The Power of Regret: How Looking Backward Moves Us Forward

“Or take our far-flung tattooed tribe. Talk with them just a little and it’s clear that the outer expression of ‘No regrets’—the performance—and the inner experience diverge.”

Pink suggests that people who get tattoos that embrace the “No regrets” philosophy do have regrets and acknowledge them. He frames the philosophy as a performance that embraces toxic positivity, while regret is a natural human emotion that people experience despite performative claims to the contrary.

“About one of every five people who get tattoos (presumably including people whose tattoos read ‘No regrets’) eventually regret their decision, which is why the tattoo removal business is a $100 million-a-year industry in the United States alone.”

Pink points out the irony that even people who embrace the “No regrets” philosophy by getting tattoos that read “No regrets” eventually regret the decision. He also highlights the universality of personal growth and the role that regret plays in it. The volume of people who eventually remove their tattoos reveals that people “grow out of” some decisions and seek to reverse decisions if possible.

“Heeding others’ advice and our own intuitions, we stuff our portfolios with positive emotions and sell off the negative ones. But this approach to emotions—to jettison the negative and pile on the positive—is as misguided as the approach to investing that prevailed before modern portfolio theory.”

Pink suggests that just as people should diversify their stock portfolios, they should embrace the diversity of emotions we experience and value the negative as well as the positive. After all, negative emotions catalyze positive change.

“You and I and our upright, bipedal, large-brained sisters and brothers wouldn’t be here today if we lacked the capacity, occasionally but systematically, to feel bad.”

Pink subverts self-help strategies that focus solely on positivity by pointing out the importance of having a variety of emotions—both good and bad. He suggests that negative emotions help people not only survive but evolve.

“We can visit the past and the future in our heads. And we can tell the story of something that never actually happened. Human beings are both seasoned time travelers and skilled fabulists. These two capabilities twine together to form the cognitive double helix that gives life to regret.”

Pink points out that regret is linked to counterfactual thinking—our ability to consider the past and imagine hypothetical situations and outcomes linked to decisions we could have made. What makes regret so universal is its ties to humans’ imagination and talent for storytelling.

“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.”

Pink points out that counterfactual thinking is what leads people to experience regret. A negative emotion linked to a past decision becomes regret when we compare the decision and outcome to a better decision and outcome. Because of this link, it seems the purpose of regret is to get us to think about our decisions and determine how to make better decisions going forward.

“Every damn thing you do in life can pay off for you.”

Pink revises French singer Edith Piaf’s last words, “Every damn thing you do in this life you have to pay for” (26). Although Piaf had championed the adage “No regrets” in one of her popular songs, she died with regrets that went unacknowledged. Pink writes the antithesis to Piaf’s last words, suggesting that even regrets can “pay off” when people acknowledge them and consider the ways they can improve their lives.

“Two decades of counterfactual thinking exposes an oddity: thoughts about the past that make us feel better are relatively rare, while thoughts that make us feel worse are exceedingly common [...] [W]e are organisms programmed for survival. At Least counterfactuals preserve our feelings in the moment, but they rarely enhance our decisions or performance in the future. If Only counterfactuals degrade our feelings now, but—and this is key—they can improve our lives later.”

Pink attributes our tendency to experience more negative If Only thoughts than positive At Least thoughts to our survival instinct. Because our brains are wired for survival, they are more likely to pay attention to a potential threat to our survival than something comforting. Pink suggests we pay attention to If Only counterfactuals even though they are uncomfortable because doing so could help us make better decisions in the future.

“The main effect, several studies show, is on our ‘decision hygiene.’ Leaning into regret improves our decision-making process—because the stab of negativity slows us down. We collect more information. We consider a wider range of options.”

Pink points out the correlation between negative experiences and the thought process necessary to learn from our mistakes and improve our decision-making. In other words, processing negative emotions like regret forces us to slow down and think of alternative solutions.

“In fact, other research has found that people who thought counterfactually about pivotal moments in their life experienced greater meaning than people who thought explicitly about the meaning of those events. The indirect paths of If Only and At Least offered a faster route to meaning than the direct path of pondering meaning itself. Likewise, when people consider counterfactual alternatives to life events, they experience higher levels of religious feeling and a deeper sense of purpose than when they simply recount the facts of those events. This way of thinking can even increase feelings of patriotism and commitment to one’s organization.”

Counterfactual thinking enables us to consider alternatives to past events. By thinking counterfactually, we may realize that regretful decisions have already made our lives better, either because they have led to other, positive events in our lives or because they have prevented problems. When we consider counterfactual possibilities, the decisions we made become more meaningful.

“Thinking is for doing. We act in order to survive. We think in order to act.”

Pink points out that the purpose of thinking is to help us survive. In this sense, acknowledging and analyzing regrets not only ensures that we avoid similar decisions in the future but provides us with the perspective necessary to make optimal decisions.

“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.”

Pink emphasizes the need for balance in coping with regret. One should not abandon regrets by embracing the adage “No regrets” and should likewise refrain from ruminating on and overidentifying with regrets. Instead, one should regard them objectively as a means of informing and optimizing future behavior.

“Kintsugi (which translates to ‘golden joinery’) considers the breaks and the subsequent repairs part of the vessel’s history, fundamental elements of its being. The bowls aren’t beautiful despite the imperfections. They’re beautiful because of the imperfections. The cracks make them better. What’s true for ceramics can also be true for people.”

Pink uses the Japanese art of kintsugi as a metaphor for the beauty of our imperfections and resilience in moving on from regret. That a kintsugi vessel’s beauty is found in its repaired cracks highlights the natural universality of regret and suggests that regret is an avenue for changing, perhaps for the better.

“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.”

Pink suggests that regret informs how we think, feel, and live—revealing human needs and values in the process. He invites us to consider the deep structure of regret so we can use them to better our self-knowledge and relationships.

“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.”

Pink links the fundamental attribution error, the tendency to attribute one’s behavior to disposition rather than a larger context, to foundation regrets. Foundation regrets may be rooted in factors outside of our control, such as a lack of guidance.

“There is something heartening about grown women and men waking up at night despairing over incidents decades earlier in their lives in which they hurt others, acted unfairly, or compromised the values of their community. It suggests that stamped somewhere in our DNA and buried deep in our souls is the desire to be good.”

Pink offers comforting thoughts regarding moral regrets. Although moral regrets are perhaps the most painful of the four core regrets (foundation, boldness, moral, and connection regrets), we can find comfort in the pain, knowing that regret over our failure to do the right thing shows we have a desire to be kind.

“Our concerns about the awkwardness of reconnecting with someone from whom we’ve drifted conform to this pattern. We too often presume that our own preferences are unique.”

Pink describes pluralistic ignorance, the assumption that our beliefs and preferences differ vastly from others’ beliefs and preferences. Because of this assumption, people hesitate to reach out to others—when in reality, many would appreciate someone reaching out to them.

“Happiness is love.”

George Vaillant, a Harvard psychiatrist who led the Grant Study for more than 30 years, concluded that humans need connection and love to live fulfilling lives. This conclusion explains why connection regrets are the most common type of regret.

“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.”

What people regret most often reflects what they value most. By thinking about our regrets from a healthy distance, we can discover what we value most and, by extension, determine what we need to do to make our lives better.

“The result is that opportunity and obligation sit at the center of regret, but opportunity has the more prominent seat.”

Regrets are often caused by failures to meet obligations or seize opportunities. Pink points out that regrets of inaction are more common than regrets of action because people think counterfactually about missed opportunities. Opportunity-related regrets are more common because there is often no reversing decisions.

“The other way to address the present is not to repair our previous actions but to recast the way we think about them.”

Because some decisions cannot be undone, Pink suggests that we view them differently, perhaps by At Leasting them (considering how a specific situation could have been worse). We might also consider what lessons or positives came out of the situation, even if indirectly.

“If we look backward with the specific intent of moving forward, we can convert our regrets into fuel for progress.”

Pink highlights the purpose of his book and one its main themes: The Power of Regret to prompt progress. He suggests that when we look backward and think about regrets, we should do so with intention. Rather than ruminating on regrets and allowing them to preclude us from being happy, we should have the “specific intent” of using them for positive change.

“The explanation—and 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.”

Through language (written or spoken aloud), we not only release our regrets but create distance from them, which enables us to think objectively about them and use them to cultivate positive change. If one chooses to release their regrets aloud, they can do so by sharing them with another person or recording thoughts through technology.