While cleaning out my father’s apartment to get it ready for sale, my sister came across a stack of handwritten letters we had sent my grandparents in the early and mid-1980s. We had just left Florida for Connecticut, and letter writing was our primary means of staying connected. Long-distance calls were expensive, email wasn’t a thing yet, but a first-class postage stamp only cost twenty-two cents. My mother must have found these letters while sorting through my grandmother’s belongings after she passed and thought they were worth keeping. I’m glad she did.
In that stack was a letter I’d sent my grandmother when she was sick. I’d slipped a dollar inside—our grandmother always mailed us money, and I thought it would make her laugh. Apparently, it did. She kept the letter and the dollar tucked inside. I have it now. It’s still worth one dollar, of course, but its value to me is immeasurable.
There were notes from my sister too—one where she apologizes for talking back to my grandmother. I can only imagine how that went down. My grandmother was kind and generous, but she didn’t take any $hit from anyone.
But the letters that hit the hardest were the ones my brother Greg wrote when he was starting college. The move to Connecticut had been brutal on him—he’d just graduated high school in 1983 and was uprooted from the town and friends he’d known since he was little. My parents moved to Florida when he was three, so by the time he left he was, by all accounts, a Florida Man.
In one letter, he’s thrilled that our mother is making sausage and peppers for dinner. In another, he talks about applying for a short-order cook job at the golf-course snack bar down the street. I remember that job—Sterling Farms. I used to walk over there to hit golf balls and grab a burger from him. In yet another letter, he complains about the food at college (he was a foodie even then). He wasn’t wrong, by the way—I wound up attending the same school, and “Grade D But Edible” was printed right on the boxes.
But there was one letter that really got me. In it, he writes about our parents encouraging him to pursue a corporate path—the last thing he wanted. He shares how they made him feel like he wouldn’t get anywhere in life unless he followed that route. That hit me on two levels. First, I knew Greg loved the liquor business and dreamed of running his own shop. Being pushed toward a life you don’t want is disheartening, to put it mildly. Second, I had felt that same pressure. My dream had been to get a psychology degree, go on to graduate school, earn a Ph.D., and help people. But the closer I got to graduation, the more those conversations—mostly with my mother—shifted to, “So… what are you really going to do after college?” She nudged me toward working for a year first. I capitulated. The rest is history.
Greg did go into corporate life for a bit—Amex—but he didn’t love it. Then he got downsized. And when he finally followed his dream, with my father’s support, Glenville Wine and Spirits was born in 1993.
But this isn’t really about the careers we chose or the ones we didn’t. What it’s really about is this:
Letters last.
They outlive the moments we write them in.
They hold pieces of us that even we may forget.
And sometimes, decades later, they hand us back a part of someone we’ve lost.
Reading Greg’s letters didn’t just remind me of who he was—it helped me understand him more deeply than I ever did when we were kids living under the same roof. His words held fear, humor, frustration, hope… and his heart. Our hearts, really. These old letters built a bridge across forty years and brought me closer to my brother in a way I didn’t expect.
Greg is gone now, but his memory lives on. And perhaps his spirit does as well, in the words he left behind—proof that what we write matters, maybe more than we know.
