The Power of Regret by Daniel H. Pink

"The world needs this book." --Brené Brown, Ph.D., New York Times bestselling author of Dare to Lead and Atlas of the Heart

As featured in The Wall Street Journal and The Washington Post
Named a Must Read of 2022 by Forbes, Newsweek, and Goodreads

From the #1 New York Times-bestselling author of When and Drive, a new book about the transforming power of our most misunderstood yet potentially most valuable emotion: regret.

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Everybody has regrets, Daniel H. Pink explains in The Power of Regret. They're a universal and healthy part of being human. And understanding how regret works can help us make smarter decisions, perform better at work and school, and bring greater meaning to our lives.

Drawing on research in social psychology, neuroscience, and biology, Pink debunks the myth of the "no regrets" philosophy of life. And 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 15,000 people in 105 countries--he lays out the four core regrets that each of us has. These deep regrets offer compelling insights into how we live and how we can find a better path forward.

As he did in his bestsellers Drive, When, and A Whole New Mind, Pink lays out a dynamic new way of thinking about regret and frames his ideas in ways that are clear, accessible, and pragmatic. Packed with true stories of people's regrets as well as practical takeaways for reimagining regret as a positive force, The Power of Regret shows how we can live richer, more engaged lives.

I enjoy Daniel Pink’s work. I found When: The Scientific Secrets of Perfect Timing to be overall a little fluffy — not nearly enough science to back it up — but liked his mix of conversational and authoritative tone. I went down a habits rabbit hole in late 2019, and that one made the list. I’m glad that I read it, although perhaps from the library as it was a one-and-done read for me.

I'd rather read a heavy neuroscience book than a fluffy self-help one, even about the same topic, because I tend to want to know why we think a certain way rather than entertain preaching about how to fix it. Get to the core, you know? Daniel Pink seems to straddle that line, veering more into inspirational content than genuine research, so I'm not sure what to think about him despite generally liking the topics he discusses.

Had I not found the topic of regret intriguing, I likely wouldn’t have picked up a book of his by sheer force of his name. But, as it happens, my interests within psychology center around memory, storytelling, and other aspects that contribute to the reasons we regret (or don’t regret) our actions. On a personal level, I’m extremely aware of the concept of regrets at any given time because regretting my life is a deep and visceral fear of mine.

I’m glad I got to this one as a new release. My mind’s been elsewhere lately, but The Power of Regret was a pleasant and engrossing poolside read that took me approximately two hours this afternoon.

I underlined a ton. I enjoyed the entire thing. While I still find Daniel Pink to be a little light on the science and a little heavy on the anecdotes (which are relevant too!), his insights were overall tangible and clear. I appreciated how straightforward the book was about a topic that’s emotional, nuanced, and occasionally mind-boggling. How do we best structure our lives so as to avoid regret? (He counters the point that we shouldn’t always — X decisions are best to frame in this way, and Y are not.)

The Structure & Topic

The introduction talks about regret in general. What it means, how it trends, and the way we discuss it as a society. He uses the oft-cited No Ragrets tattoo from We Are The Millers, which is an accessible jumping point for many readers, because he begins the book in a series of interviews with people who have literally gotten “no regrets” tattooed on their body. He argues that their insistence of having “none” and the examples they use to back up that claim — everything led me to this moment — actually does point to the existence of regret, although they’re not inherently bad. Regret can be productive in that it teaches us how best to handle our next challenges or pivotal moments, and studies show that acknowledging that we wish we’d acted differently does motivate us to do better the next time around, contributing to our overall growth.

He then launches into a description of several baseline types of regrets, and the flavor of each: foundational regrets (that shape your life, like education, investing, and good habits), boldness regrets (“I wish I’d been brave enough…”), moral regrets, and connectional regrets.

Four Types of Regret

According to Pink, there are four main types of regret.

On a personal level, I tend to be afraid of having foundational regrets and get into an I have to do everything while I’m young mentality. As a note though, foundational regrets — mostly relating to stability over time — have a lot to do with privilege rather than intrinsic motivation. The border between what’s in your control and what’s due to external factors can get murky.

In general, I don’t get boldness regrets because I’m pretty bold about the shape of my own life and tend to do my own thing regardless of how it fits into conventions; I feel relatively good at being uncomfortable, which allows me to take advantage of cool opportunities. I grappled with moral regret a lot in my judiciary position on my university’s honor council, because it’s so integral to the way we conduct ourselves and our systems. In what ways does regret alleviate the pain of doing the wrong thing? On a philosophical plane, moral regrets are perhaps the most active in the way we conduct ourselves. For me, I’m not sure how often I do the right thing because of some innate spirit of goodness versus knowing the immoral choice would literally haunt me forever. (I love the George Saunders quote that, “my biggest regrets are failures of kindness” and that’s a guiding force for me.)

Connectional regrets are emotionally tough. I have this fear when I move or travel that I’ll leave and suddenly someone will die, and I’ll regret having been selfish by being far away. It hasn’t kept me from doing it (yet) but it’s perhaps the only force that could keep me rooted at home for long stretches of time.

Learning how each of these types of regrets shaped our personhood was illuminating, and being able to distinguish between proper ways of handling each was a great, bolstering framework.

Writing & Style

As I’ve mentioned, I find Daniel H. Pink sometimes relies too much on his own opinion and ability to synthesize. I sort of trust him as a loose thinker but I wish he cited more, brought up points that subverted and challenged his arguments, and overall incorporated more interdisciplinary thought. It feels like he’ll bring up a problem and a solution, but not fully address other factors that complicate his assertion. Perhaps I view it a little too academically, but I find that he’ll skip over some “what about…?”s in favor of sounding assertive about his conclusions. It makes me a little more skeptical of him as opposed to some other thinkers I follow. I'd read for some collected musings, but not give this book authority as a definitive source.

The writing itself is pretty simple and friendly. It feels like a good discussion you’re having with someone else rather than a professor. In that sense, his oversimplification makes him so overtly readable. The anecdotes could get a bit stale and similar after a while — we hear about a “no regrets” tattoo recipient in about every chapter, and I wish the situations had been a little more varied — but I had a grand time reading. I didn’t put it down, which is rare for a nonfiction, and The Power of Regret was quick enough for me to speed through during only one tanning session and its subsequent blackberry margarita.

Insights & Connections I Loved

• Most of what we regret involves situations we controlled. If something’s unfortunate but you have little agency over it, it’s tough to regret it because you can’t mentally time-travel and conceive of a way it would have unfolded differently.
• Regret is one of the most mentioned emotions — but also one of the most valued (because it does change you for the better, usually.)
• There are two types of reflections on regrets — If Onlys and At Leasts. At Leasts preserve our feelings in the moment but often lead to better performance later; If Onlys degrade our emotion in the present but can improve our lives (so it makes sense on an evolutionary level why we’re wired to feel regret.) Participants in a study who heard an If Only study literally scored 10 points higher on the LSAT than a control group who didn’t, and excelled in solving complex puzzles.
• What do people regret most? (I won’t spoil.)
• Regrets are closely tied to unconscious influences and cognitive distortions that bias our decision making. For more reading on that subject, I recommend The Art of Thinking Clearly by Rolf Dobelli for a quick and dirty overview.
• We tend to regret inaction more than action, not because inactions are worse, but because the way our brain processes them is different. When we act, we see the consequences unfold. When we don’t, we will always have an alternate universe of events in which we can speculate that things could have gone better. Due to that, inactions feel more vivid to us and we’re more often reminded of them, which means they could simply be more frequent regrets than more powerful ones.
• The book discusses our need for narrative, and how we view our lives in terms of stories. This topic deeply engages me, so I read often about it. Try this article or this read for more info.

Overall

The synopsis is accurate in that Daniel H. Pink is great at distilling complex topics into clear and accessible insights. The characterization that he draws from a wealth of neuroscience and biological research, on the other hand, feels a bit generous. I would have loved a bit more heft to his explanations at times so they didn’t feel overly simplified. Still, this is exactly the type of pop-sci read that’s perfect to sink into rather than study — a portal into a fundamental human feeling that shaped my thoughts on the subject.

Regret is something we all deal with and also try to avoid. That dynamic makes it a really interesting phenomenon to dive into, the flip side of nostalgia (which I adore studying.) Having the statistics of it laid out — at least with these survey results — allowed me to separate myself in an appealing and rewarding way, and I’m sure will influence my decision-making going forward. Love the topic, liked the writing, overall a win for me.

I bought this, and I’m glad I did, but I'd also be fine just checking it out once from the library or borrowing from a friend.

For fans of:

Atomic Habits by James Clear (lol); The Art of Thinking Clearly by Rolf Dobelli; anything by Neil deGrasse Tyson.