The Power of Regret

Melancholy, 1891. Edvard Munch.

Claudia Cockerell May 23, 2024

In the winter of 1981, a 22-year-old Texan called Bruce was on a train through Europe. A girl boarded at Paris and sat down next to him. They started chatting, and it felt like they’d known each other their whole lives. After a while they were holding hands. When it came to her stop they parted ways with a kiss. They never traded numbers, and Bruce didn’t even know her surname. “I never saw her again, and I’ve always wished I stepped off that train,” he wrote, 40 years on, in his submission to The World Regret Survey. 

It’s a website you should visit if you ever need some perspective. Set up by author Daniel Pink, it asked thousands of people from hundreds of countries to anonymously share their biggest regrets in life. It’s strangely intimate, delving into the things people wish they’d done, or not done at all, and the answers run the gamut of the human condition. 

For all the people who regret cheating on their partners, there are just as many who wish they’d never married them in the first place. One 66-year-old man in Florida regrets “being too promiscuous,” while a 17-year-old in Massachusetts says “I wish I asked out the girls I was interested in.” The stories range from quotidian (“When I was 13 I quit the saxophone because I thought it was too uncool to keep playing”) to tragic (“Not taking my grandmother candy on her deathbed. She specifically requested it”). 

Sometimes we feel schadenfreude when reading about other people’s failings, but there’s something about regret that is pathos-filled and painfully relatable. Flicking through the answers, many of people’s biggest regrets are the things they didn’t do. We fantasise about what could have been if only we’d moved countries, switched jobs, taken more risks, or told someone we loved them.


“It just wasn’t meant to be. I still long for the sea - and to be near the waves”.


Pink wrote a book about his findings, called The Power of Regret. “We’re built 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”, he states. Why then, do we use our regrets to self-flagellate, more often wondering “if only…” rather than comforting ourselves with “at least”? 

“One of the biggest regrets I have is not moving to California after graduating college. Instead I stayed in the midwest, married a girl, and ended up getting divorced because it just wasn't meant to be. I still long for the sea - and to be near the waves,” writes one man in Nebraska. This pining reflects the rose tinted lens through which we look at what could have been. California with its rolling waves and sandy beaches is synonymous with a life of freedom, love, and joy.

Studland Beach, 1912. Vanessa Bell.

Instead of categorising regrets by whether they are work, money, or romance related, Pink has created a new system, arguing that regrets fall into four core categories: foundation, moral, boldness and connection regrets. Within these groups, there are regrets of the things we did do (often moral), and things we didn’t do (often connection and boldness regrets). The things we didn’t do are frequently more painful because, as Pink says, ‘inactions, by laying eggs under our skin, incubate endless speculation’. So you’re better off setting up that business, or asking that girl out, or stepping off the train, because of the inherently limited nature of contemplating action versus inaction. 

The actions which we do end up regretting are often moral failings that fall under the umbrella of a ten commandments breach. As well as adultery, larceny and the like, there’s poignant memories of childhood cruelty. A 56-year-old woman in Kansas still beats herself up about something she did 45 years earlier: “Throwing rocks at my former best friend in 6th grade as she walked home from school. I was walking behind her with my “new” friends. Terrible.” 

But regrets can have a galvanising effect, if we choose to let them. Instead of wallowing in the sadness of wishing we could rewind time, or take back something horrible we said or did, we can use that angsty feeling as an impetus for change. “When regret smothers, it can weigh us down. But when it pokes, it can lift us up,” says Pink. There’s an old proverb which has probably been cross-stitched earnestly onto many a cushion, but I still like it as a mantra for overcoming pangs of regret: “The best time to plant a tree is twenty years ago. The second-best time is today.”


Claudia Cockerell is a journalist and classicist.

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