At the heart of all boldness regrets is the thwarted possibility of growth. The failure to become the person—happier, braver, more evolved—one could have been. The failure to accomplish a few important goals within the limited span of a single life.
The world of work, which most of us inhabit for more than half our waking hours, was especially fertile soil for these types of regrets. One thirty-three-year-old South African woman spoke for many when she wrote:
I regret not having the courage to be more bold earlier in my career and caring too much what other people thought of me.
Zach Hasselbarth, one of the people who regretted early shyness, recalls growing up in Albany, the capital of New York. “In Albany, you get a job. You go to work for New York State. You retire in twenty years. You have a pension, and then you die,” he told me. It was always easy to retreat into comfort, harder to pedal into uncertainty. Zach’s own father didn’t take many chances. But he told his son to abide what he said and not what he did. And what Zach’s father said was, “Don’t play it safe.”
Many of those who did play it safe in their careers look at their choices from the vantage of midlife and wish they hadn’t. A fifty-six-year-old man in Pennsylvania regrets “staying with my current company when I knew over fourteen years ago it would never satisfy,” just as a fifty-three-year-old man from Great Britain regrets “not leaving my safe job to follow my instinct and stay true to my core values sooner.” A fifty-four-year-old woman in Oregon regrets “not being bolder in my late thirties and taking a job in a new geographical area.” Then she collapses her regret to a single word: “Settling.”
One especially common boldness regret was not starting a business of one’s own. After years of working for a large pharmaceutical company, Nicole Serena did create a business, a consultancy and training company near Toronto. Her regret: not doing it sooner.
“I should have taken bolder actions earlier in my career,” said one California entrepreneur. “I got there eventually but wasted time listening to authority.”
A few respondents who launched businesses that closed down expressed regrets about excessive risk. They failed, they said, because they weren’t savvy or skilled enough or because they didn’t appreciate the demands of entrepreneurship. But these people represented a distinct minority compared with those who regretted never taking the leap. Many even hoped for a second try. For example, in 1997, the early days of the internet, Doug Launders started a web training company in central Florida. The venture “survived a few years and then failed,” he said.
I fell off the horse and decided that riding horses wasn’t for me. I spent the next twenty years handling the plow behind other people’s horses. I regret never getting back on the horse. At fifty-seven, I’m still trying to figure out how.
For some people, unrealized growth from their failure to take a risk was professional. But for many, it was personal. Many boldness regrets reflect a desire to grow not for any instrumental reasons but because of the inherent value of growth itself. For example, hundreds of people in the survey who turned down earlier opportunities to travel listed that decision as their top regret. If my regret-based dating app fails, I could instead launch an Expedia-for-the-regretful site, which would include special travel packages for the legions of college graduates in the surveys who regretted not studying abroad.
“It’s not the bad or stupid things I’ve done but the things I didn’t do that have caused me the most regret in life,” said Gemma West of Adelaide, Australia.
[My] biggest regret is not going backpacking around Europe when I was eighteen, because I was scared—an important rite of passage for Australians and something my best friend did with someone else.
A forty-seven-year-old woman from Utah said:
I regret not traveling more when I was younger—before I had a mortgage and child and “real job” and all the responsibilities of being an adult. Because now, I don’t feel like I have the freedom to do it.
Said a forty-eight-year-old Ohio man:
I regret not being more adventurous . . . taking time to travel, explore, and experience more of what the world has to offer. I let the fear of disappointment rule me and allowed others’ expectations to be more important than my own. I was always the “good soldier” and worked hard to please those around me. I have a good life—I just wish I had more experiences to share with others. Someday . . .
Boldness regrets, as with the Ohio man above, are often about exploration. And some of the most significant exploration, respondents said, is inward. Authenticity requires boldness. And when authenticity is thwarted, so is growth. The most telling demonstration of this point came from several dozen people from all over the world who described their regret—their failure to be bold—with the same five words: “Not being true to myself.”