Before I was a columnist in Northern Colorado, I wrote for another publication where I was sometimes tasked with interviewing community members about their vocations and avocations. Given the intended low-key nature of these pieces (i.e., fluff in journalistic parlance), I’d been coached by my editor to not appear skeptical or interrogating, but to merely take the interview subject’s word for… whatever. In other words, listen, smile, write it down, and make the subject look good.
One of these interviews was with an entrepreneur about his latest venture. Near the end of the interview, I asked him if he had any regrets or wished he’d done anything differently with his undertaking. His response was that everything turned out perfectly. He then doubled down by saying that he had no regrets about anything he’d ever done. I kept a straight face (so I could keep my job), but his answer surprised me nevertheless and told me more about him than any of his previous responses. I mean, who doesn’t have regrets or is so arrogant or insecure not to acknowledge them?
Remembering that interview got me thinking about some of my own regrets:…