Editor's Choice

The Power of Regret: How Looking Backward Moves Us Forward

Dylan Schleicher

February 04, 2022


Daniel Pink’s new book teaches us how to embrace regret as a process to help build better lives. In doing so, we can learn to use it to cultivate self-compassion and stronger connections with others.

imagey6vnqi.pngThe Power of Regret: How Looking Backward Moves Us Forward by Daniel H. Pink, Riverhead Books 

“No regrets” has become—or perhaps has been for a long time—a popular proclamation to make. Once you start looking, as Dan Pink did, it pops up everywhere: “Embedded in songs, emblazoned on skin, and embraced by sages, the anti-regret philosophy is so self-evidently true that it’s more often asserted than argued.” Pink would like to argue otherwise, to reclaim regret from the protestations against it that are so prevalent in our popular culture. He has found that this dogma of pop-psychology amounts to a form of pseudo self-care that can, in fact, undermine our well-being and development. It is also not really possible. His new book, The Power of Regret, teaches us how to embrace regret as a process to help build better lives. In doing so, we can learn to use it to cultivate self-compassion and stronger connections with others. 

Because regret is perceived as a negative feeling, and one that has no effect on past actions or decisions, people are inclined to view it as unproductive and self-defeating, or to deny it altogether.  As Pink writes: 

Some beliefs operate quietly, like existential background music. Others become anthems for a way of living. And few credos blare more loudly than the doctrine that regret is foolish—that it wastes our time and sabotages our well-being. 

But if we see regret more accurately, as a process, then it can become very productive indeed. Because regret is more than just a feeling. It is an emotional act that requires cognitive time travel. We project ourselves backward to consider our behavior, write an alternate version of our lives in our heads based on how things would have turned out had we acted differently, use it to adjust to our present and transform our future.  

Unlike other feelings, we aren’t born with regret; it is something we learn.  

Most children don’t begin to understand regret until age six. But by age eight, they develop the ability even to anticipate regret. And by adolescence, the thinking skills necessary to experience regret have fully emerged. Regret is a marker of a healthy, maturing mind.  

I am incredibly happy to read that, because my wife and I let one of our young children do whatever they wanted on their birthday earlier this week, and they regretted—to the point of tears—wasting two hours of it on video games. We’ll have to teach our kids not to wallow in regret (something Pink’s book will help us do) but I'm happy to know it’s also a sign of a healthy, maturing mind.  

Studies on regret in adults, in which participants are presented with two scenarios and asked which would provoke a greater feeling of regret, have found that we all intuitively land on the same answer with one exception—those with cognitive disorders and brain injuries: 

In other words, the inability to feel regret—in some sense, the apotheosis of what the “no regrets” philosophy encourages—wasn’t an advantage. It was a sign of brain damage. 

One thing I don’t think Dan Pink has himself ever regretted is skimping on his research. All of his books dive deep into the available science of the subject he is writing on, and this one is no different. But, to write The Power of Regret, he also created his own body of research and data to analyze: 

Working with a large software and data analytics company, which itself contracted with firms that assemble panels of participants, we created the largest and most representative American survey on regret ever attempted—the American Regret Project. We polled 4,489 adults—whose gender, age, race, marital status, geography, income, and education level reflected the composition of the entire U.S. population. 

You can find the full version of that project online at www.danpink.com/surveyresults. But he also broadened beyond that and “collected thousands more entries worldwide in the World Regret Survey” (www.worldregretsurvey.com). What he believes he found in analyzing all the stories that came pouring in is similar to what linguists have found in studying language: that regret “has both a surface structure and a deep structure.”  

The deep structure reveals four fundamental categories of regret—foundation regrets, boldness regrets, moral regrets, and connection regrets—and he devotes a chapter to describing and pulling examples from the survey for each. Most studies in the past have put regrets into categories like family, education, or career. What Pink found is that it is more revealing to dive deeper into the individual reasons for that regret. So, to oversimplify things, think about career regrets. If we have one, it could be because we think we could have worked harder to establish a better and more stable career (foundation), or because we ceded to stability and played it safe when what we really yearned for was to take more chances and try something new (boldness), or because we cut corners and acted unethically during our career (moral), maybe even because we didn’t put ourselves out there to make more lasting personal connections in our careers or didn’t stay in touch with a colleague that became a great friend (connection).  

But the power of the book isn’t confined to what he deduced from the survey. The oversimplified, generic explanation I just provided doesn’t do justice to either the depth of his findings or the personal and often heartrending stories that came in through the survey and are shared throughout the book. Some of the stories are of circumstances I would not regret myself, but the sense of regret emanating from them is impossible not to empathize with and provides a moving impact on its own. The most common of the foundation regrets is, not surprisingly, that of connection, and the stories of people losing touch with cherished friends and loved ones through “rifts and drifts” in the relationships of their lives will hit close to home for most of us. Such stories and feelings are common and incredibly consequential. But, like all four of the foundation regrets, they become valuable when we are able to use them as an impetus for reflection and action.  

The four core regrets operate as a photographic negative of the good life. If we know what people regret the most, we can reverse that image to reveal what they value the most. 

Pink references the work of William James, who wrote that ““My thinking is first and last and always for the sake of my doing.” That is, thinking is for acting. He extends that to our emotional life to find “feeling is for thinking.” So, if feeling is for thinking, and thinking is for action, regret is one of the most powerful and instructive feelings we have, meaning it can be one of the greatest impetuses for the actions we take. On the other side of the four foundation regrets, if we process them into thinking and action, lay Stability, Growth, Goodness, and Love:  

A solid foundation. A little boldness. Basic morality. Meaningful connections. The negative emotion of regret reveals the positive path for living. 

Near the end of the book, Pink lays out “a three-step process for transforming … regrets in ways that prepare you for the future."




I’ve always had a voracious appetite for books, but have never been able to live very strictly by any of them, and have found myself woefully inadequate at following such personal improvement processes in the past. This one, however, seems doable. Even if I don’t follow that process to a T, though, one idea I know I’ll incorporate is pairing “New Year’s resolutions with Old Year’s regrets.” Being an extremely self-critical person, a trait Pink also addresses in the book and that I’m hoping to turn into greater self-compassion with his sage advice, I find that grounding any ambition with some admonition feels more proper. Overall, I am thankful to Dan Pink for the time he’s given to the topic so that we all have some time to sit with it. Whether you follow the steps yourself, or simply learn to form a new perspective on and relationship to a popularly maligned emotion, The Power of Regret is a powerful book worthy of your time.  

About Dylan Schleicher

Dylan Schleicher has been a part of Porchlight since 2003. After beginning in shipping and receiving, he moved through customer service (with some accounting on the side) before entering into his current, highly elliptical orbit of duties overseeing the marketing and editorial aspects of the company. Outside of work, you’ll find him volunteering or playing basketball at his kids’ school, catching the weekly summer concert at the Washington Park Bandshell, or strolling through one of the many other parks or green spaces around his home in Milwaukee (most likely his own gardens). He lives with his wife and two children in the Washington Heights neighborhood on Milwaukee's West Side.

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