The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

A fifty-four-year-old woman shared this: I regret not being nicer to my mom. I took her for granted when I was younger, thinking that I was so much smarter than she was (typical teenager). When I grew up, we argued over politics, both of us passionate about our viewpoints. Now that she is gone, I miss her desperately, so much that it takes my breath away sometimes. I did the daughter thing all wrong. I look at my daughters and pray that they are kinder to me than I was to my own mom, even though I’m not sure I deserve it.

“There was a sort of awkwardness to me of ‘I haven’t really talked to you in years. But, hey, I heard you’re dying and I’m going to call!’ ” Amy explained. “I wish I had not been afraid to confront the uncomfortable feelings I knew I was going to have when I called her.”

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.

“You’re almost always better off to err on the side of showing up. And if it’s awkward, then it’s awkward and you’ll live. It’ll be fine. But if you don’t show up, it’s lost forever.”

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.

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 . . .”

In this research, writing about negative experiences like regret, and even talking into a tape recorder about them, for fifteen minutes a day substantially increased people’s overall life satisfaction and improved their physical and mental well-being in ways that merely thinking about those experiences did not.

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.[7]

But the evidence shows that self-disclosure builds affinity much more often than it triggers judgment. One major review of the literature concluded that “people who engage in intimate disclosures tend to be liked more than people who disclose at lower levels.”

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-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.”

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.

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.

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.

Self-distancing changes your role from scuba diver to oceanographer, from swimming in the murky depths of regret to piloting above the water to examine its shape and shoreline. “People who self-distance focus less on recounting their experiences and more on reconstruing them in ways that provide insight and closure,”

First, we can distance through space. The classic move is known, unsurprisingly, as the “fly-on-the-wall technique.” Rather than examine your regret from your own perspective—“I really screwed up by letting my close friendship with Jen come apart and then doing nothing to fix it”—view the scene from the perspective of a neutral observer. “I watched a person let an important friendship drift. But all of us make mistakes, and she can redeem this one by reaching out to meaningful connections, including Jen, more regularly and more often.”

the fly-on-the-wall technique helps us withstand and learn from criticism—it makes it easier not to take it personally—which is essential in transforming regrets into instruments for improvement.

The second way to self-distance is through time. We can enlist the same capacity for time travel that gives birth to regret to analyze and strategize about learning from these regrets. For example, one study showed that prompting people to consider how they might feel about a negative situation in ten years reduced their stress and enhanced their problem-solving capabilities compared to contemplating what the situation would be like in a week.

Kross, Ayduk, and others have carried out some fascinating research concluding that “subtle shifts in the language people use to refer to themselves during introspection can influence their capacity to regulate how they think, feel, and behave under stress.” [40] When we abandon the first person in talking to ourselves, the distance that creates can help us recast threats as challenges and replace distress with meaning.

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?

Looking backward can move us forward, but only if we do it right. The sequence of self-disclosure, self-compassion, and self-distancing offers a simple yet systematic way to transform regret into a powerful force for stability, achievement, and purpose.

A few years ago, I compiled a failure résumé, then tried to glean lessons from the many screwups I’d committed. (Disclosing these embarrassments to myself will be sufficient, thank you very much.) I realized I’d repeatedly made variations of the same two mistakes, and that knowledge has helped me avoid those mistakes again.

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.

Clarence’s technique is called “mentally subtracting positive events.” [47] Think of something good in your life—a close friendship, a career achievement, one of your children. Consider all the decisions and indecisions, mistakes and triumphs, that led to that happy situation. Now take them away. To use an example from the last chapter, I could mentally subtract having met my wife. The result is misery and gloom. But, as happened with George Bailey, the subtraction deepens my gratitude and casts my regrets in a new light.

If you haven’t done so already, submit your regret to the World Regret Survey (www.worldregretsurvey.com). Putting your regret in writing can defang it—and can offer the distance to evaluate it and plan from it. You can also read other people’s regrets, which provides perspective on our shared humanity and can help strengthen your regret-reckoning muscles.

As you read regrets from across the globe, ask yourself: What kind of regret is this? What advice would you give the writer for using her regret as a positive force?

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. One antidote to this problem comes from the work of Stanford University professors Szu-chi Huang and Jennifer Aaker, who recommend what they call a “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.

“I regret wasting so much free time before having children. In hindsight, I absolutely WAS NOT too busy to learn Spanish, exercise regularly, or put in extra effort at work to attain mastery.” Male, 29, Indiana

“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

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.

One problem with using anticipated regrets as a decision-making tool is that we’re pretty bad at predicting the intensity and duration of our emotions.[23] And we’re particularly inept at predicting regret. We often overestimate how negative we’ll feel and underestimate our capacity to cope or balm our feelings with At Leasts.

anticipated regret “can be a bit of a boogeyman, looking larger in prospect than it actually stands in experience.”

They became less concerned with making the smarter choice and tried to make the less regrettable choice—and those aren’t always the same.

When the scientists tried to explain the source of the unhappiness, they identified the main culprit: “maximizers’ increased sensitivity to regret—both experienced and anticipated.” 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.

literally me

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.

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

The Regret Optimization Framework holds that we should devote time and effort to anticipate the four core regrets: foundation regrets, boldness regrets, moral regrets, and connection regrets.