The Power of Regret by Daniel H. Pink

I finished this book in August 2025. I recommend this book 7/10.

Why you should read this book:

This is the book that will provide you with tools to not just put your head down, but learning from your regrets to propel you forward.

Get your copy here.

🚀 The book in three sentences

1. "At least" is the silver lining.

2. What would you recommend or say to a friend?

3. Detach, and ask how your future self will feel.

📝 My notes and thoughts

• P37. At Least 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." I didn't get that promotion, but at least I wasn't fired." At least deliver comfort and consolation. If Onlys, by contrast, make us feel worse. "If only I'd begun that final chase two seconds earlier, I'd have won a gold medal." "If only I'd taken a few more stretch assignments, I'd have gotten that promotion." If Onlys deliver discomfort and distress. It would seem, therefore, that we humans would favor the first category—that we'd choose the warmth of At Least over the chill If Only. After all, we're bound to seek pleasure and to avoid pain—to prefer chocolate cupcakes to caterpillar smoothies and sex with our partner to an audit with the tax man.

• P54. Your response determines your result. When you feel the spear of regret, you have three possible responses. You can conclude that feeling is for ignoring—and bury or minimize it. That leads to delusion. You can conclude that feeling is for feeling—and wallow in it. That leads to despair. Or you can conclude that feeling is for thinking—and address it. What does this regret tell you? What instructions does it offer for making better decisions? For improving your performance? For deepening your sense of meaning? When feeling is for thinking, and thinking is for doing, regret is for making us better.

• P135. A fifty-one-year-old California man became disconnected from his father at age seven, when his parent got divorced. He visited his father every other weekend, but "the relationship was shallow... no deep conversations, nor getting to really know each other." By the middle school, the visits stopped. The man reconnected somewhat with his father in his late teens and early twenties, but: Still, during all that time we didn't get to build any sort of bond...He passed away seventeen years ago, and I often regret not having a beer with him as an adult man."

• P141. How would she feel if Jen reached out to her? "If I got a message from her today, oh my God, I would burst into tears," she told me. "That would be a life-changing thing for me to hear from her and for her to still be thinking about our friendship after all those years."

• P165. At Least can turn regret into relief. On their own, they don't change our behavior, but they change how we feel about our behavior, which can be valuable. And because At Least springs to mind naturally for less often than If Onlys, we must summon them ourselves at the right time. At Leasts work like antibiotics. Sometimes we need to reach into the medicine cabinet and pop a few of them to fortify our psychological immune system and fight off certain harmful emotions. If we use these antibiotics too often, their efficacy will wane. If we use them intelligently, they can aid in healthy functioning. So, with action regrets that are bringing you down, ask yourself:

  • How could the decision I now regret have turned out worse?

  • What is one liver lining in this regret?

  • How would I complete the following sentence? "At least..."

• P172. Self-disclosure is intrinsically rewarding and extrinsically valuable. It can lighten our burden, make abstract negative emotions more concrete, and build affiliation. So, to begin to harness your regret to improve in the future, try any of the following:

  • Write about your regret for fifteen minutes for three consecutive days.

  • Talk about your regret into a voice recorder for fifteen minutes for three consecutive days.

  • Tell someone else about the regret in person or by phone. Include sufficient detail about what happened, but establish a time limit (perhaps a half hour) to avoid the possibilities of repetition and brooding.

• P176. So, drawing on the science of self-compassion, the second step in transforming our regrets is to ask ourselves three questions:

  • If a friend or relative came to you with the same regret as yours, would you treat that person with kindness or contempt? If your answer is kindness, use that approach on yourself. If your answer is contempt, try a different answer.

  • Is this type of regret something that other people might have endured, or are you the only person ever to have experienced it? If you believe your stumble is part of our common humanity, reflect on that belief, as it's almost always true. If you believe the world has it out for you alone, please reread Chapters 7-10.

  • Does this regret represent an unpleasant moment in your life, or does it define your life? Again, if you believe it's worth being aware of the regret but not over-identifying with it, you're on your way. If you believe this regret fully constitutes who you are, ask someone else what they think.

• P181. So, to gain the benefits of self-distancing, try any of the following:

  • 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? Be as specific as you can. Now follow your own advice.

  • Imagine that you are a neutral expert—a doctor of regret sciences—analyzing your regret in a clean, pristine examination room. What is your diagnosis? Explain in clinical terms what went wrong. Next, what is your prescription? Now write an email to yourself—using your first name and the pronouns "you"—outlining the small steps you need to learn from the regret.

  • If your regret involves your business or career, try a technique from the late Intel CEO Andy Grove, who reportedly would ask himself, "If I were replaced tomorrow, what would my successor do?"

  • Imagine it is ten years from now, and you're looking back with pride on how you responded to this regret. What did you do?

• P183. Seven Other Techniques You Won't Regret.

• P203. Call it the Regret Optimization Framework. This revised framework is built on four principles:

  • In many circumstances, anticipating our regrets can lead to healthier behavior, smarter professional choices, and greater happiness.

  • Yet when we anticipate our regrets, we frequently overestimate them, buying emotion insurance we don't need and thereby distorting our decisions.

  • And if we go too far—if we maximize on regret minimization—we can make our situation even worse.

  • At the same time, people around the world consistently express the same four core regrets. These regrets endure. They reveal fundamental human needs. And together, they offer a path to the good life.

• P204. If the decision does involve one of the big four, spend more time deliberating. Project yourself into the future—five years, ten years, at age eighty, whatever makes sense. From that future vantage point, ask yourself which choice will help you build your foundation, take a sensible risk, do the right thing, or maintain a meaningful connection. Anticipate these regrets. Then choose the option that most reduces them. Use the framework a few times, and you will begin to see its power.

• P205. What To Do With Your Regrets: A Recap.