The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

Connection regrets are the largest category in the deep structure of human regret. They arise from relationships that have come undone or that remain incomplete. The types of relationships that produce these regrets vary. Spouses. Partners. Parents. Children. Siblings. Friends. Colleagues. The nature of the rupture also varies. Some relationships fray. Others rip. A few were inadequately stitched from the beginning.

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.

Regret works much the same way. The four core regrets operate as a photographic negative of the good life. If we know what people regret the most, we can reverse that image to reveal what they value the most.

THE DEEP STRUCTURE OF REGRET

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]

Failures to become our ideal selves are failures to pursue opportunities. Failures to become our ought selves are failures to fulfill obligations. All four of the core regrets involve opportunity, obligation, or both.

“Regrets of inaction last longer than regrets of action in part because they reflect greater perceived opportunity.”

By age fifty, inaction regrets were twice as common as action regrets. Indeed, according to the data, age was by far the strongest predictor of regrets of inaction.

We regret foregone opportunities more often than unfulfilled obligations. Yet we also know that a wholly realized life involves a mix of both dreams and duties.[5] The photographic negative that regret offers makes clear that being fully human combines our dreams for ourselves and our duties to others. A life of obligation and no opportunity is crimped. A life of opportunity and no obligation is hollow. A life that fuses opportunity and obligation is true.

So, to address regrets of action, begin by asking yourself these questions: If I’ve harmed others, as is often the case with moral regrets and sometimes the case with connection regrets, can I make amends through an apology or some form of emotional or material restitution? If I’ve harmed myself, as is the case for many foundation regrets and some connection regrets, can I fix the mistake? For example, can I begin paying down debt or logging a few more hours at work? Can I reach out immediately to someone whose connection I severed?

At Leasts can turn regret into relief.

So, with action regrets that are bringing you down, ask yourself: How could the decision I now regret have turned out worse? What is one silver lining in this regret? How would I complete the following sentence? “At least . . .”

Self-disclosure is intrinsically rewarding and extrinsically valuable. It can lighten our burden, make abstract negative emotions more concrete, and build affiliation. So, to begin to harness your regrets to improve in the future, try any of the following: Write about your regret for fifteen minutes for three consecutive days. Talk about your regret into a voice recorder for fifteen minutes for three consecutive days. Tell someone else about the regret in person or by phone. Include sufficient detail about what happened, but establish a time limit (perhaps a half hour) to avoid the possibilities of repetition and brooding.

Self-criticism can sometimes motivate our performance when we criticize ourselves for particular actions rather than for deep-seated tendencies. But unless carefully managed and contained, self-criticism can become a form of inner-directed virtue signaling. It projects toughness and ambition, but often leads to rumination and hopelessness instead of productive action.[12]

self-esteem measures how much you value yourself. How good do you feel about who you are?

But self-esteem brings downsides. Because it offers indiscriminate affirmation unconnected to genuine accomplishment, self-esteem can foster narcissism, diminish empathy, and stoke aggression.

Because self-esteem is comparative, to assess myself favorably, I often must denigrate others.

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.

In a sense, self-compassion delivers the benefits of self-esteem without its drawbacks.

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.

So, to gain the benefits of self-distancing, try any of the following: 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?

SEVEN OTHER TECHNIQUES YOU WON’T REGRET

1. Start a regret circle.

2. Create a failure résumé.

3. Study self-compassion.

4. Pair New Year’s resolutions with Old Year’s regrets.

5. Mentally subtract positive events.

6. Participate in the World Regret Survey.

7. Adopt a journey mindset.

Regret lotteries are one way that anticipated regrets can alter our behavior. With an ordinary lottery, I must take affirmative steps to enter—in the Duke example, by filling out the questionnaire and returning it. If I don’t do that and someone who does ends up winning, I might be slightly bummed out (assuming I even find out). But with the odds slim and my emotional investment almost nonexistent, I’m unlikely to be devastated.

Anticipating regret offers a convenient tool for judgment. In situations where you’re unsure of your next move, ask yourself, “In the future, will I regret this decision if I don’t do X?” Answer the question. Apply that answer to your current situation. This approach underlies the (small but growing) popularity of “obituary parties”—in which people channel their inner Alfred Nobel, draft their own obits, and use the written pieces to inform their remaining years.[20] It is also the animating idea of “pre-mortems.” In this management technique, work teams mentally travel to the future before a project even begins to imagine a nightmare scenario where everything went wrong—say, the project came in over time or over budget or didn’t even get done. Then they use those insights to avoid the blunders before they occur.[21]

Jeff Bezos. He’s one of the richest people in the world, thanks to founding Amazon, one of the largest companies on the planet. He owns The Washington Post. He visits outer space. Yet in the domain of our most misunderstood emotion, he is best known for a concept that he calls the “Regret Minimization Framework.”

Overestimating regret has another consequence: it can cloud our decisions.

Anticipating regret can sometimes steer us away from the best decision and toward the decision that most shields us from regret—as

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.

Our goal should not be to always minimize regret. Our goal should be to optimize it. By combining the science of anticipated regret with the new deep structure of regret, we can refine our mental model. 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.

WHAT TO DO WITH YOUR REGRETS: A RECAP For an Action Regret Undo it. Apologize, make amends, or try to repair the damage. At Least It. Find the silver lining: think about how the situation could have turned out worse and appreciate that it didn’t. For Any Regret (Action or Inaction) Self-disclosure. Relive and relieve the regret by telling others about it—admission clears the air—or by writing about it privately. Self-compassion. Normalize and neutralize the regret by treating yourself the way you’d treat a friend. Self-distancing. Analyze and strategize about the lessons you’ve learned from the regret by zooming out in time, in space, or through language. To Use Anticipated Regrets in Your Decision Making: Satisfice on most decisions. If you are not dealing with one of the four core regrets, make a choice, don’t second-guess yourself, and move on. Maximize on the most crucial decisions. If you are dealing with one of the four core regrets, project yourself to a specific point in the future and ask yourself which choice will most help you build a solid foundation, take a sensible risk, do the right thing, or connect with others.

Just 5 percent of the sample disagreed with both propositions. Those people said they didn’t have free will and that things didn’t happen for a reason. Call this tiny cohort the nihilists. Meanwhile, 10 percent believed they exercised free will while rejecting the idea that events unfold for a purpose. Call this group the individualists. Another 10 percent held the reverse view. Free will was a myth and everything happened for a reason, they said. These are the fatalists. But the largest group by far—three out of four Americans in the survey—maintained both that they have free will and that most things happen for a reason, two beliefs that seem to contradict each other. What to call this mystifying group? I thought about it awhile. And after careful consideration, the name I’ve chosen to assign them is . . . the humans.

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

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] McAdams has found that people whose identities involve contamination narratives tend to be unhappy with their personal lives and unimpressive in their professional contributions. But people with narratives rooted in redemption are the opposite. They are generally more satisfied and accomplished—and they rate their lives as meaningful. Regret offers us the ultimate redemption narrative. It is as powerful and affirming as any positive emotion. But it arrives on our doorstep wearing a disguise.