The Power of Regret

When was the last time you lay awake thinking, “If only…”? Most of us have been told to live life with “no regrets,” to move fast and never look back. But what if that very avoidance of regret is what keeps us from living fully? In The Power of Regret, Daniel H. Pink dismantles the glossy self-help mantra of “no regrets” and argues that regret is not only normal but profoundly useful. It’s our most misunderstood emotion—an internal compass that, when handled well, can sharpen decisions, boost performance, deepen meaning, and connect us to what truly matters.

Why Regret Deserves a Second Look

Pink opens with a vivid contrast: the tough-minded declaration of Edith Piaf’s anthem “Non, je ne regrette rien” (“I regret nothing”) and the reality that even Piaf’s life was riddled with loss, addiction, and heartbreak. From tattooed “No Regrets” evangelists to self-help gurus, this cultural creed insists we suppress past pain and stay relentlessly positive. Pink calls this belief dangerous nonsense. Genuine happiness, he insists, isn’t about eliminating regret—it’s about harnessing it. Regret, properly examined, is a cognitive and emotional process that cuts to the core of human decision-making. It shows us not just what we did wrong, but who we want to be. Pretending we have no regrets is like pretending we have no spine—it robs us of our structure and growth.

Regret Makes Us Human—and Better

Pink draws on psychology, neuroscience, and his global research project to show that regret is a universal emotion. From the American Regret Project—a survey of over 4,400 Americans—and the World Regret Survey, which collected 16,000 responses from 105 countries, he uncovered a universal pattern: 82% of people look back on their lives wishing they’d done things differently. Across cultures, classes, and ages, regret outranked anger, jealousy, and disappointment; it was second only to love in everyday conversation. Its prevalence is no accident—it signals something essential about consciousness. Humans alone can time travel mentally, comparing what happened to what might have been, judging ourselves against alternate realities. Regret is our species’ way of learning from simulation. When we regret, we stretch the mind across time to imagine better futures.

Yet Pink doesn’t stop at sentiment. Decades of research—by psychologists such as Neal Roese, Thomas Gilovich, and Marcel Zeelenberg—prove that regret is a tool for self-correction. It refines our judgment (“I shouldn’t have done that”) and spurs positive change (“Next time, I’ll…”) when handled correctly. The absence of regret, Pink notes, isn’t a hallmark of enlightenment—it’s often a sign of brain damage, observed among patients with orbitofrontal cortex lesions. Regret, paradoxically, is evidence of a healthy, functioning conscience.

What Creates Regret—and What It Reveals

One of Pink’s biggest insights is that surface-level regrets (like lost jobs or failed relationships) hide a deeper architecture of motivation. Across thousands of survey responses, four fundamental patterns emerged: foundation regrets (failing to plan or prepare), boldness regrets (not taking a risk), moral regrets (violating one’s values), and connection regrets (letting relationships slip away). These “four core regrets” reveal the blueprint of the good life: stability, growth, goodness, and love. Knowing what people most regret illuminates what we most value. Our disappointments, he writes, operate like photographic negatives; by reversing them, we see the picture of what truly matters.

Foundation regrets worry about what we “didn’t build.” Boldness regrets ache for the lives we “didn’t live.” Moral regrets expose the times we “didn’t act right.” Connection regrets mourn the moments we “didn’t reach out.” Together they form a mirror of our aspirations and a map for better living. Regret, Pink shows, isn’t the enemy—it’s a teacher whispering, “Here’s what you care about most.”

From Emotional Pain to Practical Wisdom

How, then, do you turn regret from tormentor to tutor? Pink’s final sections offer a pragmatic guide. He introduces undoing, reframing, and self-compassion as tools for making peace with the past. Instead of suppressing or wallowing, he suggests a three-step process: disclose your regret (to lessen its emotional weight), practice self-compassion (treat yourself with kindness instead of contempt), and create self-distance (analyze your regret as an observer rather than a victim). Regret, when met with curiosity rather than shame, transforms self-punishment into self-knowledge.

Finally, Pink explores “anticipated regret”—how imagining your future remorse can help guide present choices. It’s the logic behind Jeff Bezos’s famous “Regret Minimization Framework” that led to founding Amazon. But Pink cautions against overuse. While anticipating regret can push us toward courage and integrity, overdoing it can trap us in paralysis and perfectionism. The key isn’t to eliminate regret but to optimize it—focusing on the regrets that matter: those tied to stability, boldness, morality, and connection.

Why This Book Matters

In an era of toxic positivity and relentless forward motion, The Power of Regret offers an antidote: reflection. It invites you to pause and ask, “What would I do differently—and what can I learn from that?” Through stories of soldiers, CEOs, parents, and ordinary people, Pink weaves a portrait of humanity that’s both scientific and deeply humane. Regret, he concludes, makes us human. It makes us better. And most importantly, it gives us hope. The goal isn’t to live with no regrets; it’s to live with our regrets wisely, letting them shape a deeper, more intentional life.

Pink takes readers on a tour of regret’s biological and cognitive foundations to show that it’s not a moral flaw—it’s a mental feature. Regret rests on two uniquely human abilities: mental time travel and imagination. You can mentally revisit the past and simulate alternate outcomes. This “counterfactual thinking,” explored by researchers like Daniel Kahneman and Amos Tversky, makes regret painful—but it’s also the brain’s way of teaching lessons for future performance.

Why We Feel Regret

In dozens of lab studies, scientists have shown that regret emerges from comparison. We measure what happened against what might have been and blame ourselves for the difference. It’s self-awareness turned inward—a sign of agency. That’s why people with brain damage to the orbitofrontal cortex can’t feel regret; it’s not self-control they lose but the ability to imagine alternatives. When regret is missing, humanity itself is diminished. Pink argues this realization flips the “no regrets” creed on its head. Lack of regret is not freedom—it’s impairment.

At Leasts and If Onlys

Pink uses Olympic athletes to illustrate how regret works in real time. After the 1992 and 2016 Games, researchers found that bronze medalists looked happier than silver ones. Why? The silver medalists stew in upward comparisons—“If only I’d gone faster.” Bronze medalists focus on downward comparisons—“At least I got a medal!” These two mental processes—If Onlys and At Leasts—reveal regret’s paradox. “At leasters” feel better but learn little. “If onlyers” suffer more but grow stronger. Pain, he concludes, is the price of progress. Just as athletes use failure to train, regret forces us to endure immediate discomfort for long-term wisdom.

Regret Makes Us Better Decision-Makers

Through experiments on negotiation and learning, Pink shows how regret recalibrates judgment. When people reflect on previous choices with remorse, they gather more information, slow down, and avoid repeating mistakes. CEOs who revisit their bad calls tend to make sounder future decisions; negotiators who replay their past missteps prepare more thoroughly next time. This pattern even appears in children. Around age seven, children gain the cognitive maturity to experience regret—and consequently become better at making smart choices. Regret is the brain’s built-in feedback loop: unpleasant to experience, indispensable to evolve.

After analyzing thousands of regrets worldwide, Pink distilled them into four “deep structure” types that transcend culture, age, and circumstance. These aren’t random mistakes; they’re signals of four universal human needs: stability, growth, morality, and love. Each core regret arises when one of these needs goes unmet—and together they sketch the outline of a good life.

Foundation Regrets: If Only I’d Done the Work

Foundation regrets are the “Ant and the Grasshopper” mistakes—skipping the planning, saving, or studying that time later punishes. Jason Drent, a successful executive who failed to save money, embodies this regret. These regrets show the lure of short-term pleasure over long-term thinking, a tendency psychologists call temporal discounting. We overvalue the present, undervalue the future, and pay the price decades later. Foundation regrets whisper, “Do the work. Start today.”

Boldness Regrets: If Only I’d Taken the Chance

Boldness regrets sting when safety wins over possibility. They’re the missed calls, the unchased dreams, the trains we never boarded—like Bruce, who met a woman on a European train but never stepped off to follow her. Over time, people regret inaction more than action, because inaction lacks closure. “What if?” echoes louder than “At least I tried.” Boldness regrets teach the need for growth: say yes, speak up, step forward, even when afraid.

Moral Regrets: If Only I’d Done the Right Thing

This category concerns our character. Whether it’s a student cheating, a spouse unfaithful, or a bully harming someone weaker, moral regrets cut deep because they betray our belief in our own goodness. Drawing on Jonathan Haidt’s “moral foundations theory,” Pink shows that across cultures, people regret harm, cheating, disloyalty, subversion, and desecration most. Beneath these sins lies a longing for integrity. Moral regrets urge, “Be good. Live up to your values.”

Connection Regrets: If Only I’d Reached Out

Connection regrets mourn the relationships that died not from conflict but neglect. Pink contrasts “closed doors” (relationships lost forever, like a friend who died before we called) with “open doors” (people we could still reconnect with but haven’t). Awkwardness, he writes, is the great barrier—yet most people who receive a reconnection attempt feel grateful, not uncomfortable. Connection regrets reveal the human need for love—romantic, familial, or platonic—and their simple lesson: reach out now, before the door closes.

After establishing that regret is universal, Pink examines how to use it. The secret lies in transforming raw emotion into insight and action. Borrowing from psychologist William James’s idea that “thinking is for doing,” Pink reframes emotion as fuel for thought. You shouldn’t ignore or wallow in regret—you should confront it to catalyze reflection and action.

Three Ways to Mismanage Emotions

Pink identifies three faulty strategies: dodging regret (denial), drowning in it (rumination), and performing it (self-pity). Avoidance breeds delusion; overindulgence breeds despair. The healthy alternative is to treat regret as data. Emotions are signals, not verdicts. Used well, they become intelligence—your heart’s feedback to your head.

The Kintsugi Metaphor

Pink likens this process to kintsugi, the Japanese art of mending broken pottery with gold. The cracks don’t ruin the bowl—they make it beautiful. Likewise, regret’s scars can enrich your life if you repair them honestly. Cyclist Mara Abbott, who lost Olympic gold by seconds, later described her heartbreak as her greatest privilege. Her crack, Pink writes, “is how the light gets in.”

Handled well, regret turns mistakes into meaning. It clarifies priorities. It reminds us that pain is information—and that the good life rarely comes unbroken.

What can you do once a regret takes hold? Pink offers two immediate strategies for regrets of action: undo it or “At Least” it. He argues that regret can be managed, if not erased, by behavioral and cognitive reframing—reducing its sting in the present so you can focus on the future.

Undo It: The Art of Apology and Action

Some regrets can be fixed through direct repair. Drawing on the Dutch TV show Het Spijt Me (“I Am Sorry”), Pink shows how apologies and amended actions restore balance. Moral and connection regrets, in particular, respond to repair—making amends, paying debts, or simply picking up the phone. Taking action releases cognitive tension; even a partial fix resets your emotional equilibrium.

At Least It: Silver Linings and Emotional Antibiotics

When undoing isn’t possible, Pink encourages finding a silver lining. Reframing with gratitude—“At least I learned,” “At least I met my spouse there,” “At least it didn’t turn out worse”—builds psychological resilience. Like antibiotics, At Leasts must be used wisely: too many breed denial, too few breed despair. The goal isn’t to erase regret but to manage it, then move forward lighter.

Building on his earlier advice, Pink presents a powerful three-part framework for lifelong learning through regret: self-disclosure, self-compassion, and self-distancing. Together, these practices help you confront regret honestly, treat yourself kindly, and extract wisdom instead of shame.

1. Self-Disclosure: Relive and Relieve

Keeping regrets secret gives them power. Sharing them—through writing, talking, or recording—diminishes their hold. Pink references James Pennebaker’s research showing that expressive writing improves both mental and physical health. As in therapy, language turns emotional chaos into cognitive clarity. Simply writing about a regret for fifteen minutes over three days can increase life satisfaction and reduce anxiety.

2. Self-Compassion: Normalize and Neutralize

Borrowing from Kristin Neff’s work, Pink argues that self-compassion beats self-criticism and self-esteem. Instead of berating yourself, treat yourself as kindly as you’d treat a friend. Recognize that mistakes are universal, not unique failures. Studies show that self-compassionate people are more resilient and more motivated to improve; they confront their errors without crumbling under them.

3. Self-Distancing: Analyze and Strategize

Finally, zoom out. Talk to yourself as if advising someone else. Use third-person language—“What should [your name] do next?”—to create emotional distance and clearer thinking. This “fly-on-the-wall” approach, validated by Ethan Kross’s research, helps people reason more wisely and calmly. Regret becomes insight; pain becomes perspective.

Pink concludes by flipping the lens forward: can we use the idea of regret to make better future choices? Yes—but carefully. “Anticipated regret,” he shows, is a potent motivator that can guide good decisions or fuel unhealthy perfectionism, depending on how you apply it.

When Anticipating Regret Helps

From Alfred Nobel rewriting his legacy to Jeff Bezos founding Amazon, the ability to foresee one’s future regret can spur meaningful action. Behavioral economists call this the “regret lottery” effect—people act to avoid the pain of a missed opportunity. Studies show that anticipating regret drives healthier behavior, from exercising and eating vegetables to getting vaccinated. Pink calls this the upside of foresight: slowing down decisions by picturing tomorrow’s “If Only.”

When Anticipating Regret Hurts

But there’s a catch. Anticipated regret can warp judgment. Thinking too hard about future disappointment makes us play it safe—choosing brand names over bargains, sticking with first instincts on tests, or refusing to switch lottery tickets for fear of “what if.” Psychologists call this the “first instinct fallacy.” Overestimating regret leads to overcautious living and chronic indecision. The goal isn’t to minimize regret everywhere—it’s to know where it matters.

The Regret Optimization Framework

Pink’s final insight is that we should optimize, not eliminate, regret. Focus your foresight on the four domains that define the good life: foundation, boldness, morality, and connection. Before a big choice, project yourself into the future and ask: “Which option will I most regret not taking?” If it concerns your health, your integrity, your growth, or your relationships—take the leap. On everything else—the lawn furniture, the microwave—don’t sweat it. Decide, move on, and reserve your energy for what truly counts.

In his coda, Pink reframes regret as the foundation of redemption. Drawing on psychologist Dan McAdams’s research on life stories, he distinguishes between contamination narratives, where life turns from good to bad, and redemption narratives, where pain leads to growth. Regret, Pink says, is the ultimate redemption story: every “I wish I hadn’t” can become “I’m glad I learned.”

Living at the Intersection of Fate and Free Will

Pink’s surveys reveal a paradox: most people believe both that they have free will and that everything happens for a reason. Instead of contradiction, he sees humanity—the coexistence of agency and acceptance. Regret lives in that space. It acknowledges what we can control and releases what we cannot. We’re both authors and actors in our own stories, scripting and performing life at once.

A Real-Life Redemption

The book closes where it began—with Cheryl Johnson, who regretted letting a cherished friendship fade. After twenty-five years, she finally reached out. Her friend replied within hours, and their reunion was warm and hopeful. “I finally got to say I made a mistake,” Cheryl told Pink, “and she said, ‘We still have a lot of years left.’” The moment distills Pink’s thesis: confronting regret opens the door to renewal.

To live without regret is to deny our humanity. To live with it wisely is to embrace growth, integrity, and connection. In the end, Pink writes, regret makes us human, regret makes us better—and regret gives us hope.