The Power of Regret: How Looking Backward Moves Us Forward

Pink describes Noam Chomsky’s 1957 book Syntactic Structures, which argues that language is built upon “rules lodged in the human brain” (75). In his book, Chomsky argues language is an innate capacity and that different languages only differ on the surface. Regret, too, has both a “surface structure and a deep structure” (77). The categories of regret that are easy to describe (i.e., family, education, and work) are far less significant than the “hidden architecture of human motivation and aspiration that lies beneath” them (77).

By parsing recurring words and phrases from the thousands of responses received for the American Regret Project, Pink found “clues to a deep structure” and established four “categories of human regret” (78). Foundation regrets involve the failure to be responsible; boldness regrets involve chances we did not take; moral regrets involve “morally dubious decisions” we made (79); and connection regrets involve allowing relationships to drift apart.

Pink describes the biggest regret of Jason Drent, a man who achieved success only to squander his money and destroy any promise of future abundance despite his hard work. He aligns Drent’s story with Aesop’s fable “The Ant and the Grasshopper,” in which the grasshopper enjoys himself in the moment while the ants work hard to gather food for the future. Once winter arrives, the grasshopper dies of hunger, while the ants eat well and survive. Drent’s predicament falls into the category of foundational regrets, which “arise from our failures of foresight and conscientiousness” (85). Foundational regrets include not only financial failures but the failure to take care of one’s health. By “partying all summer” instead of preparing for the winter, the grasshopper “succumbed to what economists call “temporal discounting,” which means he overvalued the present and undervalued the future. Likewise, Drent’s feeling of invincibility while achieving early success obstructed foresight of his future needs (86).

Pink notes that to identify a foundational regret, one should pay attention to phrases such as “too much,” whether they are linked to activities such as consuming alcohol, playing video games, watching television, spending money, or “any other activity whose immediate lure exceeds its lasting value” (88). Likewise, one should pay attention to the phrase “too little” when describing studying, practicing a hobby, saving money, or “any other undertaking that requires steady commitment” (88). Pink states that people tend to experience foundational regrets gradually, and then suddenly. Some missteps are not immediately devastating, but the repetition of adverse behaviors over time yields a sudden realization that the adverse behaviors have gone on too long—and it may be too late to reverse the damage.

Pink notes a trend in some of the responses to the American Regret Project: acknowledgment of the compounding effect of one’s actions or inactions. Small actions taken on a regular basis such as eating well, exercising, studying, and working “produce explosive benefits or harms over time” (90). Although the immediate benefits or harms may seem miniscule, they accelerate over time. Because of the compounding effect of these types of actions or inactions, foundational regrets are “not just difficult to avoid,” but “difficult to undo” (90).

Pink states that foundational regrets are “trickier” than others because of the lack of clarity as to whether or not the person experiencing the regret is wholly at fault. For example, perhaps a healthy lifestyle or financial responsibility were not taught or modeled to the person, and because of this, the person lacked the perspective needed to make optimal decisions. Pink states that one of the most prevalent cognitive biases is the “fundamental attribution error,” which aligns someone’s behavior with their disposition rather than their “situation and context” (94). He aligns this cognitive bias with what he calls “foundation attribution error,” which is our tendency to judge ourselves and others for choices when some of the circumstances that led to these choices cannot be controlled. He concludes 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” (94). Because of this, Jason Drent acts as a mentor to young people; he encourages them to save some of their earnings for the future. Drent wishes older people would have guided him to be more prudent with his money when he was younger. Overall, “deep structure regrets reveal a need and yield a lesson,” and foundational regrets reveal a need for stability (95).

In November 1981, a 22-year-old American man named Bruce was on a train traveling through France when he met a woman. They made easy conversation and eventually held hands. When the train arrived at the woman’s stop, Bruce offered to come with her, but the woman exclaimed, “My father would kill me!” (99). They kissed, and Bruce gave the woman a piece of paper with his name and his parents’ address. Forty years later when he completed the World Regret Survey, Bruce stated he regrets not stepping off the train. Bruce’s regret is considered a boldness regret. Boldness regrets are regrets about not taking chances. Although the women eventually wrote Bruce a short note, she did not leave her name or address, thereby halting communication.

Pink states that in the American Regret Project, “inaction regrets outnumbered action regrets by nearly two to one” (104). He attributes this to the fact that when people act, they know the result of their actions, whereas when they fail to act, there is the allure of the unknown. There is no certainty as to what would have happened, only speculation. Pink states, “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” (105). Boldness regrets include not pursuing a potential romantic partner, a business venture, or any other opportunity. They also include not being true to oneself (in regard to gender, sexuality, et cetera), thereby denying oneself the chance to live fully. Pink concludes that “[w]ith 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” (110).

Pink writes about a World Regret Survey participant’s regret about having an affair with one of her husband’s friends. Moral regrets make up only 10 percent of total regrets, the least of any category, but are often the most painful—as they involve failing to do the right thing. Pink then describes Jonathan Haidt’s book The Righteous Mind: Why Good People Are Divided by Politics and Religion. In this book, Haidt claims that determining whether or not something is moral is based not on a reasoned evaluation but on an “instantaneous, visceral, emotional response about right and wrong” (115). We then use reason to justify the intuition. Pink also describes Haidt’s “moral foundations theory,” which suggests that beliefs about morality stand on five pillars: care/harm, fairness/cheating, loyalty/disloyalty, authority/subversion, and purity/desecration (117-18). As such, Pink frames moral regrets as stemming from harm, cheating, disloyalty, subversion, and desecration.

In both the American Regret Project and the World Regret Survey, people reported more harm-related regrets than any other, with the most common being bullying. Pink states that unlike boldness regrets, moral regrets are more likely to involve actions rather than inactions—people regret things they did that hurt others. Steve Robinson, for example, regrets bullying his classmates when he was in eighth grade, especially when he punched one of his classmates and broke their two front teeth. Because of his regret, Steve now tries to be a better person and make people feel safe.

While regrets about harming others through actions such as bullying were the most pervasive, regrets about cheating, especially in marriages, “finished a close second” in the World Regret Survey (122). People seem to regret the “trust they shattered” through their infidelity. Outside of relationships, people also regret falling short of one’s obligations to a certain group, such as their country; some people regret not having served their country by joining the military.

The fewest moral regrets involved subverting authority. Only a handful of people regretted dishonoring one’s family and teachers. Pink attributes the scarcity of this type of regret to the fact that the survey only sampled Americans, and these regrets are more prominent in other cultures. He states that regrets about desecration were far more common than those about subverting authority. Although not as common as regrets about bullying and infidelity, they were prevalent. Pink states that these regrets were “bigger than” harm in that they were based on “a belief that the actions amounted to a degradation of the very sanctity of life” (127). Overall, moral regrets are the smallest in number, but are the greatest in variety, the “most individually painful” (129). However, this type of regret suggests that humans desire to be good.

Pink describes a friendship between two women that drifted. One of the survey respondents, Cheryl Johnson, stated that after not talking to her former friend for 25 years, she wants her to know that their friendship is still significant despite the lapse in time (132). She wants to reach out to her friend but is afraid to.

According to Pink, “Connection regrets are the largest category in the deep structure of human regret” (132). Connection regrets include platonic and romantic relationships. Although these regrets may be unsalvageable due to death, some relationships are able to be mended. However, people are often too timid to reach out to estranged family and friends, among others. Doing so not only requires effort but is laden with uncertainty and the risk of rejection.

Pink describes another woman, Amy Knobler, who had a childhood friend whom she had put off calling. Eventually, Amy did call her, only to find out that she had died from cancer. Amy regrets not calling sooner and feared that her friend had died wondering why she never called. Pink makes a distinction between closed-door regrets and open-door regrets. While one can rectify an open-door regret by reaching out to a person, a closed-door regret, such as one resulting from a person’s death, cannot be fixed. Pink states that both types of regret linger for different reasons: While open-door regrets bother people because they require effort to fix, closed-door regrets bother people because there is nothing than can be done.

A 2012 study by Kai Epstude, Mike Morrison, and Neal Roese concluded that regrets about relationships are more intense than other types of regrets because “they threaten our sense of belonging” (136). Pink divides connection regrets by two causes: rifts and drifts. While rifts are caused by a specific incident, such as fights, threats, and resentment, drifts occur gradually, without a “discernible beginning, middle, or end” (137). Rifts are more dramatic but less common than drifts. When drifts occur, people often feel uncomfortable reaching out after time has elapsed, uncertain where they stand with estranged family and friends, among others.

In a 2014 study, social psychologists Nicholas Epley and Juliana Schroeder recruited commuters on trains and buses in Chicago and asked them to strike up conversations with random passengers. Although the participants’ assumptions were that doing so would create discomfort, they were wrong. They found that both the participants who initiated conversations and the strangers they conversed with enjoyed their commute more. Epley and Schroeder concluded that “People misunderstand the consequences of social connection” (140).

Likewise, in a 2020 study, Erica Boothby of the University of Pennsylvania and Vanessa Bohns of Cornell University examined people’s reluctance to compliment others. People often worry that giving compliments will make a recipient feel uncomfortable, but the study found that the opposite was true.

The commute study and the compliment study share what social psychologists call “pluralistic ignorance”—a phenomenon in which “we mistakenly assume that our beliefs differ vastly from everyone else’s, especially when these private thoughts seem at odds with broader public behavior” (140). For example, when students don’t ask questions, it is often because they erroneously believe others will judge them as unintelligent if they do ask questions. Pink connects this phenomenon to the belief that reconnecting with someone from the past is inherently uncomfortable. We often believe we are the only party who wants to reach out when the other party may want to reach out too.

Pink describes the “longest-running examination of the lifetime well-being of a single group of people”—the Study of Adult Development, or the Grant Study. Beginning in 1938, researchers at Harvard followed 268 undergraduate men for the 80 years, taking into account their IQs, lifetime earnings, and other attributes. The purpose was to determine why some people flourished in work and life, while others did not. Although the study only represents white American men, its conclusions were significant. In 2017, the Harvard Gazette concluded that “Close relationships, more than money or fame, are what keep people happy throughout their lives” (141). The same year, Robert Waldinger, a psychiatrist and the current director of the study (at the time of the book’s publication) stated, “Taking care of your body is important, but tending to your relationships is a form of self-care too” (142). Such findings aligned with many of the regrets voiced in the World Regret Survey, including not being affectionate with a stepchild and not being supportive of a child who came out as transgender. George Vaillant, another Harvard psychiatrist who had led the Grant Study for more than 30 years, concluded that “[h]appiness is love” (144). Pink states that the human need linked with connection regrets is love, and the lesson learned from closed-door regrets is to “do better next time,” while the lesson of open-door regrets is to “do something now” (145).

Pink opens this chapter with a metaphor about regret. He compares regret to photographic negatives, the middle step of the production process when developing a photograph. When printed, the light and dark of the photograph are reversed, and the original color tones restored. The four core regrets (foundation, boldness, moral, and connection regrets) similarly reflect the negative image of a good life. Pink states, “If we know what people regret the most, we can reverse that image to reveal what they value the most” (149). In evaluating the four core regrets, Pink concludes that people seek a “measure of stability,” hope to use some of their time to “explore and grow,” aspire to “do the right thing,” and “yearn to connect with others” (150).

In 1987, Tory Higgins, a Columbia University social psychologist, proposed that people have an “‘actual self,’ an ‘ideal self,’ and an ‘ought self’” (150). Our “actual self” is composed of attributes we possess; our “ideal self” is the self of our dreams and aspirations, the self we believe we could be; the “ought self” is who we believe we should be, based on our commitments and responsibilities. Higgins argued that the discrepancies between these three selves guide our behavior and goals. For example, if one’s ideal self is healthy and physically fit, but their actual self is tired and overweight, the person may start exercising to mend the discrepancy between the two selves. Likewise, if a person believes they should have a better relationship with their grandmother, but their actual self has not reached out to her in months, they may be motivated to finally visit. Pink states that “when we don’t make these efforts, when a discrepancy persists between who we are and who we could or should be, unpleasant feelings flood the gap” (151).

A 2018 study by Shai Davidai of the New School for Social Research found that “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” (151). Pink believes the likely reason for this disparity is that failure to live up to our ought selves motivates us to act, while failure to live up to our ideal selves leads us to feeling dejected. There is a greater sense of urgency to rectify ought-related regrets. Because of this, could-related regrets last longer because they are less likely to be fixed. Pink defines ought-related regrets as obligation regrets and could-related regrets as opportunity regrets. He concludes that “opportunity and obligation sit at the center of regret, but opportunity has the more prominent seat” (151).