The Power of Regret: How Looking Backward Moves Us Forward

On mental health, foundation regrets often involve a failure to recognize the problem and seek a remedy. As a forty-three-year-old Oregon man put it:

    I regret that I didn’t take my mental health seriously in my twenties and, in doing so, utterly lost my sense of self-worth.



Many people who did take steps to rebuild a collapsing psychological foundation regretted not beginning the process sooner. For example, a forty-four-year-old Arizona woman said:

    I regret not finding a good therapist ten or fifteen years earlier.



And a fifty-seven-year-old nonbinary person in Oregon regretted:

    Not taking antidepressants in 2002 when first prescribed, and waiting until 2010. They have been a godsend, and I regret that those eight years could have been so much different had I started earlier.



Embedded in each of these regrets is a solution. Just as foundation regrets can be defined with a well-worn fable, one response to them is contained in a hoary Chinese proverb:

The best time to plant a tree is twenty years ago.

The second-best time is today.





FOUNDATION ATTRIBUTION ERROR


Foundation regrets are trickier than the other three deep structure regrets I’ll describe in upcoming chapters. Remember that what distinguishes regret from disappointment is personal responsibility. Disappointments exist outside of your control. The child who wakes up to discover that the Tooth Fairy hasn’t left her a reward is disappointed. Regrets, in contrast, are your fault. The parents who awaken and realize they forgot to remove their child’s tooth and replace it with a reward are regretful. But when it comes to matters like physical health, educational attainment, and financial security, the border between personal responsibility and external circumstance is murky.

Are you overweight because of your poor nutritional choices or because nobody ever taught you, let alone modeled, healthy eating? Do you have a meager retirement account because you spent too much on frivolities or because you started your career burdened with student debt and lacking even a thin financial cushion? Did you drop out of college because of your faulty work ethic or because your mediocre secondary school didn’t prepare you for the rigors of university classes?

One of the most prevalent cognitive biases—in some ways the über-bias—is called the “fundamental attribution error.” When people, especially Westerners, try to explain someone’s behavior, we too often attribute the behavior to the person’s personality and disposition rather than to the person’s situation and context.[5] So, to use a classic example, when another driver cuts us off on the highway, we immediately assume the person is a jerk. We never consider that the person might be speeding to the hospital. Or when someone seems uneasy while giving a presentation, we assume that he’s an inherently nervous person rather than someone who doesn’t have much experience in front of a crowd. We load too much explanatory freight onto the person and too little onto the situation.

With this category of regrets, something similar might be happening—a foundation attribution error. We attribute these failures, in ourselves and others, to personal choices when they’re often at least partly the result of circumstances we can’t control.[*] That means that the fix for foundation regrets, and a way to avoid them, is not only to change the person, but to reconfigure that person’s situation, setting, and environment. We must create the conditions at every level—society, community, and family—to improve individuals’ foundational choices.

Which is what Jason Drent is trying to do.





LESSONS FROM A GRASSHOPPER


In his current job, Jason oversees workplace policies and programs for a retailer that employs more than a thousand associates, many of them young. He approaches the position with a greater sense of mission than he did back when he was a teenager peddling DVD players at Best Buy. “I help them navigate a lot of the basics in life. I’m not the only one with a less-than-great foundation,” he said.

He explains to the associates the importance of building their skills and connections and, yes, putting aside a little from every paycheck for the future. He tells them to plan, then tries to show them how—all while attempting to heed the advice himself.

“I’m very transparent about being forty-three and not having any money. I only wish more forty-three-year-olds had been honest with me [when I was younger],” he said. “I’m telling the cautionary tale of the grasshopper.”

All deep structure regrets reveal a need and yield a lesson. With foundation regrets, the human need it lays bare is stability: we all require a basic infrastructure of educational, financial, and physical well-being that reduces psychological uncertainty and frees time and mental energy to pursue opportunity and meaning.

The lesson reaches back two and a half millennia. Think ahead. Do the work. Start now. Help yourself and others to become the ant.

    “When I was 13 I quit the saxophone because I thought it was too uncool to keep playing. Ten years later I realize oh how wrong I was with that assessment.”

Male, 23, California

//


“Thinking that working eighteen hours a day, six days a week, when I first started out would help me become successful. Instead, I destroyed my marriage and almost my health.”

Male, 68, Virginia

//


“I regret not getting married in front of my mother. My husband-to-be was in the military and we had to get married fast and in Oklahoma, which is far from Ohio. She was very ill and died a month later. I could have given her the happiness of seeing me married and I selfishly didn’t work to make that happen.”

Female, 51, Ohio





8.


    Boldness Regrets



One November evening in 1981, a twenty-two-year-old American named Bruce was on a train speeding northward through France when a young woman boarded at a Paris station and took the seat next to him. Bruce’s French was meager. But the woman’s English was decent, and they began talking.

Bruce had spent the past year in Europe. He’d lived with a family in Sweden, worked odd jobs, and hitchhiked across the continent. Now he was heading to Stockholm to catch a flight back to the United States. He was in a hurry; his Eurail pass expired the next day.

The woman, a brunette perhaps a year or two younger than he, was from Belgium. She’d been working in Paris as an au pair, and was traveling back to her small Belgian hometown for a short break.

The conversation came easily. Soon the two were laughing. Then they were playing hangman and doing crossword puzzles. Before long, they were holding hands.

“It was truly as if we had known each other our whole lives,” Bruce told me recently. “And I have never felt that way again.”

The train chugged on. The hours raced by. Just before midnight, as the train was approaching a station in Belgium, the woman stood up and told him, “I have to go.”

“I’ll come with you!” Bruce said.

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