In the fall of 1946, my grandfather was twenty years old and back home in Pittsburgh, having completed his English degree at Purdue and a tour with the navy. Though he was expected to join the family diamond business, Richard Max Davis dreamed of becoming a writer—he just wasn’t sure how to do it. So he wrote a letter to Malcolm Cowley. And Malcolm Cowley wrote back.

There was a family connection: Cowley was my great-grandfather’s Harvard roommate and a fellow Pittsburgh native. Cowley’s enduring fascination with the personalities and destinies of American writers is evident, as is—I imagine—a note of paternal affection.

In the weeks since I discovered Cowley’s 1947 letter among some family papers, I have often paused to consider his message: writing is difficult; most writers are failures. If you have to ask if you should become a writer, you are probably not a writer. A postgraduate writing course? Can’t hurt, but that’s almost beside the point.

The letter makes me smile as I imagine my grandfather, sepia and stern-faced, among his twenty-first-century peers in an Iowa workshop. He fretted over a course in fiction writing decades before it was common for aspiring writers to ask such a question—and Cowley answers him.

But it also pains me, in no small part because the correspondence is one–sided. What did my grandfather write to Cowley? I can feel Richard Max’s anxiety as he typed his letter, and I can feel his heart sink as he read Cowley’s words. Certainly, it will delight Louis Menand fans and cultish observers of the Harvard curriculum (they exist) to learn that the self-appointed curator of the Lost Generation wished he’d taken more science courses. But what did it mean to an ambitious twenty-year-old man, fresh from a minesweeper, eager to avoid the family business?

My grandfather did not “become” a writer. (As Cowley might say, does one ever?) He joined the diamond business and soon had a wife and three young children. At least one Hemingway dream remained: he was an avid deep-sea fisherman. In January 1964, while on a fishing vacation in the Cayman Islands, Richard Max Davis set out toward Cuban waters in a twelve-foot outboard motorboat and was never seen again. —Rebecca Davis O’Brien