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.

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

“Regret is created by a comparison between the actual outcome and that outcome that would have occurred had the decision maker made a different choice,”

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.

“Counterfactuals are . . . a signature example of the imagination and creativity that stand at the intersection of thinking and feeling,” say Neal Roese of Northwestern University and Kai Epstude of the University of Groningen, two leading scholars of the subject.[1] Counterfactuals permit us to imagine what might have been.

Lingering on a regret for too long, or replaying the failure over and over in your head, can have the opposite effect. Selecting the wrong target for your regret—say, that you wore a red baseball cap at the blackjack table rather than that you took another card when you were holding a ten and a king—offers no improvement. And sometimes the initial pain can momentarily throw us. But most times, reflecting even a bit on how we might benefit from a regret boosts our subsequent showing.[14]

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.[27]

framing regret as a judgment of our underlying character—who we are—can be destructive. Framing it as an evaluation of a particular behavior in a particular situation—what we did—can be instructive.

“If you have a broken heart, it means you have done something big enough and important enough and valuable enough to have broken your heart.”

Boldness regrets. A stable platform for our lives is necessary, but not sufficient. One of the most robust findings, in the academic research and my own, is that over time we are much more likely to regret the chances we didn’t take than the chances we did. Again, the surface domain—whether the risk involved our education, our work, or our love lives—doesn’t matter much. What haunts us is the inaction itself.

Connection regrets. Our actions give our lives direction. But other people give those lives purpose. A massive number of human regrets stem from our failure to recognize and honor this principle. Fractured or unrealized relationships with spouses, partners, parents, children, siblings, friends, classmates, and colleagues constitute the largest deep structure category of regret. Connection regrets arise any time we neglect the people who help establish our own sense of wholeness. When those relationships fray or disappear or never develop, we feel an abiding loss.

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.

Foundation regrets are trickier than the other three deep structure regrets I’ll describe in upcoming chapters. Remember that what distinguishes regret from disappointment is personal responsibility.

With this category of regrets, something similar might be happening—a foundation attribution error. We attribute these failures, in ourselves and others, to personal choices when they’re often at least partly the result of circumstances we can’t control.[*] That means that the fix for foundation regrets, and a way to avoid them, is not only to change the person, but to reconfigure that person’s situation, setting, and environment. We must create the conditions at every level—society, community, and family—to improve individuals’ foundational choices.

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. Sometimes boldness regrets emerge from an accumulation of decisions and indecisions; other times they erupt from a single moment. But whatever their origin, the question they present us is always the same: Play it safe or take a chance?

With boldness regrets, we choose to play it safe. That may relieve us at first. The change we’re contemplating may sound too big, too disruptive, too challenging—too hard. But eventually the choice distresses us with a counterfactual in which we were more daring and, consequently, more fulfilled. Boldness regrets sound like this: If only I’d taken that risk.

The pain of boldness regrets is the pain of “What if?” Thomas Gilovich, Victoria Medvec, and other researchers have repeatedly found that people regret inactions more than actions—especially in the long term. “Regrettable failures to act . . . have a longer half-life than regrettable actions,”

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. “Because regrettable inactions are more alive, current, and incomplete than are regrettable actions, we are reminded of them more often,”

It is the sin of omission, the second kind of sin, That lays eggs under your skin.[6]

The consequences of actions are specific, concrete, and limited. The consequences of inaction are general, abstract, and unbounded. Inactions, by laying eggs under our skin, incubate endless speculation.

Boldness regrets endure because the counterfactual possibilities are so vast.

At the heart of all boldness regrets is the thwarted possibility of growth. The failure to become the person—happier, braver, more evolved—one could have been. The failure to accomplish a few important goals within the limited span of a single life.

All deep structure regrets reveal a need and yield a lesson. With boldness regrets, the human need is growth—to expand as a person, to enjoy the richness of the world, to experience more than an ordinary life.

The lesson is plain: Speak up. Ask him out. Take that trip. Start that business. Step off the train.

“We didn’t have a falling out of any kind. I just let it kind of drift away,” Cheryl told me. “I regret not having that relationship in my life. I’ve missed having another person in my life who could share with me the kind of growth I’ve experienced over the years.”

The absence disquiets her. “If you’re going to die in a month, are there things you would want tied up?” Cheryl said. “I would like her to know that [the friendship] feels significant to me even twenty-five years later.”

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 relationship that was once intact, or that ought to have been intact, no longer is. Sometimes, often because of a death, there is nothing more that we can do. However, many times, in many roles—daughter, uncle, sorority sister—we yearn to close the circle. But doing so requires effort, brings emotional uncertainty, and risks rejection. So we confront a choice: Try to make the relationship whole—or let it remain unresolved? Connection regrets sound like this: If only I’d reached out.

Reason, regret, reason, regret, reason, regret play ping-pong in my brain whenever I think about that event from fifteen years ago.

regrets about social relationships are felt more deeply than other types of regrets because they threaten our sense of belonging. When our connections to others tatter or disintegrate, we suffer. And when it’s our fault, we suffer even more. “The need to belong,” they wrote, “is not just a fundamental human motive but a fundamental component of regret.”[2]

While the connection regrets that people reported in the surveys numbered well into the thousands, the specific ways their relationships ended numbered only two: rifts and drifts. Rifts usually begin with a catalyzing incident—an insult, a disclosure, a betrayal. That incident leads to raised voices, ominous threats, crashed plates, and other mainstays of telenovelas and Edward Albee plays. Rifts leave the parties resentful and antagonistic, even though to outsiders the underlying grievance might sound trivial and easy to repair.

Drifts follow a muddier narrative. They often lack a discernible beginning, middle, or end. They happen almost imperceptibly. One day, the connection exists. Another day, we look up, and it’s gone.

Rifts are more dramatic. But drifts are more common. Drifts can also be harder to mend. Rifts generate emotions like anger and jealousy, which are familiar and easier to identify and comprehend. Drifts involve emotions that are subtler and that can feel less legitimate. And first among these emotions, described by hundreds of people with connection regrets, is awkwardness.

“Taking care of your body is important, but tending to your relationships is a form of self-care too. That, I think, is the revelation.”[8]

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.

“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.”

All deep structure regrets reveal a need and yield a lesson. With connection regrets, the human need is love. Not love only in the romantic sense—but a broader version of love that includes attachment, devotion, and community and that encompasses parents, children, siblings, and friends.

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] What fuels our behavior and directs which goals we pursue, Higgins argued, are discrepancies between these three selves.

people regret their failures to live up to their ideal selves more than their failures to live up to their ought selves. Regrets of “coulda” outnumbered regrets of “shoulda” by about three to one.

Discrepancies between our actual self and our ideal self leave us dejected. But discrepancies between our actual self and our ought self make us agitated—and therefore more likely to act. We feel a greater sense of urgency about ought-related regrets, so we’re more likely to begin repair work—by undoing past behavior, apologizing to those we’ve wronged, or learning from our mistakes.[2] “Couldas” bug us longer than “shouldas,” because we end up fixing many of the “shouldas.”[*]

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.

For example, boldness regrets—If only I’d taken that risk—are entirely about opportunities we didn’t seize.[3] Foundation regrets—If only I’d done the work—are also largely about opportunities (for education, health, financial well-being) that we didn’t pursue. Connection regrets—If only I’d reached out—are a mix. They involve opportunities for friendship we didn’t follow through on, as well as obligations to family members and others that we neglected. Moral regrets—If only I’d done the right thing—are about obligations we didn’t meet.

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.

For action regrets, your initial goal should be to change the immediate situation for the better. That’s not always possible, but we have two ways to advance toward that goal. We can undo many such regrets: we can make amends, reverse our choices, or erase the consequences.

action regrets typically arise from concrete incidents and elicit “hot” emotions that we respond to quickly. Inaction regrets, by contrast, are often more abstract and elicit less immediately intense emotions. What’s more, many inaction regrets are inherently difficult to undo.

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?

If the action regret can be undone, try to do that—even if a light physical or metaphysical bruise remains. But if it can’t be undone, fear not. You’ve got another possibility.

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.