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.

These seventy years of research distill to two simple yet urgent conclusions: Regret makes us human. Regret makes us better.

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.

This is one of the central findings on regret: it can deepen persistence, which almost always elevates performance.

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.[27]

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.

When feeling is for thinking, and thinking is for doing, regret is for making us better.

“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.”

It took me a while to figure out, but I’ve discovered that regret, too, has both a surface structure and a deep structure. What’s visible and easy to describe—the realms of life such as family, education, and work—is far less significant than a hidden architecture of human motivation and aspiration that lies beneath it.

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. Our lives require some basic level of stability. Without a measure of physical well-being and material security, other goals become difficult to imagine and even harder to pursue.

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.

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

Fractured or unrealized relationships with spouses, partners, parents, children, siblings, friends, classmates, and colleagues constitute the largest deep structure category of regret.

Foundation regrets arise from our failures of foresight and conscientiousness. Like all deep structure regrets, they start with a choice.

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

Foundation regrets begin with an irresistible lure and end with an inexorable logic.

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.

To identify a foundation regret in yourself or in others, listen for the words “too much”—whether they attach to consuming alcohol, playing video games, watching television, spending money, or any other activity whose immediate lure exceeds its lasting value. Then listen for the words “too little”—whether they describe studying in school, setting aside cash, practicing a sport or musical instrument, or any other undertaking that requires steady commitment.

Foundation regrets are not just difficult to avoid. They are also difficult to undo.

One of the most prevalent cognitive biases—in some ways the über-bias—is called the “fundamental attribution error.” When people, especially Westerners, try to explain someone’s behavior, we too often attribute the behavior to the person’s personality and disposition rather than to the person’s situation and context.[5]

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.

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.

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.

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

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.

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

Haidt and his colleagues call this idea “moral foundations theory.” [4] Drawing on evolutionary biology, cultural psychology, and several other fields, they show that beliefs about morality stand on five pillars:

Care/harm:

Those who nurture and defend the vulnerable are kind; those who hurt them are cruel.

Fairness/cheating:

That means we value those whom we can trust and disdain those who breach our trust.

Loyalty/disloyalty:

being true to your team, sect, or nation is respected—and forsaking your tribe is usually reviled.

Authority/subversion:

Those who undermine the hierarchy can place everyone in the group at risk. When this evolutionary impulse extends to human morality, traits like deference and obedience toward those at the top become virtues.

Purity/desecration:

In the moral realm, write one set of scholars, “purity concerns uniquely predict (beyond other foundations and demographics such as political ideology) culture-war attitudes about gay marriage, euthanasia, abortion, and pornography.”

THE FIVE REGRETTED SINS

Harm

People of all political persuasions agree: hurting someone who’s not provoking us is wrong.

Unlike boldness regrets, moral regrets are more likely to involve actions than inactions.

Cheating

Regrets about hurting others, especially through bullying, were the most pervasive. But regrets about cheating, especially in marriages, finished a close second. On this, too, most people in most cultures agree: we should tell the truth, keep our promises, and play by the agreed-upon rules.

Disloyalty

Loyalty to a group is a core moral value. It’s expressed with greater gusto in some political and national cultures than in others. And perhaps because of that, regrets about this moral foundation were not as numerous as those about harm and cheating.

As Haidt writes in The Righteous Mind, the moral foundation of loyalty helps groups cement bonds and form coalitions. It shows “who is a team player and who is a traitor, particularly when your team is fighting with other teams.” [8]