I found myself in Hanover, New Hampshire last weekend —just across the river from Norwich, Vermont, where I was interviewing museum visitors for my ‘day job’—the one that pays the bills. Though I wasn’t thrilled at the idea of working over a holiday weekend, I consoled myself with the beauty of small-town New England in late spring. Besides, I could use a change of scenery, a respite from the hectic pace of my life in Boston and the stress of a recent visit to Cleveland, where I checked in on my elderly mother.

Hanover was just as I remembered it, bustling, picturesque, and prosperous, with stores selling everything from cookware to lingerie. It was if the town had just stepped out of a Gap ad—though ironically the Gap store on Hanover’s main drag had just closed, probably because the market had been saturated.

I felt a mix of comfort and discomfort, knowing that while I wasn’t brimming with youth like the Dartmouth students around me —I could easily pass among the townspeople with my H&M Polo shirt, my khaki pants, my topsiders and lightly tanned white skin.

I’ve often had the ability to blend in without trying, to fly below the radar. (On one visit to Jacksonville, Florida years ago, I picked up a white painter’s cap with the initials ‘WWJD’ above the brim. I grew attached to the $2 cap and assumed it was the moniker of a local radio station. It wasn’t until weeks later, when I was back in Boston, that a friend mentioned a movement among fundamentalist Christians and I discovered that I— a gay Jew—had been walking through the Bible-belt sporting a ‘What Would Jesus Do?’ hat).

As I checked out Dartmouth’s student center, I thought of my own college days at Northwestern University. Like many of these “kids,” I’d been privileged to attend an elite institution, if not quite Ivy League, than its Midwestern equivalent. But I never felt at home at Northwestern, even though on the surface I looked much like my classmates.

Inside, I was beset by doubts—about my sexuality and how I might come to accept it—about the anxiety and depression I carried like a yoke and tether, and a general sense of unworthiness that went along with the depression. I earned good grades and made friends while I felt like an imposter, just going through the motions.

Back in the student center, I walked by a cafeteria filled with students having lunch, talking, laughing.  I thought of the endless opportunities open to them, and how, as we age, choices lead to other choices, and that sense of possibility starts to evaporate like a summer shower. Looking at those young men and women with their bright eyes and unlined faces, I wondered what my own life would be like if I could go back to college, or return to my late twenties or early thirties today, if I could know then what I’ve figured out now.

Maybe instead of becoming a teacher of deaf children and choosing a “practical career” that didn’t pan out, I would have become an actor (my childhood dream), or a writer (in my youth, rather than waiting until my forties). I could have come out at 18 instead of 28, and saved myself hundreds, or possibly thousands of hours in therapy, trying to change my orientation during the intervening decade. But as I walked back toward my car, I realized that, while, “hindsight is 20/20,” the answers aren’t so simple.

I had to fumble and stumble, to pursue a series of false starts in my work and in my personal life, before the depression began to lift. I had to find my way, to develop a life that worked for me, regardless of how it looked to someone else. It has taken me all these years —into my mid-50s —to create that life, and I still haven’t put all the pieces together.

I haven’t found a meaningful relationship, and I’m still trying to reduce my anxiety and stress levels. But I am a writer, a teacher, and a storyteller. Today I don’t fly under the radar quite so easily, and I’m living a bit more ‘out loud.’

I drove south toward Boston, singing country songs along with Emmylou Harris’ Quarter Moon in a Ten-cent Town on my CD player. As I sang, I thought of opportunities lost, chances missed, and the chances that remain.

Maybe my second chance, rather than going back in time, is to use my heard-earned knowledge to enrich my life in middle age. “It’s gonna be easy from now on,” Emmylou sang, her voice conveying what I already know, that it won’t be easy at all.