fourth category, huge category are connection regrets. These are regrets about relationships that come apart, usually in slow, dramatic ways and people want to reach out and they don’t, and it drifts further apart. These relationships, some of them are romantic relationships, but a lot of them are relationships between parents and kids, between siblings, between other relatives, between friends. So connection regrets are if only I’d reached out and these four regrets come up over and over and over again, and they tell us something I think very revealing about the human condition.
It’s interesting that worldwide and over thousands and thousands of regrets, people submitted that most of them fall into these four categories. I like that you pull them away from domains, but just almost like postures towards life. I mean, I can think about in my own life, either times that I’ve stepped into those things and don’t have regrets around it or have stepped away from those things and have regrets about it. So to frame it out that way, I think it feels very new, but it feels very grounding, like how humans are experiencing regrets.
Yes. I think so. I mean, I think that, I sort of fell into that trap initially and that I was looking at the domains of people’s lives because that’s how we always looked at it and I hit the frustration where it’s like, wait a second. I’m not getting anything interesting here. It’s like people are reporting regrets across everything. Then, so it’s at some level not to get in the weeds here, but it’s the difference between quantitative research and qualitative research, qualitative research, where you can go in and you and read as I did insanely 16,000 regrets that you begin to hear the sound of what’s really going on in a way where if you just have people express their regret and putting them into preexisting categories, you sometimes don’t.
Well, I love how you say at the end of the boldness chapter where you say the lesson is plain, speak up, ask them out, take that trip, start that business, step off the train. I would love to know knowing those four regrets, how does that shift how you personally enter into life or the people you care about, how do you share with them or just, how did that shift things for you knowing that most people have these four regrets? Then lead us into that anticipated regret thing that you talk about?
I think it was interesting, I did see myself in a lot of these regrets. So for instance I had have regrets in all of those categories and it made me, in a sense, it sort of normalized those for me. It made me think, okay, I’m not some weirdos who has these outlandish regrets that make me an aberration, but it’s I’m like everybody. I have these regrets that I think are integral to the human condition. I think the biggest one for me, the most powerful one for me were the connection regrets. Because I found myself falling into the trap there. So with these connection regrets, what you have is you have, as I mentioned, these relationships that were intact or should have been intact and people don’t want to reach out.

And the reason they don’t want to reach out is that they think it’s going to be awkward and they think the other side’s not going to care and they’re wrong. The others, it’s much less awkward than people think. The other side almost always cares. So that really changed my view of this. My own personal philosophy has changed on this and I’m at a juncture where I’m wondering, should I reach out or should I should I not reach out? I’ve answered the question by being at that juncture you always reach out.
So when people reach out, you’re saying that statistically, it usually works out fine if that person wants them to connect with them. That worry is actually the thing that’s fueling that separation more than other things?
Exactly. Well, what we do is we overestimate how awkward things are going to feel. We also underestimate, in some ways how much other people are like us. So the people who I interviewed in the book who were resistant, it was like, oh, I don’t want to reach out to that person because I haven’t talked to her for 20 years and she’s going to think it’s creepy and weird if I reached out. Then I say, well, how would you feel if she reached out to you? They said, oh my God, I would love it. That would be great. I would be so touched. I’m like, well you’re not that special.
Are there stories like that that really stand out to you from the book that maybe impacted you more than others that you cited in the book?
Oh, there’s so many so many stories in this book. There is a guy who regretted not getting off the train with woman he met in Europe 40 years ago and it still bugs him. There is a 71-year-old woman in New Jersey who is still bothered by stealing candy from a store while she was a little kid. There is a woman who had a friend who was dying of cancer and meant to reach out and meant to reach out and meant to reach out and by the time she actually had reached out, her friend had died that morning. But then she used that regret to recalibrate her relationship with other friends and how she dealt with other friends. There is a a lot of friendships that came apart and people were skitish about reaching out and some did and some didn’t. So it’s —
How important is it to do something about those regrets? So I’m thinking about the lady that stole candy. How important is for her to figure out how much that costs, maybe account for inflation, then give them 20 bucks versus just let that stuff go?
So on some of them, I think you’re right about that. I think you’re right about that. I think it’s, on that one is that I don’t think that person had fully reckoned with that. That’s a big part of the book. The big part of the book is like, what do you do with that thing? So in that situation, you have to ask yourself, you have to sort of reframe how you think about it and how you think about the world. How you think about yourself and how you think about that regret. So there’s some interesting research on self-compassion, which is you treat yourself with the same kindness that you would treat somebody else. It’s powerful research.

So in that case for this particular woman, with this stealing regret, I would say, okay, so if a friend came to you with this regret, would you treat them with contempt or with kindness? You probably would treat them with kindness. Do you think that you’re the only person with this regret? Or is it part of the human condition? Believe me, you’re not the only person with this regret? Then I think there’s something to be said, and I know there’s something to be said for the act of disclosing it and then drawing a lesson from it. So maybe you say, well, I don’t want to do those kinds of immoral things again.

So you use that as a lesson, you transmit it to other people and tell them how bothered you’ve been by this for so long. I think in her case, I think it’s that she never fully reckoned with it that. And I think at some level she wanted to say no regrets, da, da, da, but she couldn’t because she still felt bad about that. I think what’s interesting, Joe, about those moral regrets, at least to me, is that I find that regret, those moral regrets, very heartening because what it suggests is that we want to be good. We want to do the right thing. Somebody who’s bugged by something, an immoral act of 60 years ago, that’s somebody who wants to be good and her brain and her soul is telling her it’s important to be good.
So has this given you some hope for humankind?
It’s interesting, that’s a very, very interesting question. I think so. You wouldn’t expect it because the, somebody asked me the other day, it’s like, okay, so you read through all these regrets. Was that a downer? I’m like, well, actually it’s a good question, but it’s weird. It wasn’t a downer. In fact, it was inspiring in a way, because I think that these four regrets reveal what makes life worth living. I think these four regrets operate as a photographic, negative of the good life. If we understand what people regret the most, we understand what they value the most.

So people in their regrets are telling us what do they value? What makes life worth living? I think these four regrets tell us, foundational regrets, we value stability and you can’t have a good life if it’s uncertain and precarious. Boldness regrets, I think most of us want to do something. We don’t just want to like hone it in all day. We want to lead psychologically rich lives. More regrets, as I said, I think most of us want to be good. And connection regrets. What do we need? Love. So this is a surprise to me, Joe, is that I took on this topic and it sort of led me to this insight on what I think people find meaningful in life.
It’s like you started with wanting to deal with your own regrets and just let go of those things or helping people do that, but then define this deeply rich human, like who are we at our core being revealed through these regrets? I mean, what a beautiful thing, what a beautiful insight?
Well, and lucky, because again, it’s serendipitous, at least because it wasn’t something that I was going after. It wasn’t something I was trying to find. It’s something that at some level found me.
I love that about writing a book where there’s things that just reveal themselves in that process that it wasn’t in the book proposal. It wasn’t what you thought about it all, but it just kind and unfolds. Talk a little bit about anticipated regret. You, in the book talk about that. You talk about that in comparison with the COVID vaccine and with different ways that people anticipate regret. I want to read a quote from that section that I’m going to pull up right here, where you call it the regret optimization framework, “This revised framework is built on four principles. In many circumstances, anticipating our regrets can lead to healthier behavior, smarter professional choices and greater happiness, yet when we anticipate our regrets, we frequently overestimate them buying emotional insurance we don’t need, and thereby distorting our decisions. And if we go too far, if we maximize on regret minimization, we’ll make our situation even worse. At the same time, people around the world consistently express the same four core regrets. These regrets endure. They reveal fundamental human needs. Talk a little bit about that regret optimization framework.
So when we anticipate our regrets, what we’re doing obviously is we’re basing our current behavior on our predictions about what we’re going to regret in the future. Now that’s often very useful, but it’s not perfect as that optimization thing makes sense. So I’ll give you one of my favorite examples of this, is taking multiple choice tests. When I was a kid, the advice was always, if you think the answer is C and then you come back and say, oh, maybe it’s A, always stick with your first instinct. Never change your answer because your first instinct is right. That is terrible advice.

There’s research, showing that actually, when you change your answer, you’re more likely to get the correct answer. But the problem, this, what stands in the way of people is anticipated regret, because if they anticipate going from the right answer to the wrong answer, and that is so painful, and it’s way more painful than simply sticking with the wrong answer, because they’ve taken that action. So people end up making suboptimal choices because they overstate how much regret they’re going to experience. What’s more is that we can’t use anticipated regret for everything. We’ll go nuts. So you can’t say, oh, in five years, am I going to regret buying a blue car or a green car? It doesn’t matter. Trust me, it’s not going to matter at all.

A lot of these decisions don’t matter. Should I have my gutters cleaned on a Tuesday or a Wednesday? It doesn’t matter. So many of these things don’t matter, and there is some fascinating research, it’s in some ways like incredibly important part of social psychology, writ large on the difference between maximizers and satisfiers. Maximizers try to get the best out of every single decision, satisfiers say that some decisions were good enough is good enough and what the research tells us very clearly is that maximizers are miserable. If you maximize everything, you’re going to be miserable.

So what you have to do is you have to use your anticipated regrets to maximize what we know matters and what we know matters comes from what we were just talking about, building your foundation, taking a smart chance, doing the right thing and building connections and affinities with others. That’s what matters. Those are the regrets that you should anticipate and those are the decisions that you should maximize. Everything else, the color car you’re going to buy, what you’re going to have for dinner, which sweater you’re going to wear, it doesn’t matter. So I just want, so I want people to use, anticipate a regret is very useful in many ways, but it can sometimes lead us to bad decisions and sometimes paralyze us. So the way to use it is to anticipate regrets for the things that matter most and the 16,000 people around the world have told us, we know what matters most.
It reminds me of, I was in a counseling session with my therapist and he and I were talking about my relationship with my parents. I was saying I feel like I should spend more time with them, but I really only want to see them maybe once a week. They live in town. And he talked about how, he’s like, you’re anticipating regret and pain by creating your own regret and pain right now in the moment in your anticipation. He’s like, if right now, what feels good to you feels connecting to you is once a week, do once a week.

If later on you want to change that ,it is just, I think so much of our lives, we think, well, when my parents die, I’m going to want one more day with them. Of course, whether I spend five days a week with them, or one day a week with them, when your parents die, it’s painful. So to be able to then say for right now what is it that I feel good with and allow that to unfold, for me was one of the more healthier counseling sessions where you really pushed me to just let that stuff go.
I think that’s right. We have to, again, this is the idea of maximization versus satisfaction. There’s certain things that we want to satisfy on. I think that’s good advice from that therapist.
Well, I want to get into that part four. I would love to hear for you personally, what’s something that you regretted and that maybe through this work, through this writing, through learning these frameworks, you personally applied to maybe let go or reframe that regret.
Well, I mean, I have a lot of regrets. One of my biggest regrets is when I was, especially when I was younger, is that I felt I wasn’t especially kind person. I wasn’t somebody, I have all kinds of regrets from people who bullied other kids and people really bugged by that. I don’t have that regret, but I have almost like kindness by in action regrets, a lot of them, because with the time that I was a kid, or even the times that I was a young adult, you know I would be in situations where there were people who were clearly being left out, people who were on the periphery, people who weren’t being included. I’m a writer. I’m an observer. I knew that. I saw that happening and I didn’t do a thing and it really bugs me today.

That sphere of negativity, I could say, “Oh, no regrets. It doesn’t matter.” Or I could say, “Oh my God, I’m the worst person in the world. I’m going to spin myself into oblivion.” Or I can say, “Wait a second, this regret is telling me something. What is it telling me and how does it point a path forward?” So, because of that regret, I have tried maybe not always successfully to be more compassionate, understanding and kind in my dealings today, especially with regard to people who are on the periphery and not being brought in, trying to make an affirmative effort to draw them in, because I felt so bad about not doing that earlier in my life.
That’s so awesome to hear how you apply that. The last part I want to ask about is totally selfish. As a writer, I want to know, how do you get stories? How do you find research? What’s your process as a writer in gathering stories? I know some writers are just, whenever they see something, they put it in a file. They don’t know where they’re going to use it. Other people say, here’s the theme I’m looking for and they go after it. From a process standpoint, how do you find such amazing stories and research?
Well, thank you for that. So I’m a big believer and generating as many possibilities as possible. So if I see an idea that I find intriguing, if I see a story that I find intriguing, especially at the early stages, Joe, I don’t scrutinize it a lot. I say, oh, that’s interesting. So I have various ways of capturing those tools, capturing those things. I use a lot of paper notebooks. I have a file in my computer that I call spark file, which is just simply shards of things that I put in there. I have a file of ideas and stories on my email. I have a folder for ideas and stories on my Dropbox. I just dump stuff.

Again, to me, the two most important steps are generate as much as possible. The only way to have a good idea is to have a lot of ideas. The only way to find a good story is to collect a lot of stories. I’m convinced of that, that quantity is the pathway to quality. I will die on that hill arguing that. So you generate, you capture, but then for me, what you have to do is you have to actually socialize these ideas. So you have to talk about them with people. Nobody’s going to steal your idea. It’s too hard. And I really am interested in seeing how people respond. Do they agree with me? Do they not agree with me? Do their eyes light up, do they lean in, do they recoil?

So that’s one way that I do that. Now in this particular case I was very fortunate because I put up this survey, the world regret survey, where I just invited people to contribute their regrets and we got 16,000 regrets in there. A third of the people were, about 30% of the people were willing to include their email address if they wanted to be contacted for a follow up interview. So that’s how I got those. So the stories in the book are if you think about, let’s say we had 16,000 people, let’s say we had 15,000 people and a third opt-in for emails, that’s 5,000 people raising their hands to volunteer. If I can’t get 30 good stories out of 5,000, I should be in another line of work.
How many interviews of those several thousand did you do with individuals to then get through —
I only did a few hundred. I only did a few hundred with people. And because most of the interviews, I think all of the interviews, most of the interviews, the lion share of the interviews were done during the COVID era, I had to do most of them on Zoom, which is a plus and a minus, depending on … but I only ended up talking to a couple hundred of these people. So it’s sort of a funnel, you got 16,000, and then some people don’t want to volunteer to be contacted and some people do volunteer to be contacted. Then I contact some of them and sometimes the stories are really compelling and sometimes they’re less compelling or sometimes I already have something like that? So that’s just how it works. But again there are, I mean, volume man.
Yes. When you have hundreds of people to interview, are you doing 10 minutes and then you’re thinking if this ends up being an hour, I’ll drill in and reschedule, or what’s the actual logistical structure for those interviews?
It’s a great question. It depends. I want to be polite, but sometimes I know within a few minutes, okay, this is a total dog. So that’s going to, not the person, but just the story. So that’s going to be 15 minutes. Then I try to, on a lot of the ones, I think almost all the ones that were in the book, I have to go back and look, but many, many of the ones that made it into the book, it ended being multiple interviews because they told me their story, the story is really compelling and then as I started rendering the story, I realized I had more questions about it. I wanted to know what happened here, what happened there, what they thought about this. Then the other thing was sort of interesting, which showed you how powerful regret is as a force, is that for several of the people in the book, they would tell me they regret and I would write their story. Then they would contact me in like three weeks saying I decided to do something about it and I’m like, oh, come on, you’re changing the story on me. You can’t do that.
The actual process of sharing their story with you caused some social change. Wow.
Yes. I mean, in multiple, multiple cases. And to me, while that’s annoying as a writer, it’s heartening to me as a human being, because what it suggests is how powerful regret is and how catalytic it can be if we treat it right.
Oh, so awesome. Well, Daniel, the last question I always ask is if every private practitioner in the world were listening right now, what would you want them to know?
I think that I would, I’ll tell you, can I use a story? I don’t know if any of your —
Say whatever you want.
Okay. So here’s what I’m going to do. I’m going to revert to type as a middle aged white guy and use a sports metaphor here. The reason I’m going to use this is because it’s written, literally, as I’m talking to you on a whiteboard right there. In 2019, the Washington nationals, I’m a baseball fan, I live in Washington, DC, the Washington nationals, we were having a terrible season. They’re supposed to have a good season. They’re having a terrible season. It’s May, 1st third of the season they are doing terribly. How are they going to rebuild the season? How are they going to overcome this adversity? Their manager, David Martinez said, here’s what we’re going to do. We’re going to go one and o a day.

We’re not going to figure out the whole season. We’re not going to worry about everything that’s coming up later on. We’re going to go one and o today. I actually think that for so many things in life showing up, going one oh and o a day, showing up the next day, going one and o that day is really the key. I have that written on, on my whiteboard right there. It says, go one and oh a day to help me just do the work today, show up, do the work today, even in the face of adversity. If you do that routinely, it’s going to accumulate to your advantage.
I love it. I love it so much. Daniel Pink, where can people get The Power of Regret? What else should they know in regards to the book?
Well, you can get the book wherever books are sold, online or offline. You can also find out more on my website, which is
Oh, thank you so much, Daniel Pink for being on the Practice of the Practice podcast.
Joe, always a pleasure. Thanks for having me.
Well, go get that book. Think through regrets. I love that idea of foundation boldness, moral and connection, even thinking as a dad, how do I help my kids enter into the regrets that they have and to think through what do they want to work early on? Where do they want to be bold? How do they do the right thing and how do they maintain those connections and when they don’t, how do they recover from that? I can’t wait to just figure that out as a dad, as a business owner, as a friend, and just thinking through my own regrets, thinking through my own things that maybe I wish I would’ve done a little bit differently, having some of that gentleness and saying, yes, I can make changes now, moving forward. I can not go in either of those extremes that Dan talked about to really be able to move forward and to harness that power of regret.

Also today we could not do this show without our friends at Noble, our friends at Noble believe in using technology to enhance, not replace human connection. With noble, your clients will gain access to between session support through their automated, therapist-created roadmaps. To me that’s so important that therapists are helping create these roadmaps, assessments to track progress and in-app messaging. You can learn more and join for free over at Again, that’s

We have some amazing, shows coming up here in the future. In the next episode, we have a discussion about the Faith in Practice conference with Whitney Owens. Then we’re going to be talking about how to structure a sprint week. Then we have the business brothers, Kyle and Eli who are co-founders that try to make a difference in the world together. We are doing four episodes a week now. Can’t wait to have you hang out with us more. Thank you for letting us into your ears and into your brain. Have a great day. We’ll talk to you soon.

Special thanks to the band Silence is Sexy for your intro music. We really like it. This podcast is designed to provide accurate and authoritative information in regard to the subject matter covered. This is given with the understanding that neither the host, the publisher, or the guests are rendering legal, accounting, clinical, or other professional information. If you want a professional, you should find one.