The Power of Regret

The Power of Regret Plot Summary

Introduction

The morning air was crisp as Sarah stood at her kitchen window, coffee in hand, gazing at the old oak tree in her backyard. Twenty years ago, she had planted that tree with her father, just months before he passed away. As she traced its growth rings in her mind, she felt a familiar pang—not just of loss, but of regret. "I wish I had asked him more questions," she whispered. "About his childhood, his dreams, the war years." The opportunity was gone forever, leaving behind that peculiar ache that comes from knowing something could have been different. Regret is perhaps our most misunderstood emotion. We're told to have "no regrets," to look forward rather than backward, to embrace positivity and shun negative feelings. Yet as this profound exploration reveals, regret isn't a burden to be avoided but a resource to be harnessed. By examining thousands of lives across cultures and contexts, we discover that regret—when properly understood—serves as a unique catalyst for growth, better decisions, and deeper meaning. Far from being a toxic emotion that drags us down, regret can actually lift us up by clarifying what matters most, illuminating paths not taken, and redirecting our future choices. Through compelling research and moving human stories, we learn to transform the pain of "what might have been" into the wisdom of "what still could be."

Chapter 1: The Myth of 'No Regrets': Why We Need This Emotion

Jason was twenty-two when he walked into a tattoo parlor in Colorado Springs and had the words "NO REGRETS" inked across his left bicep. The irony wasn't lost on him when, fourteen years later, he found himself paying ten times the original cost to have those very words removed. "I got the tattoo when I thought being tough meant never looking back," he explained. "Now I realize that was just fear disguised as strength." Jason's story reflects our culture's complicated relationship with regret. From Edith Piaf's defiant anthem "Non, Je Ne Regrette Rien" to countless social media posts hashtagged #NoRegrets, we're surrounded by messages that frame regret as weakness. Celebrities routinely proclaim they "don't believe in regrets." Self-help gurus advise us to "leave regrets in the past." Even religious and spiritual leaders often counsel against dwelling on what cannot be changed. This anti-regret philosophy seems intuitively correct. Why invite pain when we can avoid it? Why summon rain clouds when we can bathe in sunshine? Why rue yesterday when we can dream about tomorrow? The logic appears sound—except for one significant flaw: it's profoundly wrong. What science has discovered is that regret isn't dangerous or abnormal. It's healthy and universal—an integral part of being human. The ability to feel regret is so fundamental to our development that its absence can signal serious brain damage. Studies of patients with lesions on their orbitofrontal cortex reveal they cannot experience regret at all, which impairs their decision-making abilities. Far from being an emotional defect, regret is a sophisticated cognitive achievement that requires mental time travel and counterfactual thinking—imagining how things might have been different. When we understand regret properly, we see it not as an enemy of happiness but as a teacher of wisdom. It clarifies our values, deepens our sense of meaning, and offers instructions for living better. The pain it causes serves a purpose—like a warning light on a dashboard, it alerts us to what matters most. The challenge isn't to eliminate regret but to transform it from a source of paralysis into a catalyst for growth.

Chapter 2: The Four Core Regrets That Define Our Lives

Maria was fifty-eight when she completed the World Regret Survey, sharing what she called her "life's greatest mistake." After thirty years in accounting, she wrote: "I regret not pursuing my passion for marine biology. I was good at math and everyone said accounting was practical, so I listened to them instead of myself. I've had a comfortable life, but not the one that would have made me feel alive." Maria's regret might seem unique to her circumstances, but it represents a pattern that emerges when thousands of regrets are analyzed. While our individual stories differ, the underlying structure of human regret is remarkably consistent. After collecting and studying more than 16,000 regrets from people in 105 countries, a surprising discovery emerged: beneath the surface details of our diverse lives, four core regrets appear again and again. Foundation regrets arise when we fail to be responsible, conscientious, or prudent early in life. These are the "if only I'd done the work" regrets—not saving money, neglecting education, or ignoring health. Like the grasshopper in Aesop's fable who fiddles away the summer while the ant prepares for winter, we prioritize immediate pleasure over long-term security, only to watch small choices compound into major consequences. Boldness regrets stem from opportunities not taken—"if only I'd taken that risk." The romance never pursued, the business never started, the countries never visited. Research consistently shows that over time, we regret inaction more than action. The paths not taken haunt us more persistently than the mistakes we made while trying. As one seventy-year-old man wrote: "I regret all the bold moves I didn't make, all the chances I didn't take, all the times I played it safe." Moral regrets occur when we violate our own ethical code—"if only I'd done the right thing." Whether through acts of commission (like cheating on a partner) or omission (failing to stand up for someone), these regrets reveal our deep desire to be good people. They represent the gap between the person we want to be and the person our actions sometimes reveal us to be. Connection regrets involve relationships that have come undone or never fully formed—"if only I'd reached out." The friendship that drifted away, the sibling not spoken to for years, the parent never truly known. These regrets are especially poignant because they often involve what psychologists call "psychological asymmetry"—we want to reconnect but fear the other person doesn't, when in reality they likely feel the same way. These four core regrets aren't just categories of pain—they're windows into our deepest human needs: stability, growth, goodness, and love. By revealing what we find most regrettable, they illuminate what we find most valuable. The negative emotion of regret offers a photographic negative of the positive life we truly desire.

Chapter 3: Foundation Regrets: The Price of Irresponsibility

Jason Drent was only eighteen when he landed his first full-time job at Best Buy. Within a few years, his work ethic had propelled him to become the youngest sales manager in company history. His career continued to soar—district manager, regional manager, executive positions that took him across the country and earned him six-figure salaries. By all appearances, Jason was a success story—a young man who had overcome a difficult childhood to build an impressive career in corporate America. But at age forty-three, Jason submitted this to the World Regret Survey: "I regret not saving money diligently ever since I started working. It's nearly crushing every day to think about how hard I've worked for the last twenty-five years, but financially I have nothing to show for it." Despite his sterling résumé, Jason had barely a dime in the bank—a positive record of achievement but a negative net worth. From his first paycheck, Jason had vowed to himself, "I'm going to buy whatever I want as soon as I can." He wasn't particularly extravagant—just a decent car, some clothing, the pride of picking up restaurant tabs with friends. These small daily choices felt good in the moment but haunted him years later. "I should have more resources at this point," he reflected. "It was twenty-five years of fiddling." Foundation regrets like Jason's follow a predictable pattern. They begin with what economists call "temporal discounting"—overvaluing immediate rewards and undervaluing future benefits. We choose the path of the grasshopper rather than the ant, spending too much and saving too little, applying minimal effort in school, neglecting our health. The consequences of these choices don't materialize immediately. Instead, they accrue slowly, almost imperceptibly, until one day the accumulated weight becomes impossible to ignore. What makes foundation regrets particularly painful is that they often involve compounding effects. Just as compound interest can exponentially increase savings over time, poor foundation choices compound in the opposite direction. A small decision at age twenty—skipping classes, maxing out credit cards, avoiding exercise—might seem inconsequential. But by forty or fifty, that same choice has multiplied into life-altering consequences that can't easily be undone. In his current job overseeing workplace policies for a large retailer, Jason now tries to help young employees avoid his mistakes. "I'm very transparent about being forty-three and not having any money," he said. "I only wish more forty-three-year-olds had been honest with me when I was younger. I'm telling the cautionary tale of the grasshopper." The lesson of foundation regrets is simple but powerful: Think ahead. Do the work. Start now. The best time to plant a tree was twenty years ago. The second-best time is today.

Chapter 4: Boldness Regrets: The Pain of Unexplored Paths

In November 1981, a twenty-two-year-old American named Bruce was on a train speeding through France when a young woman boarded at a Paris station and took the seat beside him. Bruce's French was meager, but the woman's English was decent, and they began talking. Bruce had spent the past year in Europe, living with a family in Sweden and hitchhiking across the continent. Now he was heading to Stockholm to catch a flight back to the United States. The woman, a brunette perhaps a year or two younger than he, was from Belgium. She'd been working in Paris as an au pair and was traveling back to her small Belgian hometown. The conversation flowed easily. Soon they were laughing, playing hangman, and doing crossword puzzles together. Before long, they were holding hands. "It was truly as if we had known each other our whole lives," Bruce recalled. "And I have never felt that way again." Just before midnight, as the train approached a station in Belgium, the woman stood up and told him, "I have to go." Bruce impulsively said, "I'll come with you!" She replied, "Oh, God, my father would kill me!" They walked to the door. They kissed. Bruce scribbled his name and his parents' Texas address on a slip of paper and handed it to her. The train doors opened, she stepped off, and the doors closed. Bruce never even learned her name. Forty years later, he submitted his story to the World Regret Survey, concluding: "I never saw her again, and I've always wished I stepped off that train." Boldness regrets like Bruce's arise from opportunities not seized—chances to take risks that might have led to growth, fulfillment, or transformation. Research consistently shows that over time, people regret inactions more than actions. As psychologists Thomas Gilovich and Victoria Medvec discovered, "Regrettable failures to act have a longer half-life than regrettable actions." When we act and fail, we know what happened next. The story has an ending. But when we don't act—when we don't step off that metaphorical train—we can only speculate endlessly about how events might have unfolded. This pattern appears across cultures and contexts. People regret not asking someone out, not starting a business, not traveling when they had the chance, not speaking up in crucial moments. A 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." What makes boldness regrets so poignant is that they often involve the thwarted possibility of growth—the failure to become the person we might have been. As one survey respondent put it: "My deepest regret of my fifty-two years of life is having lived it fearfully. I have been afraid of failing and looking foolish, and as a result, I did not do so many things that I wish I had done." At heart, boldness regrets reveal our fundamental human need for exploration, novelty, and the expansion of our capabilities and experiences. They remind us that while stability matters, so does the courage to occasionally step into the unknown.

Chapter 5: Moral Regrets: When We Betray Our Principles

Steve Robinson moved to Muncie, Indiana, in eighth grade. He was a small kid, introverted and socially awkward. But he compensated for these perceived deficits by becoming a menace. He taunted and teased his classmates. He picked fights. At age sixteen, he punched a fellow student and broke his two front teeth. Now, at age forty-three, these gratuitous aggressions are Steve's deepest regrets. "Having been on both sides of it, and knowing what it felt like, and then still having done it to someone else, is what I find most regretful," he told an interviewer. In the moments preceding the bullying, "I knew I shouldn't be doing this." Yet he did it anyway. He enjoyed the attention. He relished the feeling of power. But he knew better. Moral regrets like Steve's arise when we face a choice between right and wrong—and choose wrong. We hurt others. We break our promises. We betray our principles. And while the decision might feel fine or even exhilarating in the moment, over time it gnaws at us. As one fifty-seven-year-old man from South Africa wrote: "I regret telling a woman I was dumping her because she was fat. Thirty years later I'm waking up at night in disbelief at the hurt I caused then." What makes moral regrets particularly powerful is that they directly challenge our self-image as good people. Most of us want to believe we're decent, honorable, and trustworthy. When our actions contradict that belief, we experience cognitive dissonance—a psychological discomfort that demands resolution. We can resolve this dissonance either by rationalizing our behavior ("She deserved it" or "Everyone does it") or by acknowledging our failure and using it as motivation to do better. Moral regrets typically fall into several categories. Harm regrets involve hurting others through actions like bullying, insults, or physical aggression. Cheating regrets involve breaking promises or violating trust, especially in relationships. Loyalty regrets stem from betraying groups we belong to, while purity regrets involve violating sacred values. Across these categories, the common thread is the gap between who we aspire to be and who our actions reveal us to be. For many people, moral regrets become catalysts for redemption. After graduating from high school, Steve earned degrees in psychology, nursing, and criminal justice. He's worked as a pediatric nurse and as a counselor to delinquent children. "I've done badly by people in the past and I want to do right by people in my current state," he explained. "There's a certain part of me that takes a lot of pride in trying to make people feel safe these days." This transformation points to the deeper purpose of moral regrets: they remind us of our capacity for both harm and healing. By revealing the consequences of our ethical failures, they strengthen our commitment to living according to our highest values. The lesson of moral regrets is both ancient and urgent: when in doubt, do the right thing.

Chapter 6: Connection Regrets: The Relationships We Let Slip Away

Cheryl Johnson and Jen became fast friends in college in the late 1980s. Among the forty women in their sorority house, these two stood out for their seriousness and ambition. Cheryl became president of the sorority; Jen was elected president of the entire student body. "We took our college careers a little more seriously than the typical student, and that made us oddballs," Jen recalled. "We connected in part because we felt on the fringes of things socially." Shortly after graduation in 1990, Jen married—Cheryl was a bridesmaid—and moved to Virginia. Jen invited Cheryl to visit her new home, suggesting she might like to meet a friend of Jen's husband. Cheryl politely declined. No drama. No hard feelings. Over the next few years, living in different parts of the country in a time before widespread email, they exchanged letters and cards. But within a couple of years, the correspondence dwindled, then stopped. Cheryl hasn't talked to Jen for twenty-five years. They haven't seen each other in person since Jen's wedding. "We didn't have a falling out of any kind. I just let it kind of drift away," Cheryl explained. "I regret not having that relationship in my life. I've missed having another person in my life who could share with me the kind of growth I've experienced over the years." Connection regrets like Cheryl's are the largest category in what researchers call the "deep structure" of human regret. They arise from relationships that have come undone or remain incomplete. The specific relationships vary—spouses, partners, parents, children, siblings, friends, colleagues—but the plotline is consistent: a relationship that was once intact, or that should have been intact, no longer is. These regrets typically take one of two forms: rifts or drifts. Rifts begin with a catalyzing incident—an insult, a disclosure, a betrayal—that leads to a clear break. Drifts follow a muddier narrative. They lack a discernible beginning, middle, or end. One day the connection exists; another day it's gone. As a Pennsylvania woman wrote: "Not taking time to be a better friend, sister, daughter. Letting time slip away and suddenly realizing that I'm forty-eight." What makes connection regrets particularly painful is that they often involve what psychologists call "psychological asymmetry." When relationships drift apart, we want to reach out but fear rejection. We worry it would be awkward or unwelcome. Yet research shows we consistently overestimate how uncomfortable reconnection will be and underestimate how positively others will respond to our overtures. As Nicholas Epley and Juliana Schroeder found in their studies, "People misunderstand the consequences of social connection." The Harvard Study of Adult Development, which has followed the same group of men for more than eighty years, offers profound insight into what makes a good life. Its conclusion is remarkably simple: "Close relationships, more than money or fame, are what keep people happy throughout their lives." Those ties protect people from life's discontents, help delay mental and physical decline, and predict long and happy lives better than social class, IQ, or even genes. This research aligns with what many people express in their connection regrets—a recognition, often too late, of relationships' centrality to wellbeing. As one sixty-two-year-old wrote: "Both my parents, although a year apart, did their hospice at my home. I deeply regret not spending more time on their last days holding hands and speaking about the lovely moments they gave me. We weren't a family that hugged, cried, or kissed, and I didn't know I needed to do that—for them or for me." The lesson of connection regrets is both simple and profound: If a relationship you care about has come undone, place the call. Make that visit. Say what you feel. Push past the awkwardness and reach out.

Chapter 7: Transforming Regret: A Three-Step Process for Growth

Amy Knobler grew up in Cherry Hill, New Jersey. In middle school, she met a girl named Deepa. They became close friends, spending afternoons at Deepa's house after school. Amy remembers those times as some of the happiest of her life. The girls stayed friendly through high school and beyond. Deepa came to Amy's wedding in 1998, and Amy's parents attended Deepa's wedding in 2000. In 2005, Deepa was diagnosed with an aggressive form of cancer. Her prognosis fluctuated—she went into remission, had a baby, but in summer 2008, the cancer returned. Amy wanted to call her old friend. Amy put off calling her old friend. Late one night in December 2008, Amy learned that Deepa's health had taken a serious downturn. The following day, when Amy finally called Deepa's home, she discovered her friend had died that morning. "I will never forget how much I realized in that moment the opportunity that had been lost to me," Amy said. "My thought always was, 'Did she die wondering why I never called?' I will always wonder, and I just swore I was never going to behave that way again." Amy's experience illustrates what psychologists call a "closed door" regret—one where the opportunity to make amends is permanently gone. But her story also reveals how we can transform even our most painful regrets into fuel for growth. Research shows that when handled correctly, regret can sharpen our decision-making, elevate our performance, and deepen our sense of meaning through a three-step process. The first step is self-disclosure—reliving and relieving the regret by sharing it with others or writing about it privately. Princeton psychologist Diana Tamir discovered that talking about ourselves activates the same reward centers in our brains as food, money, and sex. When we disclose our regrets specifically, we convert abstract emotions into concrete language, which helps us process them. As James Pennebaker's groundbreaking research has shown, writing about emotional difficulties for just fifteen minutes a day can improve physical health, strengthen immune function, and enhance psychological wellbeing. The second step is self-compassion—normalizing and neutralizing the regret by treating ourselves with the same kindness we'd offer a friend. When we stumble or fail, we often treat ourselves more harshly than we would treat others in the same predicament. University of Texas psychologist Kristin Neff has shown that replacing self-criticism with self-compassion doesn't foster complacency—it actually increases motivation and improves performance. "Far from being an excuse for self-indulgence," Neff writes, "self-compassion pushes us forward—and for the right reasons." The final step is self-distancing—analyzing and strategizing about the lessons we've learned by zooming out in time, space, or language. When we're beset by negative emotions, immersing ourselves in them can lead to rumination. A more effective approach is to view our situation as a detached observer. Ethan Kross of the University of Michigan has found that using the third person ("she" instead of "I") when reflecting on challenges increases intellectual humility and improves problem-solving. Similarly, imagining how we'll feel about a regret in ten years helps us extract its lessons without being overwhelmed by its pain. Amy applied these principles when, years after Deepa's death, another childhood friend was diagnosed with cancer. "I kept revisiting my previous experience," Amy said. "I really needed to get myself on board for however difficult this would be." She called this friend frequently, visited her, and maintained their connection until the friend passed away in 2015. "It didn't make it easier. But I don't have regrets." This three-step process—disclosure, compassion, and distance—offers a systematic way to transform regret from a source of pain into a catalyst for growth. By looking backward with the specific intent of moving forward, we can convert our regrets into fuel for progress, propelling us toward smarter choices, higher performance, and greater meaning in the future.

Summary

Imagine standing at a crossroads in a dense forest. Behind you lies the path you've traveled, with all its wrong turns and missed opportunities. Ahead stretches the unknown future. The conventional wisdom says: "Don't look back. Regret nothing. Keep your eyes forward." But this exploration of our most misunderstood emotion reveals a profound truth: sometimes the best way to move forward is to look backward with clarity and purpose. The four core regrets—foundation, boldness, moral, and connection—serve as a photographic negative of the good life. By revealing what we find most regrettable, they illuminate what we find most valuable: stability, growth, goodness, and love. When we understand regret not as a burden to be avoided but as a resource to be harnessed, we gain access to its transformative power. Through self-disclosure, we relieve the weight of carrying regrets alone. Through self-compassion, we recognize our mistakes as part of our shared humanity rather than evidence of personal deficiency. Through self-distancing, we extract wisdom from our experiences that guides our future choices. In this way, regret becomes not just something we endure but something that propels us toward our best selves. As one seventy-year-old survey respondent wrote after reflecting on decades of both action and inaction: "Regret doesn't diminish me—it completes me. It shows me where I've been and points me toward where I still can go." The power of regret lies not in its ability to make us feel bad about the past, but in its capacity to make us brave about the future.

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Daniel H. Pink

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