The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

Finding a silver lining doesn’t negate the existence of a cloud. But it does offer another perspective on that cloud.

Hers is a regret of inaction, so she can’t undo it; it’s not possible to reverse a twenty-five-year void. She can’t At Least it either. Saying “Our friendship evaporated, but at least we didn’t have a huge fight” doesn’t offer much solace or meaningfully adjust the present. Cheryl’s best response—and the optimal response to most regrets, action and inaction alike—is to use the regret to improve the future. If we look backward with the specific intent of moving forward, we can convert our regrets into fuel for progress. They can propel us toward smarter choices, higher performance, and greater meaning. And science shows us how.

Rather than ignoring the negative emotion of regret—or worse, wallowing in it—we can remember that feeling is for thinking and that thinking is for doing. Following a straightforward three-step process, we can disclose the regret, reframe the way we view it and ourselves, and extract a lesson from the experience to remake our subsequent decisions.

The first step in reckoning with all regrets, whether regrets of action or inaction, is self-disclosure. We’re often skittish about revealing to others negative information about ourselves. It feels awkward, even shameful. But an enormous body of literature makes clear that disclosing our thoughts, feelings, and actions—by telling others or simply by writing about them—brings an array of physical, mental, and professional benefits. Such self-revelation is linked to reduced blood pressure, higher grades, better coping skills, and more.[4] Indeed, Tamir and Mitchell maintain that “our species may have an intrinsic drive to disclose thoughts to others.”[5]

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 of it.

The most powerful and promising alternative—and the second step in the regret-reckoning process—was pioneered nearly twenty years ago by University of Texas psychologist Kristin Neff. It is called “self-compassion.”

Self-compassion begins by replacing searing judgment with basic kindness. It doesn’t ignore our screwups or neglect our weaknesses. It simply recognizes that “being imperfect, making mistakes, and encountering life difficulties is part of the shared human experience.”[15]

By normalizing negative experiences, we neutralize them. Self-compassion encourages us to take the middle road in handling negative emotions—not suppressing them, but not exaggerating or overidentifying with them either.

self-compassion delivers the benefits of self-esteem without its drawbacks. It can insulate us from the debilitating consequences of self-criticism, while short-circuiting self-esteem’s need to feel good through vanity and comparison.

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.”[28] So, drawing on the science of self-compassion, the second step in transforming our regrets is to ask ourselves three questions: If a friend or relative came to you with the same regret as yours, would you treat that person with kindness or contempt? If your answer is kindness, use that approach on yourself. If your answer is contempt, try a different answer. Is this type of regret something that other people might have endured, or are you the only person ever to have experienced it? If you believe your stumble is part of our common humanity, reflect on that belief, as it’s almost always true. If you believe the world has it out for you alone, please reread Chapters 7–10. Does this regret represent an unpleasant moment in your life, or does it define your life? Again, if you believe it’s worth being aware of the regret but not overidentifying with it, you’re on your way. If you believe this regret fully constitutes who you are, ask someone else what they think. These three questions, which form the hea...

When we’re beset by negative emotions, including regret, one response is to immerse ourselves in them, to face the negativity by getting up close and personal. But immersion can catch us in an undertow of rumination. A better, more effective, and longer-lasting approach is to move in the opposite direction—not to plunge in, but to zoom out and gaze upon our situation as a detached observer, much as a movie director pulls back the camera.

After self-disclosure relieves the burden of carrying a regret, and self-compassion reframes the regret as a human imperfection rather than an incapacitating flaw, self-distancing helps you analyze and strategize—to examine the regret dispassionately without shame or rancor and to extract from it a lesson that can guide your future behavior.

Imagine your best friend is confronting the same regret that you’re dealing with. What is the lesson that the regret teaches them? What would you tell them to do next? Be as specific as you can. Now follow your own advice. Imagine that you are a neutral expert—a doctor of regret sciences—analyzing your regret in a clean, pristine examination room. What is your diagnosis? Explain in clinical terms what went wrong. Next, what is your prescription? Now write an email to yourself—using your first name and the pronoun “you”—outlining the small steps you need to learn from the regret. If your regret involves your business or career, try a technique from the late Intel CEO Andy Grove, who reportedly would ask himself, “If I were replaced tomorrow, what would my successor do?” [46] Imagine it is ten years from now and you’re looking back with pride on how you responded to this regret. What did you do?

Pair New Year’s resolutions with Old Year’s regrets. 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.” Look back on the year that’s about to end and list three regrets. Do you regret not reconnecting with a relative or former colleague? Or never getting around to launching that side business? Or telling a lie that compromised your values? Write down these regrets. And make undoing the action regrets and transforming the inaction regrets your top resolutions for the new year.

Adopt a journey mindset. Achieving our goals can insulate us from regret. But if we don’t sustain our behavior after reaching those goals—by continuing to exercise regularly or by maintaining the good work habits that led to the completion of a project—regret quickly finds its way into our minds.

“journey mindset.” Huang and Aaker have found that when we reach a destination—when we’ve completed a difficult and important task—we sometimes slack off and assume our work is done. But it’s usually not. Don’t just relish the goal you’ve achieved. Review the steps that got you there. Spend less time celebrating the destination and more time contemplating the journey.

minimizing regret is not the same as minimizing risk. And if we don’t anticipate properly, we end up making the regret-minimizing choice rather than the risk-minimizing choice. Sometimes that means no decision at all. Regret aversion can often lead to decision aversion, many studies have shown.[28] If we focus too much on what we’ll regret, we can freeze and decide not to decide. Likewise, in studies of negotiation, focusing too much on anticipated regret actually stalled progress. It made negotiators risk averse and less likely to strike a deal.[29]

Anticipated regret—AR—can often make us better. But as your eventful day demonstrates, before you take this medicine, read the label. Warning: AR may cause decision paralysis, risk aversion, first instinct fallacies, and lower test scores. As a universal drug, anticipated regret has a few dangerous side effects. But that’s not its only problem.

Maximizers regretted everything at every stage. Before they made their choices. After they made their choices. While they made their choices. Whatever the situation, they always imagined the possibilities of something better if only they had acted differently.[35] But these upward counterfactuals didn’t uncork productive “feeling is for thinking” regret. They trapped people in ruminating “feeling is for feeling” regret. In their effort to maximize happiness on all things, they were pulverizing it on most things. And herein lies a problem. The wobbly beam in Bezos’s Regret Minimization Framework is that constantly trying to anticipate and minimize our regrets can become a form of unhealthy maximizing. Applying this framework at all times and in all realms is a recipe for despair. How, then, to reconcile these countervailing currents—to gain the benefits of anticipated regret without becoming caught in its downdraft? The solution is to focus our aspirations.

Our goal should not be to always minimize regret. Our goal should be to optimize it.

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.

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.

Open the hood of regret, and you’ll see that the engine powering it is storytelling. Our very ability to experience regret depends on our imagination’s capacity to travel backward in time, rewrite events, and fashion a happier ending than in the original draft. Our capacity to respond to regret, to mobilize it for good, depends on our narrative skills—disclosing the tale, analyzing its components, and crafting and recrafting the next chapter.

Regret depends on storytelling. And that raises a question: In these stories, are we the creator or the character, the playwright or the performer?

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.

According to his research, two prototypical narratives wrestle for primacy as we make sense of our existence. One is what he calls “contamination sequences”—in which events go from good to bad. The other he calls “redemption sequences”—in which events go from bad to good.[1]

Regret makes me human. Regret makes me better. Regret gives me hope.