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The Power of Regret:

How Looking

Backward Moves

Us Forward

by Daniel Pink

After finishing this book in January of 2022, I wrote,


"Daniel Pink provides a compelling case for how to learn from our past 'regrets.' The issue he was not able to address, however, was the possibility of separating assessment from self-blame. Looking back over my life, I can find many things if I knew then what I know today, then I would have done it differently then. But I didn't know that then. So I have no self-blame, which for many means the same as regret."


My clippings below collapse a 255-page book into 6 pages, measured by using 12-point type in Microsoft Word.

See all my book recommendations.  

Here are the selections I made:


The seven-year-olds “performed very similarly to adults on the measures of the understanding of regret,” Guttentag and Ferrell write. Seventy-six percent of them understood that David would likely feel worse. But the five-year-olds showed little understanding of the concept. About three-fourths of them said the boys would feel the same.[4] It takes a few years for young brains to acquire the strength and muscularity to perform the mental trapeze act—swinging between past and present and between reality and imagination—that regret demands.


Only 1 percent of our respondents said that they never engage in such behavior—and fewer than 17 percent do it rarely. Meanwhile, about 43 percent report doing it frequently or all the time. In all, a whopping 82 percent say that this activity is at least occasionally part of their lives, making Americans far more likely to experience regret than they are to floss their teeth.


But the most common negative emotion—and the second most common emotion of any kind—was regret. The only emotion mentioned more often than regret was love.


A 2016 study that tracked the choices and behavior of more than a hundred Swedes found that participants ended up regretting about 30 percent of the decisions they’d made during the previous week.


But the truth is different. You’re much more likely to have a Silver Emma moment than a Bronze Borghini one. When researchers have tracked people’s thoughts by asking them to keep daily diaries or by pinging them randomly to ask what’s on their mind, they’ve discovered that If Onlys outnumber At Leasts in people’s lives—often by a wide margin.[7] One study found that 80 percent of the counterfactuals people generate are If Onlys.


Regret is the quintessential upward counterfactual—the ultimate If Only.


Perhaps you’re familiar with the First Law of Holes: “When you find yourself in a hole, stop digging.” And perhaps you’ve ignored this law.


The psychological concept is known as “escalation of commitment to a failing course of action.” It’s one of the many cognitive biases that can pollute our decisions.


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.


Foundation regrets arise from our failures of foresight and conscientiousness. Like all deep structure regrets, they start with a choice. At some early moment, we face a series of decisions. One set represents the path of the ant. These choices require short-term sacrifice, but in the service of a long-term payoff. The other choices represent the path of the grasshopper. This route demands little exertion or assiduousness in the short run, but risks exacting a cost in the long run.


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


At the heart of all boldness regrets is the thwarted possibility of growth.


One thirty-three-year-old South African woman spoke for many when she wrote: I regret not having the courage to be more bold earlier in my career and caring too much what other people thought of me.


A fifty-six-year-old man in Pennsylvania regrets “staying with my current company when I knew over fourteen years ago it would never satisfy,” just as a fifty-three-year-old man from Great Britain regrets “not leaving my safe job to follow my instinct and stay true to my core values sooner.” A fifty-four-year-old woman in Oregon regrets “not being bolder in my late thirties and taking a job in a new geographical area.” Then she collapses her regret to a single word: “Settling.”


Said a forty-eight-year-old Ohio man: I regret not being more adventurous . . . taking time to travel, explore, and experience more of what the world has to offer. I let the fear of disappointment rule me and allowed others’ expectations to be more important than my own. I was always the “good soldier” and worked hard to please those around me. I have a good life—I just wish I had more experiences to share with others. Someday . .


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.”


Take this fifty-three-year-old Californian: I regret not coming out as a gay man sooner. It definitely impacted how I showed up and my performance and connectedness with my colleagues.


The lesson is plain: Speak up. Ask him out. Take that trip. Start that business. Step off the train.


Moral regrets make up the smallest of the four categories in the deep structure of regret, representing only about 10 percent of the total regrets.


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: Children are more vulnerable than the offspring of other animals, so humans devote considerable time and effort to protecting them. As a result, evolution has instilled in us the ethic of care. Those who nurture and defend the vulnerable are kind; those who hurt them are cruel. Fairness/cheating: Our success as a species has always hinged on cooperation, including exchanges that evolutionary scientists call “reciprocal altruism.” That means we value those whom we can trust and disdain those who breach our trust. Loyalty/disloyalty: Our survival depends not only on our individual actions, but also on the cohesiveness of our group. That’s why being true to your team, sect, or nation is respected—and forsaking your tribe is usually reviled. Authority/subversion: Among primates, hierarchies nourish members and protect them from aggressors. 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.[5] Purity/desecration: Our ancestors had to contend with all manner of pathogens—from Mycobacterium tuberculosis to Mycobacterium leprae—so their descendants developed the capacity to avoid them along with what’s known as a “behavioral immune system” to guard against a broader set of impurities such as violations of chastity. 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.” [6] Moral foundations theory doesn’t say that care is more important than purity or that authority is more important than fairness or that you should follow one set of foundations instead of another. It simply catalogs how humans assess the morality of behavior. The theory is descriptive, not prescriptive. But its descriptive power is considerable. Not only did it reshape my understanding of both human reasoning and modern politics; it also offered an elegant way to interpret our moral regrets.


THE FIVE REGRETTED SINS Deceit. Infidelity. Theft. Betrayal. Sacrilege.


And the most common harm was bullying. Even decades later, hundreds of respondents deeply regretted mistreating their peers.


Regrets in this subcategory weren’t limited to childhood malice. People described insulting work colleagues, “ghosting” romantic interests, and threatening neighbors. Most hurts were delivered with words, though a few were with fists. And for all the American associations of behavior like bullying, these regrets were international.


What’s more, the regrets people expressed were less about renouncing the group than falling short of one’s obligations to it.


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.”


He regrets not having “the experience of hardship and sacrifice,” of depending on others for survival and of their relying on him. “If you’re serving someone, it means you’re not serving yourself,”


4. Subversion The fewest moral regrets involved the Authority/Subversion foundation. A handful of people regretted “dishonoring my parents” and “being disrespectful to my teachers”—like


Desecration Regrets about violating sanctity were more numerous than regrets about subverting authority. These regrets were also emotionally intense—especially when they centered on one of the most fiercely contested issues of the last sixty years: abortion.


A fifty-year-old woman in Arkansas said: I had an abortion at age twenty. That is the biggest regret of my life. My second-biggest regret is that I had another one at age twenty-five.


These regrets were partly about harm, but they were bigger than that: a belief that the actions amounted to a degradation of the very sanctity of life.


A fifty-eight-year-old woman in Puerto Rico regretted: Having an abortion. Having to say I’m sorry when I meet him/her in Heaven.


We don’t always agree on the boundaries between those domains. But when we forsake what we believe is sacred for what we believe is profane, regret is the consequence.


Moral regrets are a peculiar category. They are the smallest in number, yet the greatest in variety. They are the most individually painful.


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.


Connection regrets are the largest category in the deep structure of human regret.


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


Self-disclosure is intrinsically rewarding and extrinsically valuable. It can lighten our burden, make abstract negative emotions more concrete, and build affiliation. So, to begin to harness your regrets to improve in the future, try any of the following: 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.


Self-compassion emerged in part from Neff’s recognition that when we stumble or fail, we treat ourselves more harshly than we would ever treat friends, family, or even strangers in the same predicament. That’s counterproductive, she has shown. Rather than belittling or berating ourselves during moments of frustration and failure, we’re better off extending ourselves the same warmth and understanding we’d offer another person. Self-compassion begins by replacing searing judgment with basic kindness. It doesn’t ignore our screwups or neglect our weaknesses. It simply recognizes that “being imperfect, making mistakes, and encountering life difficulties is part of the shared human experience.”[15] By normalizing negative experiences, we neutralize them.


Some people find illeism annoying (although it doesn’t bother Daniel Pink). But its existence as a style of speech and narration exemplifies the final step in the regret-reckoning process. Talking about ourselves in the third person is one variety of what social psychologists call “self-distancing.” When we’re beset by negative emotions, including regret, one response is to immerse ourselves in them, to face the negativity by getting up close and personal. But immersion can catch us in an undertow of rumination. A better, more effective, and longer-lasting approach is to move in the opposite direction—not to plunge in, but to zoom out and gaze upon our situation as a detached observer, much as a movie director pulls back the camera. After self-disclosure relieves the burden of carrying a regret, and self-compassion reframes the regret as a human imperfection rather than an incapacitating flaw, self-distancing helps you analyze and strategize—to examine the regret dispassionately without shame or rancor and to extract from it a lesson that can guide your future behavior.


First, we can distance through space. The classic move is known, unsurprisingly, as the “fly-on-the-wall technique.”


The second way to self-distance is through time. We can enlist the same capacity for time travel that gives birth to regret to analyze and strategize about learning from these regrets.


The third method of self-distancing, as Julius Caesar and Elmo teach us, is through language. Kross, Ayduk, and others have carried out some fascinating research concluding that “subtle shifts in the language people use to refer to themselves during introspection can influence their capacity to regulate how they think, feel, and behave under stress.”


Start a regret circle. Think of regret circles as close cousins of book clubs. Gather five or six friends over coffee, tea, or drinks. Ask two of them to come prepared with a significant regret. Let them tell the story of their regrets. Have the others respond to each regret first by categorizing it. (Is it action or inaction? Into which, if any, of the four deep structure categories does it fall?) Then, for each regret, the group works through the Disclosure-Compassion-Distance process. When the gathering ends, the two people commit to adopting a specific behavior (for example, speaking up to an unpleasant boss or asking out a crush). At the next meeting, the others hold the regretters accountable for that promise—and two new people share their regrets.


Create a failure résumé. Most of us have a résumé—a written compendium of jobs, experiences, and credentials that demonstrate to prospective employers and clients how qualified, adept, and generally awesome we are. Tina Seelig, a professor of practice at Stanford University, says we also need a “failure résumé,” a detailed and thorough inventory of our flops. A failure résumé offers another method for addressing our regrets. The very act of creating one is a form of disclosure. And by eyeing your failure résumé not as its protagonist, but as an observer, you can learn from it without feeling diminished by your mistakes. A few years ago, I compiled a failure résumé, then tried to glean lessons from the many screwups I’d committed. (Disclosing these embarrassments to myself will be sufficient, thank you very much.) I realized I’d repeatedly made variations of the same two mistakes, and that knowledge has helped me avoid those mistakes again.


3. Study self-compassion.


Pair New Year’s resolutions with Old Year’s regrets.


Mentally subtract positive events. To take the hurt out of a regret, try a mental trick made famous in the 1946 movie It’s a Wonderful Life. On Christmas Eve, George Bailey stands on the brink of suicide when he’s visited by Clarence, an angel who shows George what life in Bedford Falls would be like had he never been born. Clarence’s technique is called “mentally subtracting positive events.”


Participate in the World Regret Survey. If you haven’t done so already, submit your regret to the World Regret Survey ( Putting your regret in writing can defang it—and can offer the distance to evaluate it and plan from it. You can also read other people’s regrets, which provides perspective on our shared humanity and can help strengthen your regret-reckoning muscles. As you read regrets from across the globe, ask yourself: What kind of regret is this? What advice would you give the writer for using her regret as a positive force?


Adopt a journey mindset.

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