The Power of Regret: How Looking Backward Moves Us Forward

About the Author

Daniel H. Pink is the author of the New York Times bestsellers A Whole New Mind, Drive, To Sell Is Human, and When. Pink graduated from Northwestern University and later received his Doctor of Law degree from Yale Law School, where he was editor-in-chief of the Yale Law & Policy Review. He has earned honorary doctorates from Georgetown University, the Pratt Institute, the Ringling College of Art and Design, the University of Indianapolis, and Westfield State University.

Pink worked as the special assistant to Secretary of Labor Robert Reich from 1993 to 1995 and served as chief speechwriter for Vice President Al Gore from 1995 to 1997. In 2014, Pink became the host and a co-executive producer of the National Geographic Channel social science TV series Crowd Control. Currently, he hosts a MasterClass about sales and persuasion.

Pink has worked as a contributing editor at Fast Company and Wired, and as a business columnist for The Sunday Telegraph. He has also published articles and essays in The New York Times, Harvard Business Review, The Atlantic, and Slate.

Sources: danpink.com, Wikipedia, and the “About the Author” section of the book

Our one-sentence summary

Understanding what regret is, where it comes from, and the needs it reveals helps us learn from our mistakes, take control of our decisions, and improve overall performance –bettering our enjoyment of life.

Publisher’s Summary

“No regrets.” You’ve heard people proclaim it as a philosophy of life. That’s nonsense, and even dangerous, says Daniel H. Pink in this bold and inspiring book. Everybody has regrets. They’re a fundamental part of our lives. If we reckon with them in fresh and imaginative ways, we can enlist our regrets to make smarter decisions, perform better at work and school, and deepen our sense of meaning and purpose.

In The Power of Regret, Pink draws on research in psychology, neuroscience, economics, and biology to challenge widely held assumptions about emotions and behavior. Using the largest sampling of American attitudes about regret ever conducted as well as his own World Regret Survey – which has collected regrets from more than 16,000 people in 105 countries – he identifies the four core regrets that most people have. These four regrets, Pink argues, operate as a “photographic negative” of the good life. By understanding what people regret the most, we can understand what they value most. And by allowing the simple, science-based, three-step process that he sets out, we can transform our regrets into a positive force for working smarter and living better.

With Pink’s signature blend of big ideas and practical takeaways, captivating stories and crisp humor, The Power of Regret offers an urgent and indispensable guide for a life well lived.

Source: Book jacket

Detailed Summary 

Part I – Regret Reclaimed

Chapter 1: The Life-Thwarting Nonsense of No Regrets

• People think regret is unwise. They believe it wastes time and disrupts our well-being.
  • Culture constantly sends messages about how we should forget the past and seize the future. They say a good life should be about moving forward, always in a positive manner. And they say regret only interrupts you from living your life positively.
  • While this viewpoint makes sense, feels right, and appears convincing, it’s wrong.
• Regret is healthy and an integral part of being a human. It’s valuable.
• We tend to value positive emotions so much that we forget that negative emotions serve a healthy purpose too. In fact, too much positivity can inhibit learning, which limits our potential.
• The purpose of this book is “to reclaim regret as an indispensable emotion” (p.13). This book teaches us how to use the many strengths of regret to perform better at work and school, and bring greater meaning to life.
  • Part I explains why regret matters.
  • Part II describes what people truly regret.
  • Part III offers strategies to turn regret into something positive that will help you improve your life.

Chapter 2: Why Regret Makes Us Human

• Most children don’t understand regret. Humans begin to grasp the concept at around the age of six. We begin to anticipate it at approximately eight years old. By adolescence, we fully develop the thinking skills necessary to experience
• Although it’s easy to recognize, regret is difficult to define. Some definitions include:
  • “The unpleasant feeling associated with some action or inaction a person has taken which has led to a state of affairs that he or she wishes were different.” (p.17)
  • “The comparison between the actual outcome and that outcome that would have occurred had the decision maker made a different choice.” (p.17)
  • “A feeling of unpleasure associated with a thought of the past, together with the identification of an object and the announcement of an inclination to behave in a certain way in the future.” (p.17)
• Regret is better understood as an emotional process inherent to humans that emerges because of two unique abilities:
  • We are capable of mentally visiting the past and the future.
  • We can picture situations and tell stories of things that never happened.
• What distinguishes regret from other negative emotions such as sadness or disappointment are two mental faculties we can all engage in:
  • We can compare and contrast what currently is with what could’ve been.
  • We can assess blame and assign it to ourselves.
• Regret is human. Beyond that, it makes us better.

Chapter 3: At Leasts and If Onlys

• The human ability to mentally travel through time and picture scenarios that never happened enables what researchers call counterfactual thinking.
• In several studies, researchers found that Olympic athletes who finished in third place were significantly happier than those who finished in second place. They concluded that what drove this unexpected reaction was counterfactual thinking.
  • Counterfactuals can point in two directions:
    • Downward counterfactuals happen when we think about how an alternative scenario could’ve been worse: At Leasts.
    • Upward counterfactuals happen when we imagine how things could’ve gone better: If Onlys.
  • Bronze medalists think “at least…” while silver medalists think “if only…”
  • At Leasts lead to comfort and consolation; If Onlys result in discomfort and distress.
• Since humans naturally seek pleasure and avoid pain, it would appear that humans favor At Leasts over If Onlys. However, when researchers tracked people’s thoughts by asking them to keep a diary, If Onlys outnumbered At Leasts.
  • Thoughts about the past that make us feel good are rarer than thoughts about the past that make us feel bad. Is this a way in which humans self-sabotage? No.
    • At Least counterfactuals preserve our feelings at the moment but rarely do they enhance our decisions or performance in the future.
    • If Only counterfactuals hurt our feelings now but can improve our lives later.
    • Regret is the ultimate upward counterfactual, the ultimate If Only.
    • Regret’s purpose is to make us feel bad today so that we can do better tomorrow.

Chapter 4: Why Regret Makes Us Better

• We all have been in a situation where we made a bad choice, and instead of counting our losses and switching tactics, we decided to continue working and investing time in our lost cause. This phenomenon is called escalation of commitment to a failing course of action, and it is a common cognitive bias that often contaminates our decisions. But regret can fix our tendency to do this.
• There are three benefits of regret:
  1. Regret can improve our decision-making skills.
     • Regret emphasizes the mistakes we have made so that, should a similar situation arise, we don’t make the same mistakes again.
  2. Regret can boost our performance.
     • Getting people to think counterfactually, both about personal and vicarious experiences, leads people to think about future decisions more carefully.
  3. Regret can deepen meaning.
     • People who think counterfactually about their pivotal moments in life give greater meaning to those experiences.

• Three viewpoints explain emotions. Two of these are dangerous and one is ideal.
  1. Feelings are for ignoring.
     • This viewpoint is dangerous because ignoring your emotions not only does not dissipate them, but can lead to physical problems including headaches, intestinal problems, and autoimmune disorders.
  2. Feelings are for feeling.
     • This viewpoint suggests that because our feelings are the essence of our being, we should always express them. This view is even more dangerous than ignoring your emotions because it can lead to rumination, depression, anxiety, and PTSD.
  3. Feelings are for thinking.
     • Don’t dodge emotions. Don’t wallow in your emotions. Confront them. Use your emotions as a catalyst for future behavior. There’s a saying that goes, “Thinking is for doing.” If that’s the case, then feelings can help us think.
• Regret that hurts deeply but dissolves quickly leads to more effective problem-solving and sturdier emotional health.

Part II – Regret Revealed

Chapter 5: Regret on the Surface

• In the 1980s, studies concluded that education (e.g., not taking it seriously, choosing the wrong courses in college, not finishing school, etc.) was the most common area of regret.
• In the 1990s, studies again found that education was the most common area of regret among different generations and genders.
  • The researchers concluded that education was the most common regret type because it is open to continual modification.
  • They argued that opportunity and availability give way to regret.
  • However, they soon discovered that both their “what” and their “why” was faulty.
• Because the samples were not representative of the general population (most participants were college students), in 2011, they reran the survey with a national representative sample. They found no single category captured more than 20% of the public mind.
  • Romance regrets were the most common at 19%, followed by family at 17%, and education and career at 14%.
  • Women were more likely than men to have romance and family regrets.
  • People with the least formal education were more likely to have education regrets.
  • Single, unattached people harbored more romance regrets.
  • Based on these findings, the researchers concluded that regret hinged on opportunity. But, they argued, it was not the abundance of opportunity that led to regret. It was missed
• More recently, Daniel Pink created the largest and most representative survey on regret ever attempted: the American Regret Project.
  • Over 4,480 adults participated in this study. Their gender, age, race, marital status, geography, income, and education level was reflective of the entire US population.
  • In this survey, family took the top spot with 22% of people voicing regret in this area. Partner choice was the second most common category. Education, career, and finance were the next three most common, all with similar percentages. Health and friends were the least common of the categories explored.
  • The conclusion was that American regrets span a wide range of domains.
• Unsatisfied with his conclusion, Pink launched the World Regret Survey and discovered that he was looking for his answers in the wrong place.

Chapter 6: The Four Core Regrets

• In his survey, Pink read several entries. For instance, in one case, a man named Kevin told him about how he had procrastinated so much that, despite his good college grades, he failed the MCAT and didn’t get into med school. He also reviewed the story of John, who got married and decided to work instead of going to grad school.
• Pink realized something: Both men regretted not making wiser education and career choices. On the surface, their regrets appeared similar. But, below the surface, the roots of the regrets diverged:
  • Kevin regretted not taking his future seriously; i.e., failing to be conscientious.
  • John regretted not taking a risk; i.e., failing to be bold.
• In another set of entries, Pink noticed the opposite pattern. A man said that his greatest regret was being unfaithful to his wife. Another man said he regretted bullying kids when he was young. And a woman wrote about how she regretted cheating in a student election.
• These regrets are about different realms in life: marriage, bullying, and cheating. But they are not that different; they all involve a moral breach.
• While analyzing data, Pink discovered that regret has a surface structure and a deep structure. What’s visible and easy to describe –the realms of life such as family, education, work –is less significant than the hidden human motivation and aspiration lying beneath.
• As Pink read through entries, he identified common words and phrases that did not correlate to age, gender, location, or the topic of the issue.
• After further analyses, Pink was able to define the four core regrets:

1. 1. Foundation Regrets. Education, finance, and health regrets are expressions of the same core: failure to be responsible, conscientious, and prudent. When we make irresponsible choices, and then we have to deal with consequences, we feel regret.
   2. Boldness Regrets. As we age, we are more likely to regret what we didn’t do than what we did. What haunts us is the inaction itself, the forgone opportunities.
   3. Moral Regrets. Most of us want to be good people. But sometimes, we fall under the temptation of bad choices. The realm in which they occur – deceiving a spouse or cheating on a test – is often not as significant as the act itself. When we compromise our values and beliefs, we can feel persistent regret.
   4. Connection Regrets. Connection regrets arise when we neglect the people whom we love and who loves us. When those relationships fray, we feel loss and regret.

Chapter 7: Foundation Regrets

• Foundation regrets arise from our failures of forethought, prudence, and conscientiousness.
  • Many times, we make choices that require a short-term sacrifice, but we understand that it is in the service of a long-term payoff. Other times, we make choices that require little diligence in the now but that are very costly in the future.
  • Foundation regrets sound like this: “If only I had done the work.”
• Temporal discounting refers to when we overvalue the present and undervalue the future.
  • Ernest Hemingway’s 1926 novel The Sun Also Rises has a conversation between two characters where one asks, “How did you go bankrupt?” “Two ways,” the other replies, “gradually and then suddenly.”
  • This is how people discover foundation regrets. Our brains lure us into valuing the now too much and the later too little. They prevent us from understanding the compounding effect of our choices.
• Foundation regrets are both difficult to avoid and difficult to undo.
• Foundation regrets are more common among older people because weaknesses in our foundation take time to appear.
• The solution to this type of regret is quite simple. Taking from a Chinese proverb: The best time to plant a tree is twenty years ago. The second best time is today.
• Foundation regrets are trickier than other types of regrets because of responsibility.
  • The fundamental attribution error refers to when we try to explain behavior solely based on personality and disposition and don’t consider the situation or context. For example, when a driver cuts us off on the highway, we tend to assume that the person is irresponsible and rude instead of considering the possibility that he or she might be rushing to the hospital.
  • Because of this bias, sometimes we attribute failures to personal choices when they are due, at least in part, to situations out of our control.
  • To fix and avoid foundation regrets, we not only need to change the person. Sometimes we also need to reconfigure the situation, setting, or environment.
• Foundation regrets reveal a need for stability. We need a basic infrastructure of educational, financial, and physical well-being to reduce psychological uncertainty.
• The lesson we need to learn from this type of regret is that we need to think ahead, do the work, and start today.

Chapter 8: Boldness Regrets

• Boldness regrets come from us failing to take full advantage of an opportunity.
  • With boldness regrets, we choose to play it safe.
  • Boldness regrets sound like this: “If only I had taken that risk.”
• Even though boldness regrets can happen in many of the realms of life, in his research Pink found a few common themes:
  • People regret not being bold, speaking up, voicing their thoughts. They regret being shy and not standing up for themselves.
  • People also regret the famous “What if?” In other words, they regret inaction – especially in the long term.
    • This regret stems from not knowing what happened next. When we don’t act, we can only speculate about the “What if?” And we always think the alternative would have been better.
    • Boldness regrets are particularly pervasive in the realm of romance.
  • At the heart of boldness regrets is also the possibility of growth.
    • In the realm of careers and professional development, boldness regrets occur when people keep the same job, even if they don’t like it, for fear of failure. A lot of people also regret not starting a business.
    • Boldness regrets are also common among people who decided not to travel when given the opportunity.
  • Another common theme was “not being true to myself.” People deeply regret denying themselves the potential to live fully by hiding their true personality or identity.
• Boldness regrets reveal a need for human growth, to expand as a person, enjoy the world, and experience life.
• The lesson we need to learn from boldness regrets is that we need to speak up, ask him/her out, take that trip, start that business, and take the risk.

Chapter 9: Moral Regrets

• Moral regrets make up the smallest of the four categories, representing only about 10% of the total. But these regrets often ache the most and last the longest
  • Compared to the other types of regrets, moral regrets involve a wider set of values. They are characterized by choosing what our conscience later tells us was the wrong path. Often, we hurt others.
  • Moral regrets sound like this: “If only I’d done the right thing.”
• To understand moral regrets, we need to understand morality.
  • Moral foundation theory suggests that beliefs about morality stem from the survival of the human species:
    • Care vs. harm – We have evolved to perceive those who defend the vulnerable as kind and those who harm them as cruel.
    • Fairness vs. cheating – Survival of the species also depends on cooperation: we value those we can trust and disdain those who breach our trust.
    • Loyalty vs. disloyalty – Survival of the species also depends on cohesiveness in a group. That’s why we value loyalty and revile forsaking our tribe.
    • Authority vs. subversion – Social hierarchies help establish roles and protection. That’s why deference and obedience toward authority figures (e.g., parents) are seen as virtuous.
    • Purity vs. desecration – We all have different views about life, marriage, pornography, euthanasia, and abortion.
• Taking from this theory and based on his research, Pink proposed the five regretted sins:

1. 1. Harm: This is the most common type of moral regret.
      • The most common harm was bullying. Even being a bystander to bullying was enough to trigger regret for people who did not stand up for the victim.
      • People also described insulting others, ghosting romantic interests, and threatening neighbors as a harm regret.
   2. Cheating: This is the second most common type of moral regret.
      • In this case, most people and cultures agree that we should tell the truth, keep our promises, and follow the rules.
      • This category considers all forms of cheating, including taking things that aren’t ours and academic dishonesty.
      • Respondents regret not just the pain inflicted on others but the trust that they shattered.
   3. Disloyalty: Many people regret not being team players. Especially in the case of American participants, many regretted not joining the military.
   4. Subversion: A handful of people regretted dishonoring their parents or being disrespectful to teachers and other authority figures.
   5. Desecration: Regrets about violating sanctity were not particularly common, but they were among the most emotionally intense. For instance, many people reported regretting having an abortion.

• Moral regrets reveal a need for goodness.
• The lesson we need to learn from moral regrets is, when in doubt, do the right thing.

Chapter 10: Connection Regrets

• Connection regrets are the largest category of human regret. They arise from relationships that disappeared.
  • Connection regrets sound like this: “If only I’d reached out.”
• There are two types of regrets under this category:
  • Those that lead to closed doors (that teach us valuable lessons).
  • Those that still have open doors (which means we can still make amends).
• There are also two types of ways in which relationships end: via drifts and via rifts.
  • Rifts usually begin with an incident, e.g., an insult or a betrayal. They leave the parties resentful and antagonistic.
  • Drifts often lack a discernible reason for the relationship’s end.
• Rifts are more dramatic, but drifts are more common.
  • The reason why many people let relationships drift is that reaching out seems awkward and becomes uncomfortable.
  • Pluralistic ignorance is a phenomenon in which we mistakenly assume our beliefs differ vastly from everyone else’s. Our concerns about the awkwardness of reconnecting with someone conform to this pattern.
  • Research, however, shows that people do not tend to perceive others who reach out as awkward, but instead appreciate it.
• One of the most important long-term studies in the history of psychology found that it is not money or fame, but close relationships that keep people happy throughout their lives. Close ties keep people healthy (physically and mentally) and better predict happiness and success (compared to social class, IQ, and even genes).
• When it comes to restoring relationships, it is always better to err on the side of reaching out. You will get over awkwardness, but if you don’t reach out, the relationship is definitely lost forever.
• Connection regrets reveal a need for love.
• The lessons we need to learn from connection regrets are:
  • Closed doors tell us we need to do better next time.
  • Open doors tell us we need to do something now. Call that someone, visit them, say what you feel, push past the awkwardness and reach out.

Chapter 11: Opportunity and Obligation

• By understanding what people regret the most, we can find out what they value the most.
• So, what do we all ultimately want and need? The table below summarizes the deep structure of regret and provides an answer.

• Self-discrepancy theory (proposed by Higgins in 1987), suggests we have three selves:

1. Actual self refers to the attributes that we currently possess; who we really are.
2. Ideal self refers to the self we believe we could be; our hopes, wishes, and dreams.
3. Ought self refers to the self we believe we should be; our duties and responsibilities.

• Perceived discrepancies between these three selves guide our behavior.
• A study performed in 2018 concluded that people regret more their failures to live up to their ideal selves than to their ought selves. This is probably because of the distinct emotional consequences of these two forms of regret:
  • Discrepancies between our actual and ought selves make us restless and prompt us to act – to fulfill our obligations.
  • Discrepancies between our actual and ideal selves make us dejected, often not motivating us to act or pursue opportunities.
• The four core regrets involve opportunity, obligation, or both.
  • Boldness regrets are opportunities we didn’t seize.
  • Foundation regrets are opportunities that we didn’t pursue.
  • Connection regrets are a mix; they involve opportunities for friendship that we didn’t follow through on and obligations with family that we neglected.
  • Moral regrets are about obligations that we didn’t meet.
• In the American Regret Project survey, among the many differences in demographics, the most notorious difference between groups was based on age; the older the person, the more the inaction regrets weighed on them.
• “We regret forgone opportunities more often than unfulfilled obligations. However, a wholly realized life involves a mix of both dreams and duties” (p. 155).

Part III – Regret Remade

Chapter 12: Undoing and At Leasting

• You can use action regrets to your advantage.
• The first thing to do is change your situation for the better. Begin by asking yourself, “Can I make amends?” and, “Can I fix the mistake?”
• If you can’t change your situation, reframe it into an “At least.”
  • While an “At least” viewpoint will not affect your future or alter your behavior, it will help you reassess the present. You can turn regret into relief.
  • Ask yourself, “How could things have turned out worse?” and, “Is there a silver lining?” Then, complete the sentence “At least…” 

Chapter 13: Disclosure, Compassion, and Distance,

• The optimal reaction to a regret is improving the future. So instead of ignoring or wallowing in the negative emotion, remember to think. Then do.
• Follow these steps to make sure you learn the lesson that regret is trying to teach you:
• Step 1 – Self-Disclosure: Relive and Relieve
  • Research suggests disclosing our thoughts and feelings, whether by telling others or privately writing about them, leads to positive physical and mental health outcomes.
  • By sharing our regrets, we are forced to organize our thoughts. We move the experience from the emotional realm into the cognitive domain. Such a process helps us analyze our situation and mistakes, free of emotional bias, and make wiser decisions.
• Step 2 –Self-Compassion: Normalize and Neutralize
  • It was once thought that self-criticizing helped improve our performance. Then psychology experts proposed another avenue: boosting your self-esteem. However, the most recent research suggests that neither of these approaches are effective, as overusing these strategies leads dangerous consequences.
    • Self-criticizing may cause excessive rumination and hopelessness.
    • Boosting your self-esteem can foster narcissism and diminish empathy. And, because it depends on comparisons, it leads to the denigration of others.
  • The best way to improve performance based on regret is self-compassion. We need to be capable of treating ourselves with the same warmth and kindness that we would offer another person in our position or situation.
  • Self-compassion is something we can learn by practicing, simply recognizing that nobody is perfect and that making mistakes is part of life. We can learn from our mistakes, but first we need to normalize committing them.
• Step 3 – Self-Distancing: Analyze and Strategize
  • Self-distancing helps examine your regret dispassionately. This way you can learn from your mistake without feeling shame.
  • You can distance yourself from your regrets in three different ways:
    • Self-distance through space: view the scene from an objective perspective.
    • Self-distance through time: use the same strategies that lead to regret. Mentally visit the future and analyze your regret retrospectively.
    • Self-distance through language: write about your situation using the third-person pronouns.
  • The sequence of these three steps will help transform regret into stability, future achievement, and purpose.

Chapter 14: Anticipating Regret

• Research shows that we tend to find the pain of losing something greater than the pleasure of gaining the same thing. In the same way, when we anticipate regret, the pain outweighs the potential gain of the given alternative.
• Anticipating regret can help us make wiser choices. When in doubt, ask yourself, “Will I regret this decision in the future?” By picturing the pain of regret, we can force ourselves to decide better.
• However, constantly anticipating regret is also dangerous. We often overestimate how negative we will feel and underestimate our ability to cope. Continually anticipating regret is like buying emotional insurance that we don’t need.
  • Anticipating regret can make us turn away from the best decision too. That’s because minimizing regret is not the same as minimizing risk.
  • If we focus too much on what we will regret, we can become incapable of making a decision. We can also become accustomed to the idea that our choice was wrong and that we will never be pleased with any of our decisions.
  • In other words, constantly anticipating regret can become unhealthy.
• How can we get the benefits of anticipated regret without making it maladaptive?
  • The Regret Optimization Framework holds that we should only anticipate regret on matters that pertain to the four core regrets: foundation, boldness, moral, and connection regrets. Outside these four forms of regret, it is not worth anticipating it.

Coda. Regret and Redemption

• Three out of four Americans in Pink’s survey reported believing in the ideas of 1) free will and 2) that things happen for a reason.
• While these two notions appear to contradict each other, regret allows us to understand that we are both actors in and authors of the story of our lives. Regret lets us control the narrative.
• Remember, regret makes you human. It makes you better. And it should give you hope.