My line to writing was not a straight one

By Lisa Cupolo, winner of the 2020 W.S. Porter Prize for Short Story Collections

I was not a voracious reader from childhood, nor did I come from a bookish or scholarly family. I wandered in creative circles and it took ages for me to uncork my truth, that I wanted to write.  Winning the prestigious 2020 W.S. Porter Prize for short story collections was nothing short of thrilling, and a happy confirmation that I had finally arrived at the right place.

As it turned out, my gateway to writing began when I was thirty-one, and working as a server at the River Café in Calgary. I love to tell this story as a tale of assurance, that your destiny will indeed find you.  I was figuring out my next move, having returned from a year volunteering at an orphanage in Kisumu, near the border of Uganda. My friends were all established in their lives, buying houses and getting married and I was waiting tables and writing scripts with my roommate. I desperately wanted to get into publishing but felt that the bloom was definitely off my rose and that I was too old to start from scratch.

One night, I had a large table of middle-aged businessmen speaking Latin languages, the kind of men who snapped their fingers at me and ordered things like Kir Royale and Negronis. Luckily, I speak French and could just about handle their rudeness. But I noticed that one man stood out, he was kindly and younger than the rest, and he was buying $600 bottles of wine for the table. It became clear that this smiling man was in charge. He was the big cheese.

When I decanted another bottle of our cellar’s finest red, the kindly man touched my arm while I poured. “Listen,” he said, in his perfect Parisian accent, “I’m just a small town Canadian boy.” He looked me in the eye; he was flirting.

“I’m from Niagara Falls,” he said.

“Quoi?” I shrieked. “Qui êtes-vous?”  I couldn’t believe it. Call it divine timing, but I also come from that strange and wonderful tourist town. I recognized his surname; his mother had been an alderman when I was a kid.

When I told him my name, he jumped out of his seat. “Is your father Jerry Cupolo?”  Yes, I said. My parents owned the mom-and-pop sporting goods store in our small city. “I idolized your dad,” he said, “Your father gave me my first break. He loaned me a bike to start my own business.”

For the next hour, the two of us sat at a tiny table, captivated by the coincidence, and how many people we knew in common, much to the dismay of his snooty colleagues and the floor manager of the restaurant, who was steaming. At the end of the night the gentle hometown boy left me a $900 tip.  Yowza. That was very near the amount of money for a six-week publishing course in Vancouver that I thought I couldn’t afford. I quit that night, and signed up for the course.  Probably I would have been fired anyway.

Sometimes it’s hard not to believe that the universe is conspiring in your favor, as Paulo Coelho, famously said. One thing leads to another.  I was offered an entry level job at HarperCollins from a teacher at the course, and in March I drove across freezing cold Canada to take an entry level job at one of the big five publishers in Toronto.

In the past, I had worked as an editor in corporate photography and I’d just returned from that year in Kenya so I was hardly a wallflower when I started at HarperCollins. And yet.  I gophered for the vice president, who sent me home with stacks of books on weekends assuring me of a quiz on Monday morning.  He also sent me to Starbucks and to get his wife a Christmas present, and he pawned me off to the president to fetch his A&W root beer and burger every Friday lunch. 

My big secret, of course, was that once I got into publishing I had to acknowledge that I’d been writing for years. Why else put in the exhausting hours and take on the patriarchal bullshit. First, I loved being around books and writers, and second, I needed a job to survive.  I would begin writing at 5am every morning and then catch the subway downtown for work by 8. I barely covered my rent and subway fare with my take home wage and I was expected to eat and sleep publishing, which I did. It was an exhilarating time and I ended up working as a publicist with many of my favorite writers, Elmore Leonard, Neil Gaiman, Helen Humphries, Ann Patchett and many more.

Still, when my students ask me if going into publishing is a good transition to being a writer, I say no, absolutely not. I’ll never speak to you again if you do it.

But then, I smile.

With an MFA in fiction from the University of Memphis, Lisa’s stories have been published in Ploughshares, the Virginia Quarterly Review, Narrative, The Idaho Review, and others. She has been nominated for a Pushcart Prize and was a Tennessee Williams Scholar at the Sewanee Writers Conference.  She now lives in Southern California and is at work on a memoir. She teaches creative writing at Chapman University.