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.
“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.