Daniel Pink is the author of several bestselling books that probe human behaviors, including the importance of timing, the mechanism behind motivation, and the sociology of selling things. His new book, The Power of Regret: How Looking Back Is Moving Us Forward, is about the wrongheadedness of the No Regrets credo. He spoke with TIME about why highlighting failure and regret is crucial in business.
This interview has been condensed and lightly edited.
Why write a book on regret?
The external reason is that we’ve gotten it profoundly wrong. If we do not understand this emotion, then we are leaving its capability on the table by having this bizarrely aversive relationship with it. For me personally, largely because I have regrets of my own. I can’t imagine having written this book in my 30s. But in my 50s, it felt kind of inevitable because I had mileage behind me and mileage ahead of me, and when I talked to people about it, I got the exact opposite response to what I expected.
You conducted the World Regret Survey in which you asked people about their biggest regrets during 2020, in the teeth of the pandemic. Do you think that time made people more reflective about how they could have lived our lives differently? Or do you think it obscured their ability to see their former lives with objectivity?
I do think that that people were willing to reflect at that moment, if for no other reason than they had extra time. And a sense of mortality was in the air. It made people more willing to look backward and ask some of those fundamental questions.
Read More: How Regrets Can Lead to Smarter Decisions
You write about four core categories of regret— foundation regrets, boldness regrets, moral regrets, and connection regrets. Can you explain the difference between them?
Foundation regrets are about stability: finances, health, about studying in school and university. Boldness regrets are about “if only I’d taken the chance,” a very large category of regrets. Moral regrets are complicated; we have a lot of regrets, in this database of 16,000, about bullying. We have a lot of regrets about marital infidelity. I think to most people around the world and of different political perspectives, those are bad things. I think it gets super interesting in the very small category of things. For instance, I showed a left-leaning American a regret a lot of people had about not serving in the military and he said ‘That’s not a regret.’ But if you believe in a sense of duty, that’s a different moral code. It’s not wrong, it’s not better or worse.
And then connection regrets are about losing touch with somebody in your life or when there’s been a schism ?
It’s not so much schisms as much as drifts. It’s a relationship that should have been intact, or that was intact, and it comes apart. And I think one reason we missed the significance of this is that these relationships often come apart in profoundly undramatic ways. It’s not this people throwing plates at each other, it’s a slow kind of drift. And then one person doesn’t want to reach out because they think it’s going to feel awkward and they think the other side’s not going to care. And they’re wrong.
Which is the largest category?
Connection regrets. Moral is the smallest, but there’s something about those that really stick with people. There’s somebody in my book who stole candy from a grocery store when she was 10. And at age 70, she’s still bugged about that.
Is there a difference between using regret as a tool and learning from our mistakes?
They’re certainly related. The problem is that is that some people make mistakes and don’t feel bad about them. Mistake is an action; regret is a feeling. The thing about regret is that it hurts. And it hurts for a reason; it’s conveying a particularly strong signal. The fact that I feel a spear of negative feeling called regret makes it much more likely that I’m going to be awake to the possibility of learning from that mistake, if I treat it right.
Some of the regrets people had seemed to be predicated on a genetic lottery. If you were lucky enough to be born into a wealthy family, isn’t it likely you’d have fewer foundational regrets?
I do think that in some cases, boldness presupposes some degree of stability. It’s harder to be bold if your life is completely precarious. Regret requires some degree of agency— it’s your fault. And for certain kinds of foundation regrets, you don’t always have agency. A good example of this is saving money. If you regret that you didn’t build that stable financial foundation, and you’re an American, and you’re the first one in your family to go to college, and you racked up $200,000 of student debt, that’s not all on you.
Can feelings of regret make you a better leader?
If you deal with it right. Ignoring regret is a really bad idea for leaders, because they’re not going to learn. But wallowing in it is, in some ways, an even worse idea because it hobbles them. What I would like for leaders is not to sort of proclaim No Regrets as this sign of courage, but actually to show courage by staring their own regrets in the eye and doing something about them, and having honest, authentic conversations with their team about regrets. If we deal with regrets sensibly, they are powerful forces for improving us and for leaders especially, there’s evidence showing that confronting your regrets can make you a better negotiator, it can make you a better strategist and make you a better problem solver. There’s even evidence—and I think a lot of leaders don’t get this because it’s counterintuitive—that disclosing those regrets and mistakes, actually strengthens your standing and builds affinity rather than the reverse.
Don’t leaders have to have a slightly ‘no regrets’ philosophy in order to make the bold moves that risk a lot of money and people’s livelihoods, to have, as they say, a bias towards action?
I don’t think that having a bias toward action is actually being ‘no regrets’. I think that leaders can look at the four core regrets that I’ve identified and have a pretty good sense that when they look back on their leadership, those are going to be the things that they regret. Did they create a stable environment for people? Did they do the right thing? Did they build connections and affinity? And did they take the smart risks? Management books talk about a bias for action but in the day to day choices of many managers, there’s a bias toward inertia, there’s a bias toward not getting in trouble.
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Can we regret the wrong thing? Like perhaps, just to pick an example out of the air, an executive is forced to resign because he did not reveal a relationship with an employee. He now regrets not revealing that relationship earlier, but perhaps what he should have regretted was engaging in the relationship at all? How can we tell what the right regret is?
I don’t think there is a foolproof way of doing that. What you’re talking about is, in some ways, a moral regret. And I think it depends on that individual’s moral code, whether the breach was the relationship itself or not disclosing it. That depends on a lot of different things —whether the parties were married, what the company policies were, and so forth. I do think that it’s possible for people to feel regret for the wrong thing. It might be a half step to the ‘no regrets’ thing. So they’re not actually really confronting it. In that particular case, if you say, ‘Oh, I regret that I didn’t reveal it,’ maybe you are eliding the fact that what you should be regretting is the is the relationship itself.
Is there a difference between ruefulness and regret? A business leader might say, ‘I wish I’d invested in infrastructure.’ But if they’d done that, they couldn’t have hired people. How do you make the distinction?
One of my favorite techniques in the book is the idea of a failure resume. This is an idea from Tina Seelig at Stanford, where what you do is you list your mistakes, your setbacks, your screw ups, in the way that you would on a resume, but then in the next column, you list what you learned from it. When I’ve done that, it’s painful, it’s unpleasant. But there are a couple of times when the lesson was, stuff happens. I didn’t have the right information at the time. That sense-making process is a way to defang some of those regrets.
What can a boss do if they have a conversation with an employee that he or she regrets?
It depends on what the conversation is. This is the difference between a regret of action or inaction. Obviously action regrets are easier to address, because you can just undo them. You can’t erase them fully, but you can apologize, you can make amends, you can make restitution, you can explain. And I think that’s perfectly fine. If it’s an inaction regret, if you didn’t speak up on behalf of somebody, if you didn’t have somebody’s back at a meeting, you can’t undo that. But what you should do is look hard at yourself, disclose the regret, make sense of it, and extract a lesson from it, and that’s the most important thing.
Your steps of remedy seem very similar to the way people who have faith deal with what they call sins. You confess, you repent, you make amends, and you live differently. Would not your process be a very familiar one to, say, Catholics?
Our brains are programmed for positive emotions and negative emotions, because negative emotions are functional. And our most common negative emotion is regret, because it’s also the most instructive and clarifying. So the fact that religious traditions have figured this out and tried to reckon with it is a great sign. And the fact that their steps are similar to the steps science suggests, is also a great sign. What’s not a great sign is the utter capture of kind of broader cultural philosophy that suggests that you shouldn’t have regrets, you should never look backward. And that if you have a negative feeling, it should be banished.
What is your personal biggest regret?
I guess the one that really sticks with me is regrets about kindness when I was younger. I was never a bully. But I was somebody who grew up to become a writer. So I was an O.K. observer, and I would see stuff. And I would see people being excluded, and I would see people being mistreated. And I didn’t do a damn thing. That really bugs me, even to this day. I learned from that regret. What I don’t want to do is in the future 25 years come back and say, ‘Man, you know what, you were not very kind when you were in your 20s. And you were also kind of an ass when you were in your 50s, too.’
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