The Power of Regret by Daniel Pink – Here are my six lessons and takeaways

Pink, Power of Regret• “Though we would like to live without regrets, and sometimes proudly insist that we have none, this is not really possible, if only because we are mortal.” James Baldwin, 1967
• This is a book about regret—the stomach-churning feeling that the present would be better and the future brighter if only you hadn’t chosen so poorly, decided so wrongly, or acted so stupidly in the past. Over the next thirteen chapters, I hope you’ll see regret in a fresh and more accurate light, and learn to enlist its shape-shifting powers as a force for good.  
• The purpose of this book is to reclaim regret as an indispensable emotion—and to show you how to use its many strengths to make better decisions, perform better at work and school, and bring greater meaning to your life.
• How to build that life by transforming your existing regrets and anticipating your future regrets is the subject of the rest of this book.
• How often do you look back on your life and wish you had done things differently?
• Just as foundation regrets can be defined with a well-worn fable, one response to them is contained in a hoary Chinese proverb: The best time to plant a tree is twenty years ago. The second-best time is today.
Daniel H. Pink, The Power of Regret:  How Looking Backward Moves Us Forward

{“I love the idea that regrets serve an important function in our lives.” – a radio host who interviewed Daniel Pink}


If you have never done anything wrong – never made a mistake, or done something genuinely wrong (morally wrong) — or if you have never failed to take full advantage of a good opportunity…then read no further.  This book is not for you.

But, if you are like the rest of us – in other words, human, like the rest of us – you have some regrets in your life.  Therefore, this is a book to read!  Pretty soon.

I presented my synopsis of the new Daniel Pink book, The Power of Regret:  How Looking Backward Moves Us Forward, at the March, 2022 First Friday Book Synopsis.  I am cautious about throwing around the phrase “this is a life-changing book.”  (That list is really short; Man’s Search for Meaning by Viktor Frankl; and …um… maybe The Road Less Traveled by M. Scott Peck. Maybe).  But, this book is at least a life-enhancing book.  I found it well-researched, substantive, and helpful; useful; somewhat challenging and comforting at the same time.

Daniel H. Pink is the author of several provocative, bestselling books about business, work, creativity, and behavior. Author of:  A Whole New Mind; Drive; The Surprising Truth of What Motivates Us; To Sell is Human; When: The Scientific Secrets of Perfect Timing.  I have presented synopses of all of these books, most at the First Friday Book Synopsis.  Now I have added The Power of Regret to the list.

Mr. Pink is a graduate of law school, a former speech writer, but mainly… a curious mind, a thorough researcher, and a clear writer.  His books are not only good; they are good reads.  (That is not always the case, by the way).

In my synopses, I always ask: What is the point of this book?.  Here it is for this book:  You have (likely) done things you regret.; things that caused harm. You have (likely) not taken advantage of opportunities, and you regret these missed opportunities.  What can you learn from these regrets going forward? This book can help.

And I ask why is this book worth our time?  Here are my three reasons for this book:

#1 – This book provides a big picture look at why humans regret past actions and missed opportunities.
#2 – This book is filled with definitions, studies, theories, from serious researchers. In other words, regret is quite an area of study.
#3 – This book has life lessons, and business work-life lessons, and relationship lessons.  In other words, you likely need this book, in one, or more, areas of your life.

{• A word to my business books audience:

  • This is not a book about business issues; but, of course it is. It is about regrets in life, including regrets in business…
  • Regretting actions taken, &
  • Regretting inaction – actions that could have been taken}

I always include a few pages of Quotes and Excerpts from the book – the “best of” Randy’s highlighted Passages. Here are quite a few of the best of the best from this book:

• (re. those who say we should have no regrets…)  It is dead wrong. …What they are proposing is—forgive the terminology, but the next word is carefully chosen—bullshit.
• Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human. Regret is also valuable. It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up.
• These seventy years of research distill to two simple yet urgent conclusions: Regret makes us human. Regret makes us better.
• In short, people without regrets aren’t paragons of psychological health. They are often people who are seriously ill
• If Onlys outnumber At Leasts in people’s lives—often by a wide margin.
• The First Law of Holes: “When you find yourself in a hole, stop digging.”  …We often compound bad choices by continuing to invest time, money, and effort in losing causes instead of stanching our losses and switching tactics
• The very act of contemplating what they hadn’t done previously widened the possibilities of what they could do next and provided a script for future interactions.
• When we handle it properly, regret can make us better. Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning. The problem, though, is that we often don’t handle it properly.
• Blocked emotions, writes one therapist, can even lead to “physical problems like heart disease, intestinal problems, headaches, insomnia and autoimmune disorders.”
• The key is to use regret to catalyze a chain reaction: the heart signals the head, the head initiates action. …Productive regrets aggravate, then activate. Your response determines your result.
• Over time we are much more likely to regret the chances we didn’t take than the chances we did. What haunts us is the inaction itself.
• “How did you go bankrupt?” American Bill Gorton asks him. “Two ways,” Campbell replies. “Gradually and then suddenly.”
• Our brains therefore play a double trick on us. They entice us into valuing the now too much and the later too little.
• One of the most prevalent cognitive biases—in some ways the über-bias—is called the “fundamental attribution error.” When people, especially Westerners, try to explain someone’s behavior, we too often attribute the behavior to the person’s personality and disposition rather than to the person’s situation and context.
• Yet almost nobody in either the quantitative or qualitative regret surveys described excesses of extroversion, while many lamented tilting toward the other side of the scale.
• Many boldness regrets reflect a desire to grow not for any instrumental reasons but because of the inherent value of growth itself.
• Boldness regrets are often about exploration. And some of the most significant exploration, respondents said, is inward. Authenticity requires boldness. And when authenticity is thwarted, so is growth. …“Not being true to myself.”
• All deep structure regrets reveal a need and yield a lesson. With 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. The lesson is plain: Speak up. Ask him out. Take that trip. Start that business. Step off the train.
• THE FIVE REGRETTED SINS — Deceit. Infidelity. Theft. Betrayal. Sacrilege.
• People of all political persuasions agree: hurting someone who’s not provoking us is wrong.
We should tell the truth, keep our promises, and play by the agreed-upon rules.
• A 2012 study by Mike Morrison, Kai Epstude, and Neal Roese concluded that regrets about social relationships are felt more deeply than other types of regrets because they threaten our sense of belonging. …When our connections to others tatter or disintegrate, we suffer. And when it’s our fault, we suffer even more.
• “The need to belong,” they wrote, “is not just a fundamental human motive but a fundamental component of regret.”
• They were mistaken on both fronts. Those who initiated conversations found it easier to do than they expected. They enjoyed their commute more than control group participants, who remained to themselves. And the strangers with whom they spoke were not put off. They enjoyed the conversations just as much.
• In the end, the problem we contend with as people is remarkably simple. What give our lives significance and satisfaction are meaningful relationships. But when those relationships come apart, whether by intent or inattention, what stands in the way of bringing them back together are feelings of awkwardness. …So, this simple problem has an even simpler solution. Shove aside the awkwardness. “You’re almost always better off to err on the side of showing up. And if it’s awkward, then it’s awkward and you’ll live. It’ll be fine. But if you don’t show up, it’s lost forever.”
• Our actual self is the bundle of attributes that we currently possess. Our ideal self is the self we believe we could be — our hopes, wishes, and dreams. And our ought self is the self we believe we should be — our duties, commitments, and responsibilities. What fuels our behavior and directs which goals we pursue, Higgins argued, are discrepancies between these three selves.
• A life of obligation and no opportunity is crimped. A life of opportunity and no obligation is hollow. A life that fuses opportunity and obligation is true.
• But the evidence shows that self-disclosure builds affinity much more often than it triggers judgment.
• We all need some baseline level of self-esteem to survive today and flourish tomorrow.

And, in my synopses, I look for key points and main arguments in the books I present.  Here are quite a few from this book: 

  The Deep Structure of Regret  
  What it sounds like The human need it reveals
Foundation If only I’d done the work Stability
Boldness If only I’d taken the risk Growth
Moral If only I’d done the right thing Goodness
Connection If only I’d reached out Love 
  • A few regret-related stories
  • Edith Piaf, 1960, and “Non, rien de rien. Non, je ne regrette rien.”
  • “No, nothing at all. No, I regret nothing at all.”
  • (“Did you know that she [Edith Piaf] died destitute?” Mayo asks me. — As she lay in bed, life about to slip from her battered forty-seven-year-old body, her final words were, “Every damn thing you do in this life you have to pay for.”  Does that sound like a person with no regrets?)
  • Win the Gold Medal, or the Bronze Medal, and you will be happy; the Silver Medal will just about do you in…
  • The athletes who finished third appeared significantly happier than those who finished second.
  • About the American Regret Project – Pink’s own research, with thousands of participants, on what people regret; and how it has hurt them, helped them, shaped them…
  • We asked people to place their regret into one of eight categories: career, family (parents, children, grandchildren), partners (spouses, significant others), education, health, finances, friends, something else.

{• Thinking about C. S. Lewis: Mere Christianity – “right and wrong as clue to meaning of universe.”

  • When it comes to harming others for no reason or lying, cheating, and stealing, people of all backgrounds and beliefs generally concur on what’s moral.
  • In other words…we have done things that are wrong. We regret that. We have failed to do things that we “should” have done. We regret that. – (sins of omission; sins of commission)}. 
  • What is regret?
  • “Regret is created by a comparison between the actual outcome and that outcome that would have occurred had the decision maker made a different choice,” say the management theorists.
  • If the precise definition feels elusive, the reason is revealing: regret is better understood less as a thing and more as a process.
  • And, regret requires the individual to have “agency” – disappointment (the tornado hit my house) is not regret (“I wish I had finished my dissertation…”).
  • Remember that what distinguishes regret from disappointment is personal responsibility. 
  • Think about a few categories:
  • 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.
  • People reported more harm-related moral regrets than any other kind. And the most common harm was bullying. Even decades later, hundreds of respondents deeply regretted mistreating their peers.
  • Fairness/cheating
  • Loyalty/disloyalty
  • Authority/subversion
  • Purity/desecration
  • A word about what is moral…
  • When it comes to harming others for no reason or lying, cheating, and stealing, people of all backgrounds and beliefs generally concur on what’s moral.
  • All involve a moral breach. At a moment in their lives now stamped in memory, all three faced a choice: Honor their principles or betray them?
  • Our biggest regrets:
  • what we do not do (#1 for a long time; get enough education; take my education seriously)
  • Education—both “missed educational opportunities” and “bad educational choice”—came out on top. (Personal relationships—“ missed romantic opportunity” and “unwise romantic adventure”—finished next.) 
  • The four categories of regret:
  • Nearly all regrets fall into four core categories—foundation regrets, boldness regrets, moralregrets, and connection regrets.
  • 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. These regrets ache the most and last the longest.
  • Connection regrets are the largest category in the deep structure of human regret. They arise from relationships that have come undone or that remain incomplete. Some relationships fray. Others rip. A few were inadequately stitched from the beginning. But in every case, these regrets share a common plotline. A relationship that was once intact, or that ought to have been intact, no longer is.
  • Rifts and Drifts… — Rifts usually begin with a catalyzing incident. …Drifts follow a muddier narrative. They often lack a discernible beginning, middle, or end. They happen almost imperceptibly. — Rifts are more dramatic. But drifts are more common. 
  • Note: boldness regrets are especially prevalent in the work life…
  • The world of work, which most of us inhabit for more than half our waking hours, was especially fertile soil for these types of regrets.
  • I regret not having the courage to be more bold earlier in my career and caring too much what other people thought of me. 
  • At leasts and if onlys…
  • “at least I won a medal” vs. If only I had done this one tiny thing, I would have won the Gold medal.”
  • At Leasts make us feel better. “At least I ended up with a medal—unlike that American rider who blew it in the final seconds of the race and never reached the podium.” At Leasts deliver comfort and consolation. …If Onlys, by contrast, make us feel worse. If Onlys deliver discomfort and distress.
  • BUT! BUT! – People in the narrow-miss If Only group systematically outperformed those in the narrow-win At Least group in the long run. The researchers concluded that it was the setback itself that supplied the fuel. The near miss likely prompted regret, which spurred reflection, which revised strategy, which improved performance. 
  • 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.
  • Not who you are; but what you did, or did not do
  • For example, framing regret as a judgment of our underlying character—who we are—can be destructive. Framing it as an evaluation of a particular behavior in a particular situation—what we did—can be instructive. …Ample research shows that people who accept, rather than judge, their negative experiences end up faring better.
  • Pay attention to this: what you did, or did not do, long ago can impact you…
  • and regrets resulting from wrong, immoral, and harmful actions; and regrets from failing to jump at opportunities; are…universal realities…
  • in other words, many “good” people have done some bad things… the issue is, what now; what next?!
  • Regrets of action and regrets of inaction:
  • The difference between regrets of action and regrets of inaction—between regretting what we did and regretting what we didn’t do.
  • For action regrets, your initial goal should be to change the immediate situation for the better. 
  • What to do:
  • Gillian Ku, now of London Business School, found that getting people to think about a previous escalation of commitment, and then to regret it, decreased their likelihood of making the error again.
  • Linger on a regret; learn from it! BUT, do not linger too long…
    • To be sure, regret doesn’t always elevate performance. Lingering on a regret for too long, or replaying the failure over and over in your head, can have the opposite effect.
  • Excessive regret is linked to an array of mental health problems—most prominently depression and anxiety, but also post-traumatic stress disorder.
  • DO BETTER! – learn from your regret(s) to do better!
  • Hurting others is so unequivocally wrong that many people seek to channel the regret into more respectable future behavior.
  • “I’ve done badly by people in the past and I want to do right by people.”
  • Step One – Undo it. – (Make amends – learn to truly/genuinely apologize).
  • Step 2 – At least it. – (Pink: Going to law school was a mistake—but at least I met my wife).


  • The first step in reckoning with all regrets, whether regrets of action or inaction, is self-disclosure.
  • 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.
  • “Self-compassion appears to orient people to embrace their regret,” …may afford people the opportunity to discover avenues for personal improvement.”
  • Imagine your best friend is confronting the same regret that you’re dealing with. What is the lesson that the regret teaches them? What would you tell them to do next? 
  • Seven Techniques you won’t regret
  • Start a regret circle
  • Create a failure résumé.
  • Study self-compassion.
  • Pair New Year’s resolutions with Old Year’s regrets.
  • Mentally subtract positive events.
  • Participate in the World Regret Survey.
  • Adopt a journey mindset.
  • Maybe…don’t be a maximizer…
  • people pursued ideal standards (the maximizers) and which more often selected whatever met some threshold of acceptability (the satisficers.) Most maximizers were miserable. …“maximizers’ increased sensitivity to regret—both experienced and anticipated.” Maximizers regretted everything at every stage. Before they made their choices. After they made their choices. While they made their choices. Whatever the situation, they always imagined the possibilities of something better if only they had acted.
  • And here are my six lessons and takeaways:

#1 – You will do something you regret. You will fail to do something that you wish you had done; and you will regret it. What now? — Ask, “what now?”
#2 – Practice self-compassion. But, when you have wronged someone, make amends, with genuine apology.  AND, determine, to learn from this wrong action.
#3 – When you have missed an opportunity; ask yourself: “How can I set myself up to not miss my next opportunity?”
#4 – Connect with people with a little more (a lot more) boldness.
#5 — Reconnect.  If you have let someone (friend; family) drift away, reconnect.
#6 – Determine to learn from your regrets!

In my view, and experience, there are very few books that are actually life-changing.  A few more are life-enhancing.  This is such a book. Read this book:  think about what you regret.  And maybe, his suggestions can help you allow your regret to serve a vital function; helping make your tomorrow a better tomorrow.


My synopsis, with the audio recording of my presentation, and my comprehensive, multi-page handout, will be available soon on this web site.  Click here for our newest additions.

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