The Power of Regret: How Looking Backward Moves Us Forward



To identify a foundation regret in yourself or in others, listen for the words “too much”—whether they attach to consuming alcohol, playing video games, watching television, spending money, or any other activity whose immediate lure exceeds its lasting value. Then listen for the words “too little”—whether they describe studying in school, setting aside cash, practicing a sport or musical instrument, or any other undertaking that requires steady commitment. One study of college athletes, for example, found that their greatest regrets centered on too much eating and too little sleep and training.[2]

Temporal discounting is only the beginning, because this deep structure category involves a second time-based issue. Some regrets deliver their pain immediately. If I race my car down the street well above the speed limit and collide with another vehicle, the consequences of the decision, and therefore my regret, are instantaneous. A totaled vehicle, an aching back, a lost day. But foundation regrets don’t arrive with the sound and fury of a collision. They proceed at a different pace.

In chapter 13 of Ernest Hemingway’s 1926 novel The Sun Also Rises, a few of protagonist Jake Barnes’s expatriate friends arrive in Pamplona, Spain, and meet for a drink. During the conversation, Mike Campbell, a Scotsman, discloses his recent bankruptcy.

“How did you go bankrupt?” American Bill Gorton asks him.

“Two ways,” Campbell replies. “Gradually and then suddenly.”[3]

That’s also how people discover their foundation regrets. Many individual health, education, or financial missteps are not themselves immediately devastating. But the slowly building force of all those poor decisions can arrive like a tornado—gradually and then suddenly. By the time we realize what’s happening, there’s not much we can do.

Once again, people used similar language to describe regrets whose consequences they understood too late. A sixty-one-year-old Florida man, unintentionally channeling Hemingway’s laconic style, wrote:

    Not saving money from an earlier age. Compound interest.



A forty-six-year-old Australian said:

    I should have selected different subjects and worked harder earlier in my life to obtain the compounding benefits throughout life.



A thirty-three-year-old Michigan man:

    I regret that I didn’t appreciate reading earlier in life. Now I see the value of reading and often wonder what the compounding effect would have been if I had started ten to fifteen years earlier.



Compounding. It’s a powerful concept, but one our grasshopper minds struggle to comprehend.

Suppose I offered you a choice—$1 million in cash today or one penny that will double in value every day for a month. Most people, experimental evidence shows, would opt for the million bucks.[4] And during the first three and a half weeks of our pact, that decision would seem wise. But after just a little more time—on day thirty—that penny would become more than $5 million. We can explain the power of compounding with another chart, which you’ll notice is essentially the mirror image of its predecessor.





Compounding interest





If you invest $10,000 at a 5 percent compounding interest rate, you’ll have an extra $500 after one year. After ten years, you’ll have made nearly $6,500. After twenty years, you’ll almost triple your money. But after thirty years, your stake will be worth over $44,600—more than quadruple what you started with. In the short run, the interest on money you’ve borrowed or saved doesn’t add up to much. In the medium run, it accelerates. In the long run, it explodes. And the principle applies well beyond finance—because small choices about eating, exercising, studying, reading, and working produce explosive benefits or harms over time.

Our brains therefore play a double trick on us. They entice us into valuing the now too much and the later too little. Then they prevent us from understanding the nonlinear, compounding effects of our choice. Overlay the two charts, and they form a trap that can be difficult to escape.

Foundation regrets are not just difficult to avoid. They are also difficult to undo. That is especially the case for financial regrets like Jason’s, which people described in vivid terms. A fifty-five-year-old California woman said the debt she’s amassed from shortsighted money choices “entangles my feet.” For a forty-six-year-old Indian man, lacking a financial foundation prevented him from “having the space to live life.” “The money I could have saved makes me a bit sick to my stomach when I think about what I wasted,” said a forty-seven-year-old female from Washington State. And a forty-six-year-old woman from Massachusetts who didn’t learn “how to manage money better, sooner” concluded that “most of my other regrets all seem to lead back to that one.”

Foundation regrets were evenly spread across geography and gender. But they were slightly more prevalent among older respondents, because weaknesses in one’s foundation take time to develop and recognize. Said a Tennessee man:

    I should have worked harder in college. Achieving better grades would have allowed me to get a better job, earning more, sooner in my career.



At age nineteen, this man’s foundation seemed sound. At age twenty-nine, it creaked. At age thirty-nine, it wobbled. Now, at age forty-nine, it feels like it’s disintegrating. His footing is shaky because of a set of seemingly small decisions he made three long decades ago. But even younger people, who hadn’t yet witnessed the results of their mistakes compound, shared this category of regrets. “I wish I would have studied harder,” said a twenty-five-year-old Malaysian woman. “I wish I had worked harder in college and spent my time more judiciously,” said another twenty-five-year-old woman, who lives in India.

Many respondents lamented not only the practical ramifications of not tending to one’s foundation, but also a more wistful sense of lost opportunity. A forty-nine-year-old woman, more than two decades removed from college, wrote:

    I wish I had appreciated the privilege I had to be able to go to university and had worked harder to get a better degree.



The pattern is similar for health decisions—including poor eating habits and lack of exercise—which also gather force and imperil people’s foundations. In the World Regret Survey, regrets about tobacco use, particularly starting at a young age, came from respondents on six continents—including this thirty-nine-year-old man from Colombia:

    I regret I smoked so much in my life, even though I clearly knew how bad for my health and surroundings this was. I kept smoking a pack a day, sometimes more. I escaped my frustrations and anxiety by smoking cigarettes.



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