The Power of Regret: How Looking Backward Moves Us Forward

by Daniel H. Pink

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.

The purpose of this book is to reclaim regret as an indispensable emotion—and to show you how to use its many strengths to make better decisions, perform better at work and school, and bring greater meaning to your life.

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

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.

Regret is the quintessential upward counterfactual—the ultimate If Only. The source of its power, scientists are discovering, is that it muddles the conventional pain-pleasure calculus.[10] Its very purpose is to make us feel worse—because by making us feel worse today, regret helps us do better tomorrow.

A look at the research shows that regret, handled correctly, offers three broad benefits. It can sharpen our decision-making skills. It can elevate our performance on a range of tasks. And it can strengthen our sense of meaning and connectedness.

“The biggest regret is that I didn’t hear their stories,” she told me in an interview. But that has altered her approach to her own parents. Sparked by this regret, she and her siblings bought their father, who’s in his seventies, a subscription to StoryWorth. Each week the service sends an email that contains a single question (What was your mother like? What is your fondest childhood memory? And—yes—what regrets do you have?). The recipient responds with a story. At the end of the year, those stories are compiled into a hardcover book. Because of the poke of If Only, she said, “I seek out more meaning. I seek out more connection. . . . I don’t want to feel the way when my parents die that I felt about my grandparents of ‘What did I miss?’

When it comes to regret, a third view is healthier: 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.

The key is to use regret to catalyze a chain reaction: the heart signals the head, the head initiates action. All regrets aggravate. Productive regrets aggravate, then activate.

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. Forgone opportunities to leave our hometown or launch a business or chase a true love or see the world all linger in the same way.

At that juncture, we choose the path of the grasshopper. We spend too much and save too little. We drink and carouse at the expense of exercising regularly and eating right. We apply minimal and grudging effort in school, at home, or on the job. The full ramifications of these incremental choices don’t materialize immediately. But over time, they slowly accrue. Soon the full consequences become too towering to deny—and, eventually, too massive to repair.

We typically read “The Ant and the Grasshopper” as a morality tale, but it’s also a story about cognition. By partying all summer instead of gathering food for the winter, the grasshopper succumbed to what economists call “temporal discounting.”[1] He overvalued the now—and undervalued (that is, discounted) the later. When this bias grips our thinking, we often make regrettable decisions.

He explains to the associates the importance of building their skills and connections and, yes, putting aside a little from every paycheck for the future. He tells them to plan, then tries to show them how—all while attempting to heed the advice himself.

All deep structure regrets reveal a need and yield a lesson. 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.

Introversion and extroversion are not binary personality types. This trait is better understood as a spectrum—one where about two-thirds of the population lands in the middle.[1] Yet almost nobody in either the quantitative or qualitative regret surveys described excesses of extroversion, while many lamented tilting toward the other side of the scale.

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,” Gilovich and Medvec wrote in one of their early studies.[3] In my own American Regret Project survey, inaction regrets outnumbered action regrets by nearly two to one. And other research has likewise found a preponderance of inaction regrets even in less individualistic cultures, like those of China, Japan, and Russia.[4]

A key reason for this discrepancy is that when we act, we know what happened next.

For example, hundreds of people in the survey who turned down earlier opportunities to travel listed that decision as their top regret. If my regret-based dating app fails, I could instead launch an Expedia-for-the-regretful site, which would include special travel packages for the legions of college graduates in the surveys who regretted not studying abroad. “It’s not the bad or stupid things I’ve done but the things I didn’t do that have caused me the most regret in life,” said Gemma West of Adelaide, Australia. [My] biggest regret is not going backpacking around Europe when I was eighteen, because I was scared—an important rite of passage for Australians and something my best friend did with someone else. A forty-seven-year-old woman from Utah said: I regret not traveling more when I was younger—before I had a mortgage and child and “real job” and all the responsibilities of being an adult. Because now, I don’t feel like I have the freedom to do it.

Boldness regrets, as with the Ohio man above, are often about exploration. And some of the most significant exploration, respondents said, is inward. Authenticity requires boldness. And when authenticity is thwarted, so is growth. The most telling demonstration of this point came from several dozen people from all over the world who described their regret—their failure to be bold—with the same five words: “Not being true to myself.”

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.

But you and I and our nearly eight billion fellow humans don’t share a single definition of what it means to be “moral.”

First, I’d long believed that when we face morally weighty questions (Is the death penalty justified? Should assisted suicide be legal?), we reason through the issues to arrive at a conclusion. We approach these questions like a judge who evaluates competing arguments, ponders both sides, and delivers a reasoned decision. But according to Haidt’s research, that simply isn’t accurate. Instead, when we consider what’s moral, we have an instantaneous, visceral, emotional response about right or wrong—and then we use reason to justify that intuition.[2] 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.

Haidt and his colleagues call this idea “moral foundations theory.”

On this, too, most people in most cultures agree: we should tell the truth, keep our promises, and play by the agreed-upon rules.

All deep structure regrets reveal a need and yield a lesson. With moral regrets, the need is goodness. The lesson, which we’ve heard in religious texts, philosophy tracts, and parental admonitions, is this: when in doubt, do the right thing.

As the Harvard Gazette summarized in 2017: 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.[7] Men who’d had warm childhood relationships with their parents earned more as adults than men whose parent-child bonds were more strained. They were also happier and less likely to suffer dementia in old age. People with strong marriages suffered less physical pain and emotional distress over the course of their lives. Individuals’ close friendships were more accurate predictors of healthy aging than their cholesterol levels. Social support and connections to a community helped insulate people against disease and depression. Meanwhile, loneliness and disconnection, in some cases, were fatal.

Reltionships are key…