“I regret that I let a college counselor convince me that I didn’t have what it takes to be a doctor. I wish I had believed in myself and at least tried.”
Female, 54, Maryland
//
“I regret wasting so much free time before having children. In hindsight, I absolutely WAS NOT too busy to learn Spanish, exercise regularly, or put in extra effort at work to attain mastery.”
Male, 29, Indiana
//
“Not being more sexually active.”
Female, 71, Michigan
14.
Anticipating Regret
“Live as if you were living already for the second time and as if you had acted the first time as wrongly as you are about to act now!”
Viktor Frankl, 1946
One morning in 1888, Alfred Nobel awoke to a surprise in the morning newspaper. On the pages of the publication, in black and white for all to read, was his obituary. A French journalist had mistaken Alfred’s brother, Ludvig, who had died, for Alfred, who most assuredly had not. It was fake news for the fin de siècle set.
But what really rankled Alfred was how the obituary’s headline encapsulated his life’s work: “Le marchand de la mort est mort” （“The merchant of death is dead”）。
Nobel, a Swede who spoke five languages, was an ingenious chemist and an accomplished inventor. And what he invented were things that went boom: detonators, blasting caps, and, most famously, dynamite, which he patented in the 1860s. He built dynamite factories all over the world, which made him a multimillionaire and one of Europe’s most prominent industrialists.
Yet the obit didn’t tell a story of technical genius and entrepreneurial pluck. It described a contaminated soul with a shameful legacy—a greedy and amoral man who became fabulously wealthy by selling people tools for obliterating each other.
Eight years later, when Nobel did die, his will contained a surprise. Instead of leaving his fortune to his family, his estate established a set of prizes for “those who, during the preceding year, shall have conferred the greatest benefit on mankind”—the Nobel Prizes.
The impetus for this gesture, the legend goes, was that premature obituary.[1] Nobel glimpsed a preview of his future and he regretted what he saw. Anticipating this regret, he changed his behavior to avoid it.
If the previous two chapters were about regret through the rearview mirror, this chapter is about regret through the front windshield. Regret is a retrospective emotion. It springs into being when we look backward. But we can also use it prospectively and proactively—to gaze into the future, predict what we will regret, and then reorient our behavior based on our forecast. Sometimes that approach points us in a promising direction. Other times it can lead us astray. But if we understand both the upside and downside of anticipating regret, we can hone our strategy for pursuing the good life.
THE UPSIDE OF ANTICIPATION
Like most large research institutions, Duke University operates an extensive library system that serves its students, faculty, and staff. And like most organizations of any kind, Duke University Libraries wants to know what its customers and constituents think of its offerings. To assess opinion and gather feedback, DUL traditionally relied on surveys emailed to its community. But it faced a perennial problem: most people didn’t bother completing those questionnaires.
So, the crafty librarians of Duke hatched a plan—a simple experiment that sheds light on anticipated regret.
In 2016, DUL sent half of Duke’s six thousand undergraduates a survey and told them that if they completed and returned it, they’d be entered into a raffle for a $75 gift card.
The other three thousand students also received an email with the survey. But the accompanying rules were different. Everybody would be entered in a raffle for a $75 gift card. But if the organizers drew someone’s name and that person had not completed the survey, he would be ineligible for the prize and the organizers would select another name.
Which approach yielded the most survey responses?
It wasn’t even close. Within a week, only one-third of the students in the first group had completed the survey, but two-thirds of the students in the second group had done so.[2] The first instance was a good old-fashioned raffle. The second was what behavioral economists have come to call a “regret lottery.”
Regret lotteries are one way that anticipated regrets can alter our behavior. With an ordinary lottery, I must take affirmative steps to enter—in the Duke example, by filling out the questionnaire and returning it. If I don’t do that and someone who does ends up winning, I might be slightly bummed out （assuming I even find out）。 But with the odds slim and my emotional investment almost nonexistent, I’m unlikely to be devastated.