The pain of boldness regrets is the pain of “What if?” Thomas Gilovich, Victoria Medvec, and other researchers have repeatedly found that people regret inactions more than actions—especially in the long term. “Regrettable failures to act . . . have a longer half-life than regrettable actions,” Gilovich and Medvec wrote in one of their early studies.[3] In my own American Regret Project survey, inaction regrets outnumbered action regrets by nearly two to one. And other research has likewise found a preponderance of inaction regrets even in less individualistic cultures, like those of China,
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