“Oh, God,” she replied. “My father would kill me!”
They walked through the train aisle to the door. They kissed. Bruce madly scribbled his name and his parents’ Texas address on a slip of paper and handed it to her. The train doors parted. She stepped off. The doors closed.
“And I just stood there stunned,” said Bruce, who is now in his sixties and who asked that I not use his last name.
When he returned to his seat, his fellow passengers asked why he hadn’t left the train with his girlfriend.
“We just met!” Bruce told them. He didn’t even know her name. They hadn’t exchanged names, Bruce explained, because “it was almost as if we already knew.”
The following day, having made it to Stockholm, Bruce boarded a flight back to the United States.
Forty years later, when he completed the World Regret Survey, he relayed this tale and concluded, “I never saw her again, and I’ve always wished I stepped off that train.”
* * *
—
If foundation regrets arise from the failure to plan ahead, work hard, follow through, and build a stable platform for life, boldness regrets are their counterpart. They arise from the failure to take full advantage of that platform—to use it as a springboard into a richer life. Sometimes boldness regrets emerge from an accumulation of decisions and indecisions; other times they erupt from a single moment. But whatever their origin, the question they present us is always the same: Play it safe or take a chance?
With boldness regrets, we choose to play it safe. That may relieve us at first. The change we’re contemplating may sound too big, too disruptive, too challenging—too hard. But eventually the choice distresses us with a counterfactual in which we were more daring and, consequently, more fulfilled.
Boldness regrets sound like this: If only I’d taken that risk.
SPEAKING UP AND SPEAKING OUT
Regrets of boldness often begin with a voice that isn’t heard. Zach Hasselbarth, a thirty-two-year-old consumer lending manager in Connecticut, offered this to the World Regret Survey:
I let the fear of what others would say stop me from being more outgoing in high school. I regret not taking more chances and being so shy.
“Back then,” he told me in an interview, “I thought it was the end of the world if I got rejected; I thought it was the end of the world if they said no.” So he lowered his head, never talked much, and rarely announced his presence. Later in life, thanks to a more fearless college roommate, Zach unlearned some of that behavior. But he still knocks himself for the opportunities he missed and the contributions he didn’t make.
Several survey respondents used language almost identical to that of a thirty-five-year-old British Columbia man whose regret was “not learning to speak up for myself . . . in love, in school, in my family, or in my career.” Some described “fearing my own voice.” An enormous number of people of all ages and nationalities regretted being “too introverted.”
Introversion and extroversion are fraught topics, in part because popular belief and legitimate science often depart. The conventional view, reinforced by the ubiquity of assessments like the Myers–Briggs Type Indicator, holds that we’re either introverted or extroverted. But personality psychologists—the scientists who began studying the subject a hundred years ago—have long concluded that most people are a bit of both. Introversion and extroversion are not binary personality types. This trait is better understood as a spectrum—one where about two-thirds of the population lands in the middle.[1] Yet almost nobody in either the quantitative or qualitative regret surveys described excesses of extroversion, while many lamented tilting toward the other side of the scale.
For example, a California man regretted using his “introvert tendency as an excuse” for “not speaking up” in the classroom, the office, and even “when competing athletically.”
A forty-eight-year-old woman in Virginia said:
I regret allowing my shyness [and] introversion . . . to keep me from moving to a larger market where job opportunities, activities, and dating pools are better than where I am living now.
A fifty-three-year-old man from the United Kingdom said:
I regret being too shy and polite as a teenager and young adult, always taking the safe path and not offending people. I could have taken more risks, been more assertive, and had more life experiences.
As a card-carrying ambivert who prefers the company of quiet people, I’ve cheered from the sidelines when others have decried the “extrovert ideal” in Western culture. Yet the evidence shows that modest efforts to move slightly in that direction can be helpful. For instance, Seth Margolis and Sonja Lyubomirsky of the University of California, Riverside, have found that asking people simply to act like an extrovert for one week appreciably increased their well-being.[2]
Similarly, many people who overcame their apprehensions and poured out even a small tincture of temerity reported being transformed—including this fifty-six-year-old North Carolina woman:
I did not learn to find my own voice until having children and being their voice. Before that, particularly in school, I never said anything in classes where there were bullies or mean kids. I did not know how to speak up then. I wish I would not have been so quiet.
STEPPING UP AND STEPPING OUT
A few months after his encounter on the Eurail train, Bruce was living in College Station, Texas, when his mother forwarded him a letter bearing a French stamp and Paris postmark that had arrived at her home. Inside was a sheet of paper filled top to bottom with billowing handwriting.
The letter’s English was imperfect, and perhaps consequently, its sentiment was slightly inscrutable. Bruce now knew the woman’s name—Sandra—but not much else. “Maybe it’s crazy, but when I think about you, I’m smiling,” Sandra wrote. “I’m sure you understand what I feel about although you don’t know me well.” The words sounded tender—except for the oddly perfunctory conclusion: “Have a great day!” Sandra didn’t sign her last name, nor did she include a return address.
In the pre-internet era of the early 1980s, that halted communication. For Bruce, the doors had opened—and closed—again.
Rather than try to track her down, he chose to throw away the letter.