Robert Gentil spent several decades in New York’s financial markets before retiring to Richmond, Virginia, where he now splits his time between his garden, his reading chair and the telescope on his third-floor balcony. In this Q&A, he talks about how his idea of success has changed over the years, and what it actually looks like to him now.
How Did You Define Success Early in Your Career?
Early on, I defined it the way most people in finance do: by results. Did the analysis hold up? Did the decision protect the client’s money? Did I stay calm when the market didn’t? I was proud of being someone people trusted during periods of uncertainty. That felt like success at the time, and honestly, it still does.
Was There a Specific Moment When You Felt You Had Made It?
Not one big moment. It was more a pattern I noticed over years. Colleagues would come to me before making a difficult call, not because I had a better forecast than anyone else, but because I wasn’t going to panic. That reputation took a long time to build. I think that’s closer to real success than any single trade or promotion.
How Has Your Definition of Success Changed Since You Retired?
It’s gotten smaller and more immediate, which I mean as a compliment to it. In New York, success was measured over quarters and years. Now it’s measured in a morning. Did I get through my reading? Did I get the garden weeded before it got too hot? Did I write down something worth remembering about the night sky? Those are small things, but they add up to a life I’m satisfied with, which is really what success was always supposed to feel like.
Does Your Financial Background Still Shape How You Think About It?
It shapes how I evaluate anything, honestly. In finance, you learn to separate what actually happened from what you wish had happened. I apply that to my own life now. If I ask myself whether a week went well, I try to be as honest about that answer as I’d want to be about a portfolio. It keeps me from fooling myself.
You Volunteer Some of Your Time With Students on Financial Literacy. What Does Success Look Like There?
I don’t measure that by whether they remember every term I use. I measure it by whether they leave the conversation asking better questions than they arrived with. If a young person walks away thinking more carefully about saving or debt or patience, that’s a success I’ll take over almost anything I accomplished professionally.
Has Living in Richmond Changed How You Think About Success?
It has, in a quieter way than I expected. New York measures success loudly. Richmond measures it in smaller gestures: a neighbor you helped move a bookshelf, a historic home you helped keep from falling apart, a conversation on a porch that ran longer than either person planned. None of that shows up on a résumé, but I’ve come to think it matters just as much.
What Would You Tell Someone Who Is Chasing Success the Way You Once Did?
I’d tell them to pay attention to what they’re actually chasing. For a long time, I assumed success meant being right more often than I was wrong. Later I realized it also meant being someone people could rely on when things weren’t going well. That second part took me longer to appreciate, and I wish I’d understood it sooner.
What Does a Successful Day Look Like for You Now?
A cup of coffee, the newspaper, an hour with a good book, some time in the garden, and if the sky is clear, an hour on the balcony with my telescope. If I’ve learned something I didn’t know that morning, and I haven’t rushed through any of it, I count that as a good day. That’s a much simpler standard than the one I used to hold myself to, but it’s a fair one.