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Book Summary: The Power of Regret – How Looking Backward Moves Us Forward

The Power of Regret (2022) is a rebuttal of the “no regrets” worldview. Drawing from human psychology, it shares actionable steps for transforming emotion into action and using past disappointments to shape purposeful futures.

Who is it for?

  • Anyone who’s ever had a regret, no matter how big or small
  • Followers of the “no regrets” lifestyle who are ready to hear a new perspective
  • Psychology fans who want to explore the underpinnings of a popular phenomenon

Learn about and harness the power of regret.

“No regrets.” Chances are, you’ve heard this phrase more times than you can count. But what if I were to tell you that this approach to life – the no-regrets worldview – is totally wrong?

We shouldn’t stigmatize regret. We should embrace it. Regret has existed for as long as we have. It’s a completely normal emotion, and it deserves a place in everyone’s life. When done properly, looking backward can propel us forward – increasing our productivity, helping us find purpose, and leading us toward a more meaningful future. And there’s nothing regrettable about that.

Book Summary: The Power of Regret - How Looking Backward Moves Us Forward

In these summaries, you’ll learn

  • what famous historical figure used regret to turn his life around;
  • why Americans are more likely to feel regret than floss their teeth; and
  • how to successfully incorporate regret into your emotional portfolio.

Regret can change lives for the better – yours included.

On an April morning in 1888, Alfred Nobel woke up, opened the newspaper, and learned that he’d died. There it was in print – his obituary.

If that sounds confusing, just imagine how Alfred must have felt.

Of course, there’d been a mix-up. Turns out, Alfred’s older brother, Ludwig Nobel, was actually the one who had died – but the local press had mixed up the two siblings and published the wrong obituary. Because of this blunder, Alfred got the unique opportunity to see his legacy in print while he was still alive. And it wasn’t pretty.

“The Merchant of Death is dead,” blared the scathing headline. The obituary then proceeded to condemn Alfred for inventing dynamite and other explosives that are notorious for fueling worldwide destruction. It cast him as a money-hungry, immoral man who had accumulated a fortune at the expense of others – criticizing his greed and celebrating his (mistaken) death.

As you might imagine, Alfred didn’t like what he saw. All at once, he was overcome by a very human emotion: regret. But rather than casting this feeling aside, as many people do, Alfred confronted his regret head on and transformed it into something more meaningful. He used it as a catalyst for change – and his life was never the same from that moment forward.

Eight years later, when Alfred really did die, his legacy was completely different. People weren’t celebrating his death; they were celebrating his life. Rather than being remembered as a “merchant of death,” Alfred is now renowned as a philanthropist who bettered mankind.

If you’re not familiar with the story, here’s why. In Alfred’s will, he bequeathed 94 percent of his fortune to the creation of a now-famous series of prizes to be awarded to people who’d conferred the “greatest benefit on mankind” in physics, chemistry, physiology or medicine, literature, and peace.

Chances are, when you hear the word “Nobel,” you think “Nobel Prize” – not dynamite and death. And that’s exactly what Alfred wanted.

On that fateful April morning in 1888, when a newspaper published the wrong obituary, regret made a middle-aged man rethink the life he was leading and alter his trajectory in the time he had left. It was his catalyst for change – his impetus to move forward with greater purpose than ever before. And it can be yours, too.

As time-traveling storytellers, humans easily get swept away by regret.

Of course, Alfred Nobel isn’t the only man to have ever felt regret. Regret is one of the most common human emotions in the world, and almost everyone feels it at some point or another. In fact, a survey of 4,489 people across the United States found that Americans are more likely to feel regret than they are to floss their teeth. (Apologies to any dentists who are listening).

All in all, only one percent of survey respondents said they never look back on their life and wish they had done things differently. Meanwhile, a whopping 82 percent of people said that feeling regretful is at least an occasional part of their lives – and 43 percent of people said they engage in regretful thinking “frequently” or “all the time.”

That’s a whole lot of regret. But the statistics make sense, once you take a closer look at human nature. At their core, humans are – and this might be my new favorite definition of a human being – time-traveling storytellers. Our brains have the unique ability to revisit the past and invent alternative narratives – fictional storylines that never actually existed. This process is called counterfactual thinking. To see what it can look like in action, let’s take a trip to the 2016 Olympics in Rio De Janeiro.

The women’s road race had just ended . . . but only two of the three medal-winning cyclists were celebrating. While her competitors smiled and embraced loved ones, silver medalist Emma Johansson buried her head in her hands – then walked over to huddle quietly with her husband. Her facial expression was flat, far from celebratory.

She had just achieved an objectively incredible feat. But second place is a very tricky spot to be in, due to that pesky psychological phenomenon I mentioned earlier: counterfactual thinking.

To think counterfactually is to imagine how things could have gone – if only you’d done something else. The operative phrase here is “if only.” If only I’d gotten an extra five minutes of rest this morning. If only I’d eaten a bigger, or smaller, breakfast. If only I’d squeezed in 100 more hours of training, adjusted my breathing, or pushed a little harder, I would be wearing that gold medal.

Would Emma Johansson actually have won gold if any of those counterfactual scenarios were true? It’s impossible to say. And that’s exactly why the human brain obsesses over these types of questions. As a silver medalist at the Olympic Games, it’s all too easy to spiral into ruminative “if only” territory rather than celebrating your success.

Now, let’s return to Alfred Nobel for a moment. You see, Alfred was actually pretty anomalous in his reaction to regret. Upon reading the false obituary, he easily could have spiraled into regretful counterfactual thinking: If only I’d focused my life’s work on another invention, instead of dynamite. If only I had learned what people thought of me much earlier in my career. If only I could undo the destruction my creations have caused.

But punishing himself with this flurry of “if only”s would have been fruitless. So, instead, Alfred chose a much more productive route – taking action in the present to ensure he wouldn’t live with even more regret, tormented by still more “if only”s, in the years to come. While many people dwell in regret, Alfred used it to propel him toward a better future.

You see, there’s a big difference between unproductive regret and productive regret. While unproductive regret paralyzes, productive regret catalyzes. And which option you choose is entirely up to you.

Regret has a rightful place in our emotional portfolios.

We’ve already seen how regret paid off as a force of positive change in Alfred Nobel’s life. Now it’s time to share some unfortunate news: we’re living in a “no regrets” era, and society has emphatically swept this powerful emotion under the rug.

Around the world, the phrase “no regrets” is featured in song lyrics, tattooed on bodies, and cited in conversation time after time. Even the US Library of Congress contains more than 50 books with the title “No Regrets.”

But this popularly accepted “no regrets” worldview is completely wrong. Negative emotions like regret are essential to human growth – and denying them is downright dangerous. Think of your emotions as stocks. Would you invest in only one of two stocks, or spread your assets out across a portfolio?

As you may know, investing across a portfolio is the wiser option. We have a man named Harry Markowitz to thank for that knowledge. As an economics graduate student in the early 1950s, he came up with a now-famous idea known as “modern portfolio theory.”

The core principle of modern portfolio theory is this: don’t put all your eggs in one basket. Investing across a portfolio of stocks increases an investor’s chances of success, while investing in only one or two stocks limits their potential.

Well, it turns out this theory applies just as well to emotions as it does to the stock market. You see, our emotional portfolios contain many different stocks. Some are universally considered to be positive, like love, joy, and awe. Others are considered to be much more negative, like sadness, fear, or regret.

Without question, positive emotions should outnumber negative emotions in a healthy portfolio. But negative emotions do have their place in our list of investments, too. Fear shields us from threats, like burning buildings or dark alleyways. Disgust prevents us from consuming toxic substances. Then, of course, there’s regret, which can help us learn, grow, and achieve our full potential.

If you’re only investing in the positive stocks, it’s time to think twice. Learning to live with and learn from regrets is a stepping stone to a proactive, productive, and purposeful life. At the end of the day, “no regrets” simply means no growth – and that’s the most regretful choice of all.

So, how should we go about healthily investing in regret? Turns out, there’s a handy three-step process for doing exactly that. Let’s take a look.

Step one is to undo it. This applies to scenarios where you did something and then regretted it. Perhaps you said something mean-spirited to your significant other. Well, then it’s the perfect opportunity to “undo” your hurtful action with a sincere apology. Or maybe you estranged yourself from a friend years ago – well, it’s never too late to reconnect.

Of course, there are many scenarios where undoing simply isn’t possible. You may regret not learning a second language when you were in high school. And, true, you can’t turn back the clock and re-enroll in eleventh-grade Italian classes. But you can take action in the present. That’s where the other two steps of handling regret come into play.

Step two is to “at least” it. Maybe you regret attending medical school, but at least you wound up meeting your spouse there. That’s a big “at least”! Imagine a life without all the good things – wedding rings, babies in strollers, decades of love and companionship – that came from that one bad experience, medical school.

If there’d been no bad, you’d have missed out on all that good.

With that in mind, you might find yourself feeling grateful for those dreadful years of medical school since you now see them in a different light. And that’s exactly the point. Analyzing your regrets with a changed perspective can breed appreciation: giving objectively bad experiences a newfound purpose and making life more meaningful in the moment.

Finally, there’s step three: analyze and strategize. This is arguably the most important step of all, since it’s the one that promotes growth. During this step, you should ask yourself: What lessons can I learn from my regret?

In the next chapter, our final chapter, we’ll journey to Europe to see what this last step might look like in action.

Recognizing poor choices propels us toward more purposeful, productive futures.

It was 1988, and a 22-year-old American named Bruce sat on a train headed to Stockholm at the end of a year spent living abroad.

The train doors opened at a stop along the way, and on stepped a young Belgian woman named Sandra: an au pair working in Paris who was headed home for a short break. She sat next to Bruce, and the sparks began to fly.

Bruce and Sandra spent the next several hours talking, laughing, playing hangman, and solving crossword puzzles as though they’d known each other their whole lives. The chemistry was instant, intense, and unforgettable. But, as the train passed through Belgium, Sandra stood up and said, “I have to go.”

With that, Bruce was faced with a momentous decision: stay on the train and miss out on the potential love of his life, or get off and see where their relationship might go.

He wound up staying on the train. Bruce and Sandra kissed goodbye in a moment of passion, the train doors opened and closed, and just like that Sandra was out of Bruce’s life forever.

Bruce has regretted his decision ever since. Forty years later, he still says not getting off the train is the biggest regret of his life. “I never saw her again,” he wrote in the World Regret Survey, “and I’ve always wished I stepped off that train.”

Of course, not everyone will have an experience as momentous as Bruce’s. His Eurail experience is like something straight from a movie – a split-second decision that forever changed the course of his life. But no matter how big or small your regret is, there’s no upside of wallowing in it. Put yourself in Bruce’s shoes. After realizing he had made a big mistake, he could have beat himself up over it or started analyzing and strategizing.

Option one, beating himself up over the past, would only cause distress and disappointment. It’s a path that leads to nowhere. Analyzing and strategizing, on the other hand, is a much more productive path. While analyzing and strategizing, Bruce could have come up with the following action plan: Moving forward, I’m going to be bold and take risks. I’m going to follow my heart and tell people how I feel without hesitation. And if I ever find myself in another Eurail scenario – literally or metaphorically – I’m 100 percent going to step off that train.

To see successful strategizing in action, let’s look at Abby Henderson, a 29-year-old woman from Arizona who also participated in the World Regret Survey. Here’s Abby’s biggest regret: “I regret not taking advantage of spending time with my grandparents as a child. I resented their presence in my home and their desire to connect with me, and now I’d do anything to get that time back.”

Almost every winter, Abby’s grandparents would spend a month or two visiting from Indiana. When Abby returned from school, her grandmother would be waiting to hear how her day was – but Abby often shut down these conversations. Since she never made an effort to connect with her grandparents, she never got to hear their stories – and now that they’ve passed away, she never will.

But instead of beating herself up over the regret, Abby latched onto step three and started strategizing ways to mobilize her regret for better future outcomes.

Her grandparents are dead, so she can’t rewind time and collect their stories. But her father is alive and well, and she doesn’t want to make the same mistake twice – so she bought her father a subscription to StoryWorth. Every week, the service sends an email containing a single question – like “What’s your fondest childhood memory?” – and Abby’s dad responds with a story. When the year comes to a close, those stories are compiled into a hardcover book.

Abby is actively connecting with loved ones in the present so she doesn’t have regrets in the future. For her, regret revealed what is most precious in life – and prevented her from taking the same pathway twice.

We’ve walked through two examples of regret manifesting in people’s personal lives. But regret is a powerful force in professional lives, too – so let’s take a little foray into the business world.

In 2022, four social psychologists studied regret among negotiators who’d had their first offer accepted. Turns out, the more negotiators regretted their decision to not make a higher offer, the more time they spent preparing for subsequent negotiations. As a result, these individuals changed the way they operated in future negotiations – and wound up securing themselves a larger slice of the pie.

The bottom line? Recognizing poor choices is critical for growth. As the social psychologist Barry Schwartz explains, regret can “emphasize the mistakes we made in arriving at a decision” – this way, if a similar situation arises in the future, we won’t make the same blunders.

This was true for Alfred Nobel and Abby Henderson. And it can be true for you, too. So the next time you feel regret, pause and ask: What can I learn from this? Use regret as a catalyst for a life well led. Remember that regret in and of itself isn’t a bad thing – it has the potential to be a force of positive change. So reject the worldview that says regret has no place in our emotional portfolio.

Invest in regret, and you won’t regret it.

Final Summary

The key message in these summaries is that: Not only is the “no regrets” worldview wrong; it’s harmful to human growth. When approached properly, this powerful emotion can help you lead a more productive, purposeful life.

And here’s some more actionable advice: Pair New Years’ resolutions with “old year’s regrets.”

In late December, list your three biggest regrets from the past year – then make learning from and transforming those regrets your top New Years’ resolution. This way, your regrets will be reframed as catalysts for change in the coming months.

About the author

Daniel Pink is the acclaimed author of seven books, five of which earned spots on the New York Times bestseller list. His past titles include A Whole New Mind, Drive, Free Agent Nation, The Adventures of Johnny Bunko, To Sell Is Human, and When.

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