Award-winning author Garth Greenwell was the guest speaker at the annual Mountcastle Lecture on January 28, 2026, which was part of the Writers at Work series. After reading off a list of his numerous accomplishments, like being a Distinguished Writer in Residence at New York University, Tickner Writing Fellow Johannes Lichtman summarized, “He’s kind of a big deal.”

Greenwell announced to the audience of Upper School students and faculty that he would speak on the “relationship between art and life and what it means to dedicate your life to art, and the relationship between art and failure.” He shared that the reason he became a writer stems back to the ninth grade when he failed English class. 

The story began in Louisville, Kentucky, where Greenwell grew up, and took twists and turns along the way. Greenwell had been kicked out of his father’s house after learning Greenwell was gay, and although he had a supportive home at his mother’s, all his books and notes were at his dad’s. Doing poorly in English meant he needed extra credit, which led him to audition for the school choir. The choir teacher saw potential in him and offered him free voice lessons after school. “I wouldn’t understand how generous that was for decades,” reflected Greenwell, “not until I started teaching high school myself and realized how exhausting a day of teaching was.” He went on: “It was the first time an adult had treated me as though my life might have value.” The teacher not only spent time working on Greenwell’s voice but also ingrained in him a love for classical music. “What I heard in that music, what I still hear in it, was the possibility of a different world.”

At around the same time, Greenwell came across a book called “Giovanni’s Room” by James Baldwin, which explores themes of love, sexuality, identity, and shame. Despite the story ending in — spoiler alert — death and devastation for most of the characters, Greenwell said this book “saved his life.” It provided him with possibilities for a life that he had not yet considered. It “reoriented” his dignity. He read from the novel and then from his own essay about Baldwin’s work.

He concluded the lecture circling back to his message about art and failure: “Being a writer means failing every day … Striving each day to fail slightly less fills my life up with value,” he said. “I feel grateful every day that as a young person … I fell in love with art. … My hope for you is that you will discover what you love and that you will be courageous enough to live your lives in its light.”

Watch the assembly