The Power of Regret: A Conversation With Daniel H. Pink

Geoff Mitelman: So we’ll start with your book here, about the power of regret. That regret is an emotion that we tend to think of as negative and we try to avoid, often like pain or sadness. And yet one thing that you talk about is: Regret is universally human. Trying to avoid regret is both a fool’s errand, and in the same way, when we try to avoid pain or sadness, we’re avoiding part of the human condition. So I’d love for you to talk about: What is the value of regret? How do you find this value, and the power of being able to look backward, and why regret actually can have some tremendous value for us here?

Daniel H. Pink: Yeah, yeah. There are 50, 60 years of research on this that tells us very clearly two important things. One, as you say, Geoff – regret is universal. It is ubiquitous. Everybody has regrets. The only people who don’t have regrets are five-year-olds, because their brains haven’t developed sufficiently; people with certain kinds of neurodegenerative disorders; and sociopaths. The rest of us have regret. It’s one of the most common emotions that human beings experience. It’s arguably the most common negative emotion that human beings experience. So it is ubiquitous. But, as you also say, it’s unpleasant, it’s uncomfortable, we don’t enjoy it. I don’t like experiencing regret. And so you have to ask yourself, why is something that is so aversive, so universal, so ubiquitous? And the answer is simple: because it’s useful! If we deal with it right. And there’s a pile of evidence showing that if we treat our regrets properly – that is, we don’t ignore them, we don’t wallow in them – they can help us become better negotiators, help us avoid certain kinds of cognitive biases, help us become better problem solvers, help us become better strategists, better parents, seek more meaning in life. And so, in a way, what I’m trying to do is reclaim and reframe this emotion, because it’s actually transformative – if we deal with it right.

Geoff Mitelman: Yeah. And you talk a lot about this. That’s part of the trick of how do you handle it well, and how do you use it so that it’s not a negative and you don’t ruminate on it, but helps you to not ignore it – but to be able to own it. And one thing that you draw, the distinction between regret and disappointment. And I think that’s a really subtle distinction. Can you expand on that a little bit? Because I think that’s a really key –



Daniel H. Pink: No, it’s an important distinction. And the distinction, really, is agency. Regret is your fault. Disappointment is not your fault. And so a good example of that would be – it happens to be a sunny day here in Washington, DC, where I am right now, but it’s freezing cold right now on the day that you and I are talking. It is so cold – the real feel, the wind chill, is like 20 degrees Fahrenheit. So I wanted to go out for a walk. I actually tried to go out for a walk a little earlier. So I’m disappointed that it’s so cold, but I can’t regret that because I didn’t choose the weather. Now I can regret if I knew what the temperature was and I went outside without gloves on, and my fingers froze. All right, that’s my fault. And so it’s a long-winded way of saying regret is something we have agency over, we have control over. Disappointment is not.

Geoff Mitelman: I think that the agency – that’s really interesting. When we think about religious questions and the mistakes that we make. And you talk about different forms of regret, and we’ll talk about that in a second. But when we think about Rosh Hashanah and Yom Kippur, which are – at least we’re recording this in end of March, so it’s six months away. But when we think about the mistakes that we made and we think about what we did, we think about the sins and the mistakes that we made that we [had] done, and we also regret the things that we didn’t do. And that’s also hard to be able to say, “If only I had done this or if only I hadn’t done that.” And trying to say, “What is my locus of control?” which can be very powerful and also eat us up a little bit here.



Daniel H. Pink: But it’s a great point, because that’s an important question to figure out, because at some level, that is the central question of life, which is: What do we have control over and hat do we not have control over? What is within our grasp, what is within our control, what is the product of circumstance? And so this, to me, is one of the really gorgeous things about this emotion of regret, is that it leads us into these kinds of conversations about the fundamental aspects of the human condition and of a life well-lived.

Geoff Mitelman: Recognizing that life is finite. I mean, I think that’s one of those things about if we lived forever, then there would be no regrets, because then you could redo something.

Daniel H. Pink: Exactly.

Geoff Mitelman: The first Rosh Hashanah sermon I ever gave was actually – it was an editorial cartoon, and it was two people walking down a corner – one coming down one side, and one was the other, and one was saying, “Rejoice. Today is the first day of your life.” And the other was “repent. Today may be your last day.” And it was called”the philosophical showdown. And what I love is that both of those things are always true.

Daniel H. Pink: Right.

Geoff Mitelman: You never know – will you have another opportunity to look back?

Daniel H. Pink: Exactly.



Geoff Mitelman: You probably do have another chance to be able to try to make amends, or make a different decision, or go in a different direction.



Daniel H. Pink: Again, it’s one of those paradoxes. And what’s interesting about that is that if you go and start excavating regret –what it is, what people regret, how they regret, why they regret – a lot of it comes exactly at that collision between opportunities.

Geoff Mitelman: Right.

Daniel H. Pink: Regret is, in many ways, about opportunity. We feel a sense of regret when an opportunity is thwarted or when we blow an opportunity. We feel a sense of hope when we feel like we’re able to act on our opportunities.

Geoff Mitelman: And all of these counterfactuals of being able to say, “if things had gone differently, what might have happened,” in this way.

Daniel H. Pink: Right.

Geoff Mitelman: And you just mentioned excavating the different elements of regret – that originally, when people were talking about regret, it was on questions of education or different questions of marriage. But you actually looked at a slightly different way of thinking about these questions. As if I’m remembering it correctly, it was foundational regret, it was boldness regret, moral regret and connection regret. Can you share – what are those different forms of regret?

Daniel H. Pink: So, traditionally, when scholars, and even some research that I did, looked at “What do people regret exactly?” As they say, they look at the domains of people’s lives, so “this is a career regret.” “This is a health regret.” “This is a finance regret.” “This is an education regret.” And what I found is that that was less revealing than you would think, and that what was more revealing was to find out what was going on beneath the surface. And I was able to get to that inadvertently. I wasn’t necessarily looking for that. I set up something called the World Regret Survey, which, with very little promotion – I mean, two tweets and a newsletter mention – we ended up with 15,000 regrets from over 100 countries. We’re now over 20,000 regrets from 109 countries.



Geoff Mitelman: Wow.

Daniel H. Pink: And it’s an incredible trove and database. And when you read through those, and I read through at least the first 15,000 – I read through the first 15,000 trying to make sense of them. What I found is that around the world, people had the same four core regrets. One of them was, as you say, foundation regrets. That’s “if only I’d done the work.” These are people who regret not saving money, spending too much money, not taking care of their health, not working hard enough in school, smoking, those kinds of things – so small, bad decisions early that accumulate to terrible consequences later.

Second one, which I think goes directly to your point about life being finite and about our either conscious or unconscious knowledge that we are immortal –  our boldness, regrets. Boldness regrets are “If only I’d taken the chance.” And again, it spans the domains of life. So these are regrets about not traveling, regrets about not speaking up, regrets about not asking somebody out on a date, regrets about not starting a business. So that’s boldness regrets.

Third one: moral regrets. “If only I’d done the right thing.” Small category, pretty wide ranging. The two most common moral regrets are bullying and marital infidelity.

And then finally, last but not least, are connection regrets. That’s “if only I’d reached out.” And these are regrets about relationships that were intact or should have been intact, that come apart, and somebody wants to reach out, but they say, “oh, it’s going to be awkward, they’re not going to care,” so they don’t reach out. And the drift continues. I think what’s really, to me, what was surprising was how universal these four regrets were – that over and over again around the world, this is what people were regretting.

Geoff Mitelman: Mhm. And what’s interesting is that a lot of these regrets, and all these regrets, actually, they’re kind of muzzy. And they’re “if only these things had gone differently.” And it’s a lot of what happens – from the study, I know, of cognitive science – of when we think of something very specific, we can envision it very clearly, but a lot of the regrets would have been perfect if only other things had happened. And in fact, it may not have worked out the way that we wanted to. In our brains, it was great. But in reality, is that actually what would have happened?



Daniel H. Pink: Yes and no. I mean, it’s an interesting question, because I found that people were actually somewhat less outcome-ist than I expected. So let me tell you what I mean by that. So let’s take the boldness regrets. The people who – like, I have a lot of people who regret not asking somebody out on a date. And when you interview them or even sort of read their regret more fully, or even – I interviewed several hundred of these people, too. Let’s say that I really regret not asking Bob out on a date 25 years ago. The people who say that don’t say, “Oh, my God, because then my life would be perfect, because I’d be married to Bob, and Bob and I would be living in this beautiful house with these beautiful kids and a two-car garage.” They don’t say that. They don’t say that. What they regret is not stepping up at that moment. They don’t necessarily have wild visions of how perfect things would have been.

Geoff Mitelman: Right.

Daniel H. Pink: So, for instance, I have plenty of people – let’s think about starting a business. When people say, “If only I’d started a business, rather than stay in the lackluster job,” usually again, once again, they often don’t conjure images of, “Oh, I’m going to be the next Elon Musk. I’m going to have riches beyond compare.” It’s really a matter of that moment where they’re at this kind of decision point where you can play it safe or take the chance. And when they don’t take the chance, they regret it – occasionally, because they think that the outcome would be amazing, but mostly because of the decision itself.

Geoff Mitelman: Yeah. Of the process of that decision or that lack of that decision, right. It’s not so much of, “Here’s exactly how my life would have been,” but the regret is that “I didn’t take that chance” or “I had acted in this way or hadn’t acted in this way.”

Daniel H. Pink: And I think this goes to one of the points you made earlier about life being finite and about mortality, because I think that’s really the case with a lot of these boldness regrets – which is that at some level, consciously or not, we have this sense that – we have this knowledge, not even a sense we know in a way that other species do not, that we’re all going to die. And I think that that can be a kind of a backbeat. It’s not necessarily the melody of our lives, but at some level, it can be the backbeat of our lives. And so a lot of us say, “Well, I had a chance to do this, and I blew it, and I’m not here forever. When am I going to step up and do something?”



Geoff Mitelman: Mhm. Well, and you mentioned a couple of minutes ago that one of the things about regret is how it’s used effectively, right? It could be something that could lead to anxiety and depression if you ruminate on it for too long, and yet can also be an incredibly powerful tool.

Daniel H. Pink: Absolutely.



Geoff Mitelman: So, what are the ways in which it can be valuable? What are the ways in which it can be – not transformed, but it’s almost like the rabbis talk about that there’s sort of the seed of the negativity that can actually flower into something that’s wonderful.

Daniel H. Pink: Yeah. So, at one level, what it shows – let’s take something like negotiation. And we can talk about the specific ways to do this in a moment if you want, but let’s talk about something like negotiation. There’s a lot of research in negotiation, and one reason there’s a lot of research in negotiation is that a lot of the negotiation research uses a common fact pattern that they can then put in different situations so they can say what happens, how do people negotiate, if we give them a little time? A lot of time? Three people, four people? We prime them.

So you can take this common fact pattern and play around with it. And so the negotiation research shows pretty clearly this, that if you’re in a negotiation – you do a negotiation – and then following the negotiation, you actually think, “What do I regret from that previous negotiation?” You actually invite this aversive feeling. You don’t try to bat it away. You don’t pretend it doesn’t exist – you invite it. “I want to think about my regrets” – people who do that are better negotiators the next time around.

And you see that same kind of thing with problem solving, you see the same kind of thing with certain kinds of strategy thinking, strategic thinking. And what it tells us is, I think, at a broad level, and we can talk, again, mechanistically, how to do this is that we haven’t been taught – especially in secular society, we haven’t been taught well, to deal with negative emotions. And so what happens is that, especially here in America, we are kind of intoxicated on positive thinking. And so we think we’re supposed to be positive all the time, that when we’re not positive, there’s something wrong with us, that we’re doing it wrong. So when we feel a spear of negative emotion, which we all do because we’re human beings, one tendency is to put our fingers in our ears, and start going, “blah, blah, blah, blah, blah,” and try to drown it out. Bad idea – that leads to delusion.

Now, the other thing that happens, I think, all too often, is that because we’re not equipped to deal with these negative emotions, they can start spiraling – they can start gathering force. They can lead to, as you put it, some rumination. That’s bad, too.

So, what we shouldn’t be doing – there’s a kind of a meta question out here of “What are negative feelings for?” Some of us say “negative feelings are for ignoring.” Others of us are like, “negative feelings are for wallowing. Negative feelings are the truth itself.” The way I look at it, feelings are for thinking. Negative feelings, especially, are for thinking. They are signals, they are data. And if we go down the middle – not ignoring them, not ruminating on them, but simply saying, “Hey, what’s this telling me?” Then there’s a pile of evidence that this negative emotion in particular is transformative, or at least can be transformative.

Geoff Mitelman: It’s almost like Daniel Kahneman’s work, of Thinking Fast and Slow, being able to – your immediate reaction of these kinds of things that we regret. Often, I would think that a lot of the things we regret are that the quick emotional reaction, as opposed to being slow and deliberative and being able to say, “that may be the right decision, what this quick, immediate emotional reaction is. But let me pause and reflect on this and be able to say…” I think of a lot of businesses of doing a pre-mortem, of trying to say, like, yeah, “everything has gone to hell, let’s figure out why.”

Daniel H. Pink: Well, that’s a great. Pre-mortems are a great way to anticipate future regrets, definitely.

Geoff Mitelman: Yeah. And now you started to mention that particularly western and secular society ignores negative emotion. There tends to be a kind of toxic positivity, of “everything is wonderful.” But we can talk a little bit, because you mentioned right beforehand about how religion can actually help us deal with regret. And I think some of that is all religion – and particularly, I’m thinking about Judaism and Christianity, but also Buddhism, of “there’s suffering, there are mistakes, there are ways we screw up, and there are opportunities to be able to make amends here.” So where does religion come in, in your mind?

Daniel H. Pink: Well, but I think that what religion does is that it offers people a set of tools, a set of processes, a set of methods, for dealing with these negative emotions, rather than leaving people adrift.

Now, there’s a lot of evidence showing that the community aspect of religion is incredibly important. The reason that people of faith, regardless of the faith, tend to be healthier physically and mentally. I think a big part of that is that they have people, first of all, they often have a sense of purpose in their life. And second, they often have a community that they’re part of, that takes care of them and that they take care of, and that itself is inherently fulfilling.

But I think in this case, what religion does – and that could be part of it – I think, in this case, what religion does is it gives people tools, processes, systems, methods – call it whatever you will – a way to deal with it. And so if you look at, say, Catholicism: confession, repentance, right – the world regret survey was in some ways an online confessional. People had a mechanism, a process, by which they could disgorge their regrets.

If you look at Judaism, the day of atonement, there’s a day set aside, carved out in the calendar, where you reflect and think about your regrets, and you vow to do better next time. And even things that are at the edge of religiosity – things like Alcoholics Anonymous – it, too, has a process that is about divulging and about making amends. I think that in general, though, we have left people without the, again, I don’t know the right word here, Jeff, but I keep – steps, process, tools, methods, techniques or whatever for dealing with negative emotions. And so, religious traditions and even kind of quasi-faith traditions like AA give people the tools to deal with that. But in the rest of secular society, we’re so over-indexed on positivity that when people feel negative emotion, they think there’s something wrong with them. And so they either go into this blithe form of denial or they get completely brought down by it, when, in fact, what we should be doing is thinking about it, applying a process to it.

Geoff Mitelman: You know, thinking about Rosh Hashanah and Yom Kippur and the day of atonement, that what’s so helpful – there are a couple of elements of this. It’s not only a ritual there, and everybody is in that mindset. Everyone surrounding you is thinking about that, at least ideally. But first of all, all the list of the sins and the ways in which we regret from this past year – first of all, they’re all in the first-person plural, so nobody says, “okay, if you were angry, raise your hand. If you were unfaithful, raise your hand.” They read the words, and they can see whichever one speaks to them at that moment. But it allows that level of anonymity.

Daniel H. Pink: Yeah, it’s a good point.

Geoff Mitelman: It also lists all sorts of different ways in which we, at least in Judaism, the phrase is “missed the mark,” that we might not have thought of otherwise. In the same way that when people say, what are you grateful for? Everyone’s going to say, “my friends, my family, and my health.” And they’ll just sort of say it in a rote kind of way. But being able to say, “these are some things to be able to think about that you may have regretted in this past year,” I think that’s incredibly valuable to have that set of words that you can rely on, instead of having to think of it yourself.

Daniel H. Pink: It’s a really great point and one that I haven’t actually. I’m making a connection now that I hadn’t made before, because when I’ve been out talking about these four core regrets, what I found is that people begin locating themselves in those things. So they say, “Oh, yeah, you know what? It turns out I do have a connection. I didn’t think of it at first, but now that I have a way to categorize, now that I have the vocabulary to describe this, oh, I know what you’re talking about.”



Geoff Mitelman: Yeah. I think that’s one of the things that’s so helpful, of being able to articulate these kinds of questions.

Daniel H. Pink: It’s also destigmatizing. So if you look at, say, like, to use your Yom Kippur example, if you sort of have this way, you affirm, “I was not truthful.” And you realize, well, you’re definitely not the only one. And I had that experience at an individual level myself and having my own regrets, and thinking, initially, that they were somehow singular and idiosyncratic, when in fact they’re completely commonplace and typical.

Geoff Mitelman: And what’s interesting is, I would think that there were quite a few from the world regret survey that were either almost surprising of how open they were – although some of that, I’m assuming, was [because] there was a level of anonymity.



Daniel H. Pink: There was. I gave people anonymity. But we’ll come back to that in a moment.

Geoff Mitelman: But I think that it’s so hard to be able to destigmatize some of these questions, because some of them, if somebody said, like – “yes, I committed murder,” that’s – okay, that’s something to be able to. There may be some other steps there.

Daniel H. Pink: A lot of people confess to sins. I don’t think there was anybody who confessed to a crime.

Geoff Mitelman: Right.

Daniel H. Pink: There’s a distinction there.



Geoff Mitelman: Right. I think what’s interesting, though, is when people say they“commit” something, that’s usually “commit a sin” or “commit a crime,” they’re linked in people’s minds here. But I’m curious as to things that may have surprised you from the World Regret Survey, if there were ones that, whether that was the regrets that came out or the process by which you discovered all of these.



Daniel H. Pink: Well, I guess there were two things. One of them was, going to, what we were just talking about a moment ago, was how forthcoming people were. I think it was partly because of the veil of anonymity, but there were many people willing to pierce the veil of anonymity. So let me give you an example. In the survey, I said, invited people to submit one of their big regrets. It’s totally anonymous – I asked them, though, for location where they live. I asked them for age and for gender identity, but that’s it. But then I also said, “If you’re interested in being contacted for a follow up interview, please leave your email,” Thinking that we’d get maybe five or six people who would opt in to do that. We got about 30 something percent of people opted in to be to talk more about it. So, to me, that itself is inherently surprising and quite fascinating and revealing.

So we’ve now got 20,000 people around the world who say, “Yes, I want to share a regret with a complete stranger.” That itself is significant. Then I’ve got a third of those people saying, “Yes, I want to share my regret with a complete stranger, and I want to give him my email address so he can talk to me more about it.” That itself tells us something. And that was a surprise to me. But I think part of it is that we’ve misstated how willing people are to talk about these issues, and in some level, how desperately they want to talk about these issues, because when we take these – and it’s a big part of the process by which we deal with these things – when we take these blobby, negative, abstract emotions and convert them into words by talking about them or writing about them, we defang them –we make them less menacing. We go from the sort of fearsome and abstract to less fearsome and concrete. And that’s important in and of itself, and it helps us begin the sense-making process.

Geoff Mitelman: And you talk about this also – of the work of James Pennebaker, who talks about these kinds of things in a third-person perspective that is really valuable, of being able to say from – almost like a God’s-eye view, of being able to say, “I’m not going to talk about it in the first person, but I’m going to sort of reflect on it and reframe these kinds of questions.” So I’d love for you to share a little bit about that as well.



Daniel H. Pink: Yeah, so let’s wrap it around even sort of a bigger process. Again, you and I were talking very, very briefly, before we got on, about the work of Dave DeSteno, who writes a lot about the value of religion, and religious practice, and religious belief, and looking at scientific evidence of that, which, I think, is quite fascinating. And to me, one of the things that is helpful in religious tradition and religious practice is ritual, because a ritual is a set of steps that you go through. It’s a formula, but it gives people a way to do something and then make sense of things.

And so what I’m trying to do is trying to offer up, based on the science, almost a secular formula for dealing with regret. So, it begins with something called self-compassion. One of the things that we see is that when we talk to ourselves in the face of screw-ups and setbacks, we’re brutal – we’re ridiculous. We talk to ourselves in ways that we would never talk to anybody else. Stop doing that! Treat yourself with kindness rather than contempt. So that’s a big first step. And also just recognize the universality of it. Recognize that your missteps are part of the human condition. It’s not some kind of mark against you. It’s not some kind of intrinsic, debilitating, singular flaw. It is – you’re like everybody else.

So that’s first step. Second step is disclosure and sense-making. So, both disgorging it if you want – but simply the act, as Pennebaker’s work has shown, simply the act of writing about it privately can be a form of reducing the burden and of making sense. And finally is – so you want to go inward and reframe it. You want to go outward and disclose it and make sense of it. And then, finally, you want to move forward by extracting a lesson from it. And here, some of the work that you were hinting at before on self-distancing is very useful. So think about when you’re deciding what to do – take a step back. Talk to yourself in the third person, as you were saying before, or ask yourself what you would tell your best friend to do.

And so, the more we go through this kind of process that becomes almost automatic, that becomes habitual – and because of its habituation, becomes, in a way soothing in the way that certain kinds of religious practice are – “We say, okay, you know what? I’m feeling that spear of regret. All right, treat myself with kindness rather than contempt. I’m going to talk about it or write about it, to disclose and make sense of it. And I’m going to take a step back and say what lesson I’m going to draw from it.”

And that ends up being a way to use regret as a force for good. You don’t get the rumination and debilitating effects on the one side, but you also don’t get the kind of empty-headed, “I’m not going to learn” absence of learning and growth you get by ignoring it. You actually confront it. You think about it, you have a process, and then you derive a lesson from it.

Geoff Mitelman: There’s a line from Kierkegaard that I quote all the time, which is that “life has to be lived forward, but can only be understood backward.”

Daniel H. Pink: Right.



Geoff Mitelman: And being able to say, “I don’t want this to have happened, but it did. So what now?”

Daniel H. Pink: Well, this is the subtitle of the book. The book is Kirekegaardian in that sense, and that the subtitle of the book is how looking backward moves us forward. And this is, again, part of what I’m trying to do to change minds and hearts out there – which is that there is a belief out there that we should never look backward. What’s past is past. Don’t look back, always look forward. And it ends up this idea that we should never look backward – that we should just bat away our regrets, is a widely held point of view in this country, and it is unscientific, and it is not an effective blueprint for living.

Geoff Mitelman: Well, what’s also so interesting and so important is the interplay of emotion and action. You mentioned that emotion is data, right? It tells us how we’re feeling. And oftentimes our emotions are what drive our actions, but sometimes our actions can drive our emotions. And so when we’re thinking about regret, of “How is that going to drive us?” But also being able to say, “let me do some actions to reframe how I’m feeling right now.” Not lessen its power, but lessen its negative sting, so that it’s still very much who we are.

Daniel H. Pink: Absolutely. Right.

Geoff Mitelman: One of the other things that you talk about a lot is the “if only,” versus the “at least.” And that’s a helpful framing, because that can be so painful to look back. And the great study of the Olympic athletes, where the gold medalists are really happy, and the bronze medalists are actually, because “at least I got a medal” – but the silver medalists are thinking, “if only I had gotten a little bit more of a jump on that race, or if I had put my toe in that way on the diving board, it would have been better.” And the silver medalists tend to be sadder than the bronze medalists.


Daniel H. Pink: Well, then part of this is, some of this goes to our incredible brains. Our brains are remarkable, and we can do. You mentioned the word before – counterfactual thinking. We can conjure situations and scenarios that run counter to the actual facts. And there are two kinds of counterfactuals. One of them is a downward counterfactual, where you imagine how things could have been worse. “I shouldn’t have married this guy, but at least I have these two great kids,” all right? That’s a common regret that I saw in the database.

And the thing is, you also use the word “sting.” And at least these downward counterfactuals can take the sting out of certain kinds of regrets. They can make us feel better. So at least downward counterfactuals make us feel better, but they don’t make us do any better. And it’s okay to feel better. I have nothing against feeling better, but they actually don’t lead to actual growth and improvement.

Now, “if only” – that is an upward counterfactual, imagining how things could have turned out better. They make us feel worse, but they help us do better.

And here’s the thing – and this is the thing that a lot of people that don’t like. M<y view – and I think the science tells us very clearly – that regret clarifies what we value and instructs us how to do better. And most of us want that clarification, and most of us want that instruction. However, regret also is uncomfortable. It hurts a little bit. And you can’t get the clarification or the instruction without the discomfort. It comes as a whole package. You can’t order it a la carte, and that’s what people don’t want. And so they’re unwilling to deal with the discomfort, even though they want the clarification and the instruction. What we want, essentially, is something for nothing. And that’s not how emotions work. That’s not how human beings grow.

Geoff Mitelman: There’s also, there’s a book by Jesse Singal called The Quick Fix, about how a lot of popular, always – there’s been sort of a kernel of accuracy in psychology, but then gets expanded out because I think people want to say, like, “Oh, if I do this – if I smile more, I’ll be happier,” and a very quick resolution when, in fact, life is very complicated and very messy and can be painful, and we don’t want to feel that. And if we don’t feel that, then we’re not able to actually grow and become fuller human beings.

Daniel H. Pink: And I want you to have plenty of positive emotions. And I want to have plenty of positive emotions. And I want everybody listening to this to have plenty of positive emotions. And you want to have more positive emotions than negative emotions. But a life of only positive emotions is not a life well-lived. A life of only positive emotions is not a life with growth, and learning, and meaning, and significance. We all have negative emotions – they’re part of the human condition, and we can learn from them. We can use them as engines to grow. Here we go – I’ve said this before, but I think it bears repeating. Let’s take grief – terrible emotion. Would you want to wave your rabbinical wand if you could and extinguish grief everywhere it lives in the world? I don’t think you would.

Geoff Mitelman: Right.

Daniel H. Pink: Because… why do we grieve? We grieve because we love.



Geoff Mitelman: That’s such a great point. Because I was doing a funeral a couple of weeks ago, and he was a young man, and the family was crying most of the time, as they should, because it was a tragedy. And afterwards, and almost every time when there’s an intake, actually, they walk away feeling better because they’ve had a chance to be able to share how they’re feeling. And it’s never going to go away. The grief is never going to go away, but it’s because “I was able to love somebody.” And I think that’s a terrific, terrific point.

So there was a question that came up in the chat, which was, “How would you suggest living a life when you do anything you want, yet religion might tell you to live a certain way or not to do?” If I’m understanding the question, I think there’s a belief also in sort of Western society, and you mentioned a little bit about Jonathan Haidt’s work about moral foundations, and the different ways in which we think about morality. But there’s a belief in America of, like, “you do you, live your life, no regrets.” There’s a value of individuality, and religion can constrain that, for better or for worse.

So I think religion can also create more regrets. I’m thinking of people who may be in the LGBTQ community and of a more conservative bent, and regret not coming out – or of regretting different things for people who are from a religious perspective, where I might regret something that for you doesn’t matter. Like, “oh, I ate a piece of pork, and I really regret that.” And for you, doesn’t matter. Where does religion and rules come in, in these questions of what we might regret?

Daniel H. Pink: Well, this category of moral regrets – which is, “if only I’d done the right thing,” is more – it’s interesting, because it’s the smallest category, but there’s a great deal of variation within the category. So most of us would agree, I think, have, across social class, across nationalities, have a sense that speaking up is bolder than staying silent, that starting a business is bolder than sticking in a lackluster job, that saving money is more prudent than spending it wildly.

But when it comes to morality, as you say, there’s some consensus – but it’s not full consensus. So somebody might regret – An observant Jew, a Jew who is an Orthodox jew, might regret having a piece of bacon, and a reformed jew might not. And you know what? Who’s right? Yes, “everybody’s right” – you can’t say that.

I’ll give you a less religiously soaked example of that, which is, we had people who regretted – Americans who regretted not serving in the military. And the reason they regretted not serving in the military wasn’t because they missed out on the adventure, [it was] because they felt that they had a duty to serve. And there are other people who looked at that and said, “What are you talking about? We don’t have conscription in this country. And it’s up to you.”

And these people said, “No, I actually feel like it’s a patriotic duty and I’ve breached my patriotic duty.” Who’s right? It’s in the eye of the beholder. And so there were people who – we have a consensus on some things, like in the Ten Commandments. “Don’t steal.” So when people steal, most people think that’s probably a bad thing. I was surprised by how much regret there was over another – the seventh commandment, which is cheating on your spouse. There was a lot of that, and there was a lot more of it than I ever expected and a lot more regret about it than I ever expected. So the moral regrets are – I’ve got to think that what you have to do in a lot, I think you have to have a lot of openness and respect for other people’s moral code. And not to say that yours is better – and again, not to be controversial here, but I think one of the things that John Haidt’s work shows is that political liberals are actually, in some ways, less open-minded than political conservatives about that. So a lot of political liberals don’t have a sense that duty is a moral obligation, that sanctity is a moral obligation, that purity is a moral obligation to some people. To me, what was fascinating is that you have this tiny category with all kinds of variation and controversy swirling within it.

Geoff Mitelman: Yeah, I love that book. That book was kind of revelatory to me.

Daniel H. Pink: Yeah, me too.

Geoff Mitelman: You Know, I also want to have another compared to another author because you mentioned Kristen Neff, who does a lot of work about self compassion. I also want to also recommend her, because I think that’s something that’s hard to be able to feel, because we often think about the importance of self-esteem or self-confidence – but self compassion, that’s a whole different perspective. And it’s not letting yourself off the hook, but being able to say, in the same way that you try to understand somebody else might have been acting in a different kind of way – how would you treat your friend, your best friend here – to be able to treat ourselves in that way? That can be very challenging.

Daniel H. Pink: Yeah, I’ll span religious traditions here and be your hallelujah chorus for both of those. So Kristen Neff is a pioneering researcher in something called, as Jeff is saying, self-compassion. She has several books. Just go to self-compassion.org to look at her stuff. I found it revelatory. And then the book that we were talking about is called The Righteous Mind by John Haidt, and it’s out in paperback. And I found that a revelatory book also.

Geoff Mitelman: Yeah, both of these books are now almost ten years old, but maybe even more, but still so relevant, and speak to so many of these questions here.

Well, I know we’re coming towards the end of our time together, so I would love if you could give any advice for people to be able to say – when we think about regret, what should be our takeaway about the feelings of regret and how it can actually be used in a positive way. If you were to say, like – if you could wave a magic wand and have everybody in the world respond to regret in an appropriate way, in a constructive way, what would that look like?

Daniel H. Pink: Treat yourself with kindness. Write about it or talk about it to make sense of it, and explicitly draw a lesson from it to do better next time. That’s it. And again, even though that is a quote-unquote “process” and it has steps – and like any kind of process, you have to be deliberate in going through it at first – at a certain point, it becomes habitual. And that’s when there’s this paradox where you end up actually dealing with your regrets so effectively you have fewer of them going forward.



Geoff Mitelman: There’s a person I love on Twitter, Tim Urban, who has the “Wait, but Why?” And he shared this out a couple before, but he does a little tree of what our life is. And we think that everything’s been closed off, because we had all these things that happen in our life that are now closed off. But what we don’t realize is how many opportunities there are in front of us., and being able to look back and say, “these were the things that I regret” – that’s not a bad thing. It’s a human thing. And trying to avoid that ultimately makes our lives worse. But being able to look at it effectively and appropriately, that’s the best thing to be able to do.

Daniel H. Pink: I’ll see you and raise you. I mean, I think that if we are able to reckon with our regrets properly, it’s the most transformative emotion we have.



Geoff Mitelman: What a wonderful way towards closing, here, to be able to have this way of thinking through as we’re about to celebrate – at least we’re speaking at the end of March of ’22, and Passover is coming up. And there’s a line from Rabbi Lawrence Kushner, who talks about redemption, because the story of Passover is about redemption. And he shares this story of redemption. He draws the analogy of when he was a kid, he used to bring little stamps, and you could redeem those stamps for something that you want – or actually, I just was on an airplane, like, you can redeem your miles for more trips. And redemption is taking something that seems useless and turning it into something that is flourishing and incredibly valuable. And so, being able to redeem the idea of regret, being able to say it feels uncomfortable – it feels yucky, we don’t like it, but it’s the core of being able to grow and really create a more flourishing life and a more flourishing society.

So, Dan, thank you so much for not just your time, but for all the wisdom that you have. And here is the book called the Power of Regret. You can get it wherever books are sold. And if people want to follow you, as they should, it’s @Danielpink, correct?

Daniel H. Pink: Yeah, I’m at @Danielpink on Twitter, and my website is danpink.com. So, all kinds of good stuff there, all of it free.

Geoff Mitelman: So follow him and sign up. Next week we will be talking with Professor Rebecca Saxe of MIT, who does work about moral philosophy and moral psychology and theory of mind. She is going to talk about some of these questions next Tuesday at 03:00 p.m. But thank you all for joining us. And Daniel, thank you so much for your time with us today.



Daniel H. Pink: Thanks for having me. It was a real pleasure.

Geoff Mitelman: Terrific. Thank you.