Author Jim Shepard Discusses Short Stories, Writing and Unhappiness

January 24, 2011

Jim Shepard and Carol Frost
Photo by David Noe

Author Jim Shepard and Director of Winter With the Writers Carol Frost

As an author whose work has been a finalist for the National Book Award and the recipient of a Pushcart Prize, Jim Shepard knows a thing or two about good writing—and comedic timing. On January 20, as the first author of the 2011 Winter With the Writers series, he read his short story, “Boys Town;” discussed the art of short stories, the madness of writers and the need for good readers; and punctuated all of it with his deft wit.

His short story, “Boys Town,” is about a 39-year-old former military man, who lives with his sardonic mother. He leads a life of false starts and directionless wandering, for which he expresses a precarious mix of both self-indictment and self-exoneration: “Here’s the story of my life: whatever I did wasn’t good enough, anything I figured out I figured out too late, and whenever I tried to help I made things worse. […] Whenever I was about to get somewhere, something would step in and block me. Whenever I was about to finally have something, something would happen to take it away.”

After the reading, Shepard sat down with Winter With the Writers Director Carol Frost to answer questions submitted by the audience.

While Shepard is the author of six novels, he joked that he enjoyed the challenge of short stories. He prefers the “guerrilla action of getting in, doing something and getting out again” to what he calls the “furniture moving involved in novels.” Though, he admits, their payouts leave a bit to be desired. “You know, the advantage of short fiction is so many fewer people read it. You reach fewer people. You get almost no money. Nobody has heard of you. You put less food on your children's table.”

It’s this need to create something meaningful even though few will read it and many will not appreciate it that drives writers—and leads to their misery. While writers are given the freedom to do whatever they want, they rarely feel good about themselves or their work and “the profession is run on, and is all about, rejection.” Given this, he advises young writers to “become friends with unhappiness.”

Most writers will not succeed. Some will attend MFA programs to improve their craft, but he maintains that most people don’t attend them thinking it’s a guaranteed golden ticket to a writing career. While he feels that there are too many writing programs, their proliferation doesn’t keep him up at night. “In fact, I kind of like MFA programs because if they're working right, they're teaching people how to be better readers,” he said. “And, God, we can use better readers out there.”

2011 Winter With the Writers

Events include master classes at 4 p.m. and readings, on-stage interviews and book signings at 7:30 p.m. Both are free and open to the public. Master classes and author readings and interviews will be held in the Bush Auditorium. Guests are encouraged to arrive early for the readings, as seating is limited. For more information, visit the Winter With the Writers website at or call 407-646-2666.

By Laura J. Cole

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