The Power of Regret: How Looking Backward Moves Us Forward

And what greater commitment to a belief system than to wear it literally on your sleeve—like Bruno Santos, who had the ethic enshrined in black lowercase letters between the elbow and wrist of his right arm?

If thousands of ink-stained body parts don’t convince you, listen instead to two giants of American culture who shared neither gender, religion, nor politics but who aligned on this article of faith. Leave “no room for regrets,” counseled positive thinking pioneer the Rev. Dr. Norman Vincent Peale, who shaped twentieth-century Christianity and mentored Richard Nixon and Donald Trump. “Waste no time on . . . regret,” advised Justice Ruth Bader Ginsburg, the second woman to serve on the U.S. Supreme Court, who practiced Judaism and achieved late-in-life goddess status among American liberals.[3]

Or take the word of celebrities if that’s your jam. “I don’t believe in regrets,” says Angelina Jolie. “I don’t believe in regrets,” says Bob Dylan. “I don’t believe in regrets,” says John Travolta. And transgender star Laverne Cox. And fire-coal-walking motivation maestro Tony Robbins. And headbanging Guns N’ Roses guitarist Slash.[4] And, I’d bet, roughly half the volumes in the self-help section of your local bookstore. The U.S. Library of Congress contains more than fifty books in its collection with the title No Regrets.[5]

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. Why invite pain when we can avoid it? Why summon rain clouds when we can bathe in the sunny rays of positivity? Why rue what we did yesterday when we can dream of the limitless possibilities of tomorrow?

This worldview makes intuitive sense. It seems right. It feels convincing. But it has one not insignificant flaw.

It is dead wrong.

What the anti-regret brigades are proposing is not a blueprint for a life well lived. 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.

And that is not some gauzy daydream, a gooey aspiration confected to make us feel warm and cared for in a cold and callous world. That is what scientists have concluded in research that began more than a half century ago.

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.



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We shouldn’t doubt the sincerity of people who say they have no regrets. Instead, we should think of them as actors playing a role—and playing it so often and so deeply that they begin to believe the role is real. Such psychological self-trickery is common. Sometimes it can even be healthy. But more often the performance prevents people from doing the difficult work that produces genuine contentment.

Consider Piaf, the consummate performer. She claimed—indeed, proclaimed—that she had no regrets. But a quick review of her forty-seven years on earth reveals a life awash in tragedy and troubles. She bore a child at age seventeen, whom she abandoned to the care of others and who died before turning three. Did she not feel a twinge of regret about that death? She spent one portion of her adult life addicted to alcohol and another addicted to morphine. Did she not regret the dependencies that stifled her talents? She maintained, to put it mildly, a turbulent private life, including a disastrous marriage, a dead lover, and a second husband she saddled with debt. Did she not regret at least some of her romantic choices? It’s difficult to picture Piaf on her deathbed celebrating her decisions, especially when many of those decisions sent her to that deathbed decades before her time.

Or take our far-flung tattooed tribe. Talk with them just a little and it’s clear that the outer expression of “No regrets”—the performance—and the inner experience diverge. For example, Mirella Battista devoted many years to a serious relationship. When it collapsed, she felt awful. And if she had a chance for a do-over, she likely would have made different choices. That’s regret. But she also acknowledged her suboptimal choices and learned from them. “Every single decision brought me to where I am right now and made me who I am,” she told me. That’s the upside of regret. It’s not as if Battista erased regret from her life. (After all, the word is permanently marked on her body.) Nor did she necessarily minimize it. Instead, she optimized it.

Amber Chase, who was thirty-five when we talked over Zoom one evening, told me, “There’s so many wrong turns you can take in life.” One of hers was her first marriage. At age twenty-five, she married a man who, it turned out, “had a lot of issues.” The union was often unhappy, occasionally tumultuous. One day, with zero notice, her husband disappeared. “He got on a plane and left . . . and I didn’t know where he was for two weeks.” When he finally called, he told her, “I don’t love you anymore. I’m not coming home.” In a blink, the marriage was over. If she had to do it over again, would Chase have married the guy? No way. But that unfortunate move propelled her journey to the happy marriage she has today.

Chase’s tattoo even winks at the flimsiness of the philosophy it claims to endorse. Hers doesn’t say “No Regrets.” It says “No Ragrets”—with the second word intentionally misspelled. The choice was an homage to the movie We’re the Millers, an otherwise forgettable 2013 comedy in which Jason Sudeikis plays David Clark, a small-time marijuana dealer forced to assemble a fake family (a wife and two teenage kids) to work off a debt to a big-time dealer. In one scene, David meets Scottie P., a sketchy young fellow who’s arrived on a motorcycle to take David’s “daughter” on a date.

Scottie P. wears a cruddy white tank top that reveals several tattoos, including one that runs along his collarbone and reads, in blocky letters, No Ragrets. David sits him down for a quick talk, which begins with a tour of Scottie P.’s tattoos and leads to this exchange:

    DAVID



(pointing to the “No Ragrets” tattoo)

    What is the one right there?

SCOTTIE P.

Oh, this? That’s my credo. No regrets.

DAVID



(his expression skeptical)

    How about that. You have no regrets?

SCOTTIE P.

Nope . . .

DAVID

Like . . . not even a single letter?

SCOTTIE P.

No, I can’t think of one.

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