The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

most children don’t begin to understand regret until age six.[6] But by age eight, they develop the ability even to anticipate regret.[7] And by adolescence, the thinking skills necessary to experience regret have fully emerged.[8] Regret is a marker of a healthy, maturing mind.

Comparison lives at regret’s core.

the capacity for regret might be a fundamental part of how our sons and daughters learn to reason and make decisions themselves.

“The development of regret allows children to learn from previous decisions in order to adaptively switch their choices,”

Blocked emotions, writes one therapist, can even lead to “physical problems like heart disease, intestinal problems, headaches, insomnia and autoimmune disorders.”[22]

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]

What do people regret? Lots of stuff. Why do they have those regrets? Something about opportunity.

Education is still third. Romance after Tinder could help explain the skew. Availability bias. When you look at the top three (or four with career tied for third), you may see the American dilemma that universities are confronting and high schools are culturing. Do we give students opportunities for "if only" applied to educational and career choices or only "at least" for families and romance?

Nearly 22 percent of respondents voiced a regret in this category, followed closely by the 19 percent whose regret involved partners. Running just behind, and bunched together tightly, were education,

Education is still third and my guess is that education is the key to helping the first two (families and partners). Maybe there is a launch here: third places and education?

Many of our education, finance, and health regrets are actually different outward expressions of the same core regret: our failure to be responsible, conscientious, or prudent.

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.

When we behave poorly, or compromise our belief in our own goodness, regret can build and then persist.

Foundation regrets sound like this: If only I’d done the work.

Many individual health, education, or financial missteps are not themselves immediately devastating. But the slowly building force of all those poor decisions can arrive like a tornado—gradually and then suddenly. By the time we realize what’s happening, there’s not much we can do.

With foundation regrets, the human need it lays bare is stability: we all require a basic infrastructure of educational, financial, and physical well-being that reduces psychological uncertainty and frees time and mental energy to pursue opportunity and meaning.

Boldness regrets sound like this: If only I’d taken that risk.

Moral regrets sound like this: If only I’d done the right thing.

The rational mind isn’t a black-robed jurist rendering unbiased pronouncements, as I’d thought. It’s the press secretary for our intuitions. Its job is to defend the boss.

Connection regrets sound like this: If only I’d reached out.

Commuters feared that reaching out would be uncomfortable for everyone, but their fears were misplaced. It wasn’t awkward at all.

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.

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.

A solid foundation. A little boldness. Basic morality. Meaningful connections. The negative emotion of regret reveals the positive path for living.

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.

“Couldas” bug us longer than “shouldas,” because we end up fixing many of the “shouldas.”[*]

The result is that opportunity and obligation sit at the center of regret, but opportunity has the more prominent seat. This also helps explain why we’re more likely to regret what we didn’t do than what we did.

A life that fuses opportunity and obligation is true.

Apologies, wrote the great sociologist Erving Goffman, are “admissions of blameworthiness and regret for an undesirable event that allow actors to try to obtain a pardon from audiences.”[2] If that pardon is granted, the emotional and moral debt of the past is reduced, which at least partially rebalances the ledger.

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.

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]

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.

After administering their Maximization Scale to more than 1,700 participants, they connected the results to measures of these participants’ well-being. And the researchers uncovered a surprise. Most maximizers were miserable. The maximizers reported “significantly less life satisfaction, happiness, [and] optimism” and significantly more depression than the satisficers.[34]

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]

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. But anticipating regrets outside these four categories is usually not worthwhile.

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.

If we know what we truly regret, we know what we truly value.

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.

But people with narratives rooted in redemption are the opposite. They are generally more satisfied and accomplished—and they rate their lives as meaningful.

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.