The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

“Though we would like to live without regrets, and sometimes proudly insist that we have none, this is not really possible, if only because we are mortal.” James Baldwin, 1967

Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human. Regret is also valuable. It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up.

For example, human beings also hold what amounts to a portfolio of emotions. Some of these emotions are positive—for example, love, pride, and awe. Others are negative—sadness, frustration, or shame. In general, we tend to overvalue one category and undervalue the other. Heeding others’ advice and our own intuitions, we stuff our portfolios with positive emotions and sell off the negative ones. But this approach to emotions—to jettison the negative and pile on the positive—is as misguided as the approach to investing that prevailed before modern portfolio theory.

The purpose of this book is to reclaim regret as an indispensable emotion—and to show you how to use its many strengths to make better decisions, perform better at work and school, and bring greater meaning to your life.

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

Nearly all regrets fall into four core categories—foundation regrets, boldness regrets, moral regrets, and connection regrets.

Regret is a marker of a healthy, maturing mind.

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.

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.

“When you find yourself in a hole, stop digging.” And perhaps you’ve ignored this law. 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.

A look at the research shows that regret, handled correctly, offers three broad benefits. It can sharpen our decision-making skills. It can elevate our performance on a range of tasks. And it can strengthen our sense of meaning and connectedness.

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

“I remember the bitterness of the taste of regret. So when something is sweet, good god, it’s so much sweeter.”

When it comes to regret, a third view is healthier: Feeling is for thinking. Don’t dodge emotions. Don’t wallow in them either. Confront them. Use them as a catalyst for future behavior. If thinking is for doing, feeling can help us think.

Likewise, framing regret as an opportunity rather than a threat helps us transform it—so that it operates as a sharp stick rather than a leaden blanket. Regrets that hurt deeply but dissolve quickly lead to more effective problem solving and sturdier emotional health.

Kintsugi (which translates to “golden joinery”) considers the breaks and the subsequent repairs part of the vessel’s history, fundamental elements of its being. The bowls aren’t beautiful despite the imperfections. They’re beautiful because of the imperfections. The cracks make them better. What’s true for ceramics can also be true for people.

The best time to plant a tree is twenty years ago. The second-best time is today.

Our actual self is the bundle of attributes that we currently possess. Our ideal self is the self we believe we could be—our hopes, wishes, and dreams. And our ought self is the self we believe we should be—our duties, commitments, and responsibilities.[1]

“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.

At Leasts can turn regret into relief. On their own they don’t change our behavior, but they change how we feel about our behavior, which can be valuable. And because At Leasts spring to mind naturally far less often than If Onlys, we must summon them ourselves at the right time. At Leasts work like antibiotics. Sometimes we need to reach into the medicine cabinet and pop a few of them to fortify our psychological immune system and fight off certain harmful emotions.[4] If we use these antibiotics too often, their efficacy will wane. If we use them intelligently, they can aid in healthy functioning.

Again, regret can make us better when we use emotions as a signal for our thoughts. When feeling is for thinking, and thinking is for doing, regret can perform its decision-enhancing, performance-boosting, meaning-deepening magic. Writing about regret or revealing a regret to another person moves the experience from the realm of emotion into the realm of cognition. Instead of those unpleasant feelings fluttering around uncontrollably, language helps us capture them in our net, pin them down, and begin analyzing them.

A self-compassionate approach does not foster complacency, as some might fear.[27] While self-flagellation seems motivating—especially to Americans, whose mental models of motivation often begin with howling, red-faced, vein-popping football coaches—it often produces helplessness. Self-compassion, by contrast, prompts people to confront their difficulties head-on and take responsibility for them, researchers have found. As Neff writes, “Far from being an excuse for self-indulgence, therefore, self-compassion pushes us forward—and for the right reasons.”

Tina Seelig, a professor of practice at Stanford University, says we also need a “failure résumé,” a detailed and thorough inventory of our flops. A failure résumé offers another method for addressing our regrets. The very act of creating one is a form of disclosure.

One place to begin is Kristin Neff’s website (https://self-compassion.org), where you can measure your own levels of self-compassion. Her book Self-Compassion: The Proven Power of Being Kind to Yourself is also excellent.

A core point of this chapter—of this entire book—is that looking backward can move us forward. One way to imprint this principle onto your life is to establish a ritual. In late December, the temporal landmark of January 1 stirs us to make New Year’s resolutions. But as a precursor to that practice, try what I call “Old Year’s regrets.”

“Live as if you were living already for the second time and as if you had acted the first time as wrongly as you are about to act now!” Viktor Frankl, 1946

If the previous two chapters were about regret through the rearview mirror, this chapter is about regret through the front windshield. Regret is a retrospective emotion. It springs into being when we look backward. But we can also use it prospectively and proactively—to gaze into the future, predict what we will regret, and then reorient our behavior based on our forecast. Sometimes that approach points us in a promising direction. Other times it can lead us astray. But if we understand both the upside and downside of anticipating regret, we can hone our strategy for pursuing the good life.

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 can 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. And together, they offer a path to the good life.

So, under the Regret Optimization Framework, when deciding a course of action, begin by asking whether you are dealing with one of the four core regrets. If not, satisfice. For example, if you’re buying lawn furniture or a(nother) microwave oven, that decision is unlikely to involve any fundamental, enduring human need. Make a choice and move on. You’ll be fine. If the decision does involve one of the big four, spend more time deliberating. Project yourself into the future—five years, ten years, at age eighty, whatever makes sense. From that future vantage point, ask yourself which choice will help you build your foundation, take a sensible risk, do the right thing, or maintain a meaningful connection. Anticipate these regrets. Then choose the option that most reduces them. Use this framework a few times, and you will begin to see its power.

If our lives are the stories we tell ourselves, regret reminds us that we have a dual role. We are both the authors and the actors. We can shape the plot but not fully. We can toss aside the script but not always. We live at the intersection of free will and circumstance.

If we think about regret like this—looking backward to move forward, seizing what we can control and putting aside what we cannot, crafting our own redemption stories—it can be liberating.