The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

We shouldn’t doubt the sincerity of people who say they have no regrets. Instead, we should think of them as actors playing a role—and playing it so often and so deeply that they begin to believe the role is real. Such psychological self-trickery is common. Sometimes it can even be healthy. But more often the performance prevents people from doing the difficult work that produces genuine contentment.

That’s because negative emotions are essential, too. They help us survive. Fear propels us out of a burning building and makes us step gingerly to avoid a snake. Disgust shields us from poisons and makes us recoil from bad behavior. Anger alerts us to threats and provocations from others and sharpens our sense of right and wrong. Too much negative emotion, of course, is debilitating. But too little is also destructive.

begin with the reclamation project. In Part One—which comprises this chapter and the next three—I show why regret matters. Much of this analysis taps an extensive body of scholarship that has accumulated over the last several decades. Economists and game theorists, working in the shadow of the Cold War, began studying the topic in the 1950s, when obliterating the planet with a nuclear bomb was the ultimate regrettable act. Before long, a few renegade psychologists, including the now legendary Daniel Kahneman and Amos Tversky, realized that regret offered a window into not only high-stakes negotiations but the human mind itself.

These seventy years of research distill to two simple yet urgent conclusions: Regret makes us human. Regret makes us better.

In just a few words, this fifty-two-year-old woman from Virginia pulls off a stunning feat of cerebral agility. Discontent with the present, she mentally returns to the past—decades earlier, when she was a young woman contemplating her educational and professional path. Once there, she negates what really happened—giving in to her father’s wishes. And she substitutes an alternative: she enrolls in the graduate program she prefers. Then she hops back in her time machine and hurtles forward. But because she’s reconfigured the past, the present she encounters when she arrives is vastly different from the one she left moments earlier. In this newly remodeled world, she’s satisfied, fulfilled, and accomplished.

The seven-year-olds “performed very similarly to adults on the measures of the understanding of regret,” Guttentag and Ferrell write. Seventy-six percent of them understood that David would likely feel worse. But the five-year-olds showed little understanding of the concept. About three-fourths of them said the boys would feel the same.

That’s why most children don’t begin to understand regret until age six.[6] But by age eight, they develop the ability even to anticipate regret.[7] And by adolescence, the thinking skills necessary to experience regret have fully emerged.[8] Regret is a marker of a healthy, maturing mind.

It is so fundamental to our development and so critical to proper functioning that, in adults, its absence can signal a grave problem. An important 2004 study makes that plain. A team of cognitive scientists organized a simple gambling game in which participants had to choose one of two computerized roulette-style wheels to spin. Depending on where the arrow landed on their chosen wheel, they would either win money or lose money. When participants spun a wheel and lost money, they felt bad. No surprise. But when they spun a wheel, lost money, and learned that if they’d chosen the other wheel, they’d have won money, they felt really bad. They experienced regret.

In short, people without regrets aren’t paragons of psychological health. They are often people who are seriously ill.

The emotion becomes regret only when she does the work of boarding the time machine, negating the past, and contrasting her grim actual present with what might have been. Comparison lives at regret’s core.

What nudges her fully into the realm of regret is the reason that alternative doesn’t exist: her own decisions and actions. She’s the cause of her own suffering. That makes regret different—and far more distressing—than a negative emotion like disappointment. For instance, I might feel disappointed that my hometown basketball team, the Washington Wizards, didn’t win the NBA championship. But because I neither coach the team nor suit up for games, I’m not responsible and therefore can’t regret it. I just sulk and wait until next season.

Only 1 percent of our respondents said that they never engage in such behavior—and fewer than 17 percent do it rarely. Meanwhile, about 43 percent report doing it frequently or all the time. In all, a whopping 82 percent say that this activity is at least occasionally part of their lives, making Americans far more likely to experience regret than they are to floss their teeth.

In fact, I have yet to uncover a study disconfirming the ubiquity of this emotion. (And believe me, I’ve looked hard.) Scholars in every field, approaching the subject from different directions and using a variety of methodologies, arrive at the same conclusion: “To live, it seems, is to accumulate at least some regrets.”

Like all of us, she’s frequently climbed aboard her mental time machine to rewrite a story, comparing what is to what might have been and taking responsibility for the gap.

The athletes who finished third appeared significantly happier than those who finished second. The average rating of the facial expressions of bronze medalists was 7.1. But silver medalists—people who’d just placed second in the most elite competition in the world—were neutral, even tilting slightly toward unhappy. Their rating: 4.8.

Counterfactuals can point in either of two directions—down or up. With “downward counterfactuals,” we contemplate how an alternative could have been worse. They prompt us to say “At least . . .”—as in, “Sure, I got a C+ on that exam, but at least I passed the course and don’t have to take it again.” Let’s call these types of counterfactuals At Leasts. The other variety are known as “upward counterfactuals.” With upward counterfactuals, we imagine how things could have gone better. They make us say “If only . . .”—as in, “If only I’d attended class more often and done all the reading, I’d have gotten a much better grade.” Let’s call these counterfactuals If Onlys.

When researchers reviewed competitors’ post-event television interviews, they found the bronze medalists happily humming At Leasts. “At least I didn’t finish fourth. At least I got a medal!” Silver medalists, though, were wracked with If Onlys. And that hurt. “Second place is only one step away from the cherished gold medal and all of its attendant social and financial rewards,” Medvec and her colleagues wrote. “Thus, whatever joy the silver medalist may feel is often tempered by tortuous thoughts of what might have been had she only lengthened her stride, adjusted her breathing, pointed her toes, and so on.”[2]

But the Medvec-Gilovich-Madey study has been replicated. Even its replications have been replicated. For example, David Matsumoto of San Francisco State University assembled about 21,000 photographs from the men’s and women’s judo competitions at the 2004 Olympic Games in Athens, a massive photo set that represented 84 athletes from 35 countries. Regardless of the national origin or ethnicity of the athletes, the difference in facial expression among the medalists was striking. During the podium ceremonies, the gold medalists were almost all smiling widely (what’s called a “Duchenne smile”). So, too, were most of the bronze medalists. The silver medalists? Not so much. They smiled only one-fourth as much as their counterparts.

One study found that 80 percent of the counterfactuals people generate are If Onlys. Other research puts the figure even higher.

Regret is the quintessential upward counterfactual—the ultimate If Only. The source of its power, scientists are discovering, is that it muddles the conventional pain-pleasure calculus.[10] Its very purpose is to make us feel worse—because by making us feel worse today, regret helps us do better tomorrow.

We often compound bad choices by continuing to invest time, money, and effort in losing causes instead of stanching our losses and switching tactics. We increase funding in a hopeless project because we’ve spent so much already. We redouble efforts to salvage an irredeemable relationship because we’ve already devoted a few years to it. The psychological concept is known as “escalation of commitment to a failing course of action.” It’s one of the many cognitive biases that can pollute our decisions. It’s also something that experiencing regret can fix. Gillian Ku, now of London Business School, found that getting people to think about a previous escalation of commitment, and then to regret it, decreased their likelihood of making the error again.[1] Inducing this unpleasant feeling of If Only improved their future behavior.

During the pandemic of 2020–21, you hastily purchased a guitar, but you never got around to playing it. Now it’s taking up space in your apartment—and you could use a little cash. So, you decide to sell it. As luck would have it, your neighbor Maria is in the market for a used guitar. She asks how much you want for your instrument. Suppose you bought the guitar for $500. (It’s acoustic.) No way you can charge Maria that much for a used item. It would be great to get $300, but that seems steep. So, you suggest $225 with the plan to settle for $200. When Maria hears your $225 price, she accepts instantly, then hands you your money. Are you feeling regret?

For example, in 2002, Adam Galinsky, now at Columbia University, and three other social psychologists studied negotiators who’d had their first offer accepted. They asked these negotiators to rate how much better they could have done if only they’d made a higher offer. The more they regretted their decision, the more time they spent preparing for a subsequent negotiation.[3] A related study by Galinsky, University of California, Berkeley’s, Laura Kray, and Ohio University’s Keith Markman found that when people look back at previous negotiations and think about what they regretted not doing—for example, not extending a strong first offer—they made better decisions in later negotiations. What’s more, these regret-enhanced decisions spread the benefits widely. During their subsequent encounters, regretful negotiators expanded the size of the pie and secured themselves a larger slice. The very act of contemplating what they hadn’t done previously widened the possibilities of what they could do next and provided a script for future interactions.[4]

This is one of the central findings on regret: it can deepen persistence, which almost always elevates performance.

Then the researchers examined what happened to these scientists’ careers. People in the narrow-miss If Only group systematically outperformed those in the narrow-win At Least group in the long run. These Silver Emmas of science were subsequently cited much more often, and they were 21 percent more likely to produce a hit paper. The researchers concluded that it was the setback itself that supplied the fuel. The near miss likely prompted regret, which spurred reflection, which revised strategy, which improved performance.

When you feel the spear of regret, you have three possible responses. You can conclude that feeling is for ignoring—and bury or minimize it. That leads to delusion. You can conclude that feeling is for feeling—and wallow in it. That leads to despair. Or you can conclude that feeling is for thinking—and address it. What does this regret tell you? What instructions does it offer for making better decisions? For improving your performance? For deepening your sense of meaning?

More important, as Roese and Summerville note, the previous research relied on “samples of convenience” rather than representative slices of the total population. In one study, researchers asked graduate students to hand out questionnaires to people they knew, not exactly the gold standard for random sampling. The study of retired people surveyed 122 older adults living near Purdue University—even though it’s unlikely that as western Indiana goes, so goes the rest of the world. In another study, the interviewees were a bricolage of ten emeritus professors, eleven nursing home residents, forty undergraduate students, and sixteen clerical and custodial staff. Roese and Summerville noted that 73 percent of the total sample in their meta-analysis were women, hardly the gender ratio that statistics best practices demand. An overwhelming number of the people surveyed were White. Even the Gallup polls, which were more representative of the U.S. population, often produced less than definitive results. In the 1953 poll, 15 percent of people chose education as their single biggest regret. But an even larger portion—about 40 percent—gave more than one answer to the question. What was needed, Roese and Summerville concluded toward the end of their paper, was a survey that represented the diversity and complexity of the entire country. And in 2011, Roese and his colleague Mike Morrison took up the challenge. They reached beyond the college campus with a telephone poll of 370 people fro...

However, while the earlier study suggested that regret lurked in realms where people perceived lots of opportunities, this study found the opposite. Areas where the opportunities had vanished—for instance, considering oneself too old for additional education—produced the most regrets. Such low-opportunity regrets (in which a problem could not be fixed) outnumbered high-opportunity regrets (in which a problem could be fixed) by a solid margin.

Three men with regrets that span a wide swath of territory—an Australian marriage, a Canadian childhood, a California election. But how different, really, are they? All involve a moral breach. At a moment in their lives now stamped in memory, all three faced a choice: Honor their principles or betray them? And at that moment, all three chose wrongly. On the surface, their regrets poke through different patches of life’s landscape. Below the surface, they grow from common roots.

During one of my conversations with Jason, I told him he reminded me of the grasshopper. He shook his head ruefully. “I never took steps to prepare,” he said. During the summer of his life, there were “a lot of cavalier moments where I enjoyed saying ‘So what?’ and just rolling through it.” But in the end, he said, it “was twenty-five years of fiddling.”

Temporal discounting is only the beginning, because this deep structure category involves a second time-based issue. Some regrets deliver their pain immediately. If I race my car down the street well above the speed limit and collide with another vehicle, the consequences of the decision, and therefore my regret, are instantaneous. A totaled vehicle, an aching back, a lost day. But foundation regrets don’t arrive with the sound and fury of a collision. They proceed at a different pace.

Compounding. It’s a powerful concept, but one our grasshopper minds struggle to comprehend. Suppose I offered you a choice—$1 million in cash today or one penny that will double in value every day for a month. Most people, experimental evidence shows, would opt for the million bucks.[4] And during the first three and a half weeks of our pact, that decision would seem wise. But after just a little more time—on day thirty—that penny would become more than $5 million. We can explain the power of compounding with another chart, which you’ll notice is essentially the mirror image of its predecessor.

Embedded in each of these regrets is a solution. Just as foundation regrets can be defined with a well-worn fable, one response to them is contained in a hoary Chinese proverb: The best time to plant a tree is twenty years ago. The second-best time is today.

One of the most prevalent cognitive biases—in some ways the über-bias—is called the “fundamental attribution error.” When people, especially Westerners, try to explain someone’s behavior, we too often attribute the behavior to the person’s personality and disposition rather than to the person’s situation and context.

“It was truly as if we had known each other our whole lives,” Bruce told me recently. “And I have never felt that way again.” The train chugged on. The hours raced by. Just before midnight, as the train was approaching a station in Belgium, the woman stood up and told him, “I have to go.” “I’ll come with you!” Bruce said. “Oh, God,” she replied. “My father would kill me!” They walked through the train aisle to the door. They kissed. Bruce madly scribbled his name and his parents’ Texas address on a slip of paper and handed it to her. The train doors parted. She stepped off. The doors closed. “And I just stood there stunned,” said Bruce, who is now in his sixties and who asked that I not use his last name. When he returned to his seat, his fellow passengers asked why he hadn’t left the train with his girlfriend. “We just met!” Bruce told them. He didn’t even know her name. They hadn’t exchanged names, Bruce explained, because “it was almost as if we already knew.” The following day, having made it to Stockholm, Bruce boarded a flight back to the United States. Forty years later, when he completed the World Regret Survey, he relayed this tale and concluded, “I never saw her again, and I’ve always wished I stepped off that train.”

If foundation regrets arise from the failure to plan ahead, work hard, follow through, and build a stable platform for life, boldness regrets are their counterpart. They arise from the failure to take full advantage of that platform—to use it as a springboard into a richer life.

A key reason for this discrepancy is that when we act, we know what happened next. We see the outcome and that can shrink regret’s half-life. But when we don’t act—when we don’t step off that metaphorical train—we can only speculate how events would have unfolded.

Human beings are impressive creatures. We can fly planes, compose operas, and bake scones. But we generally stink at divining what other people think and anticipating how they will behave. Worse, we don’t realize how inept we are at these skills.[3] And when it comes to perceiving and predicting awkwardness, we’re next-level bunglers.

What’s going on in these situations is a phenomenon that social psychologists call “pluralistic ignorance.” We mistakenly assume that our beliefs differ vastly from everyone else’s—especially when those private thoughts seem at odds with broader public behavior. So, when we struggle to understand a lecture, we don’t ask questions because we erroneously believe that because other people aren’t asking questions, that means they understand—and we don’t want to look dumb. But we don’t consider that other people might be equally befuddled—and equally nervous about seeming stupid. We’re confused, but we stay confused because we falsely believe nobody but us is confused!

Close relationships, more than money or fame, are what keep people happy throughout their lives. . . . Those ties protect people from life’s discontents, help to delay mental and physical decline, and are better predictors of long and happy lives than social class, IQ, or even genes. That finding proved true across the board among both the Harvard men and the inner-city participants.[7]

What give our lives significance and satisfaction are meaningful relationships. But when those relationships come apart, whether by intent or inattention, what stands in the way of bringing them back together are feelings of awkwardness. We fear that we’ll botch our efforts to reconnect, that we’ll make our intended recipients even more uncomfortable. Yet these concerns are almost always misplaced. Sure, we’ll get rebuffed sometimes. But more often—much more often, in fact—we overestimate how awkward we’ll feel and underestimate how much others will welcome our overtures.

The lesson of closed doors is to do better next time. The lesson of open doors is to do something now. If a relationship you care about has come undone, place the call. Make that visit. Say what you feel. Push past the awkwardness and reach out.

Take, for example, the education level of respondents. People with college degrees were more likely to have career regrets than people without college degrees. At first that might seem surprising. Having a college degree generally affords people a wider set of professional options. But that could be precisely why college graduates have more career regrets. Their lives presented more opportunities—and therefore a larger universe of foregone opportunities. Income presented a similar pattern. Regrets about finance, not surprisingly, correlated tightly with household income—the lower the household income, the more likely someone was to have a finance-related regret. But regrets about careers ran in the reverse direction. That is, the higher the income, the more likely it was that someone had a career regret. Again, more opportunities could beget more regrets about unrealized opportunities.

Thirty years ago, nearly fresh out of college, I went to law school. I regret it. It wasn’t a calamity. It was just a poor decision. If only I’d made a wiser choice, perhaps by waiting longer or by choosing an entirely different trajectory, I could have devoted those years to endeavors more fulfilling and better for the world—and I would have struggled less in the early years of my working life. But I also met my wife in law school, which was a glorious triumph for my well-being. I can’t undo an action regret like this. But one way to ease its sting is to switch from If Only to At Least. Going to law school was a mistake—but at least I met my wife.

“I regret marrying a loser,” they would say, “but at least I’ve got these great kids.” Finding a silver lining doesn’t negate the existence of a cloud. But it does offer another perspective on that cloud.

Over 195 trials, people’s preferences were clear. They loved talking about themselves—so much, in fact, that they were willing to take significantly less money for doing that than for any other behavior. “Just as monkeys are willing to forgo juice rewards to view dominant groupmates . . . individuals were willing to forgo money to disclose about the self,” Tamir and Mitchell wrote.

The study, the researchers concluded, “provided both behavioral and neural evidence that self-disclosure is intrinsically rewarding.”

Self-disclosure is especially useful with regret. Denying our regrets taxes our minds and bodies. Gripping them too tightly can tip us into harmful rumination. The better approach is to relive and relieve. By divulging the regret, we reduce some of its burden, which can clear a path for making sense

The explanation—and the reason self-disclosure is so crucial for handling regret—is that language, whether written or spoken, forces us to organize and integrate our thoughts. It converts blobby mental abstractions into concrete linguistic units. That’s a plus for negative emotions.

Its opposite, self-esteem, can be more effective. Highly prized in certain parenting and education circles, where praise gushes and participation trophies gleam, self-esteem measures how much you value yourself. How good do you feel about who you are? How favorably do you evaluate your traits and behaviors? For example, in surveys, people with high self-esteem award themselves top marks for their looks, their brains, and their popularity—while people with low self-esteem make the opposite assessment. (Curiously, neither evaluation correlates with how smart, attractive, or popular someone actually is.)