In 1997, Cary joined the faculty at a private boarding school in New Hampshire, where he serves as a college counselor and teaches 10th and 11th grade students part-time.
In 2006, Cary earned an M.A. in English Literature from Middlebury College, with a concentration in early 20th-century British literature while studying for three terms at Oxford University's Lincoln College. His graduate coursework focused on Shakespeare, Virginia Woolf, James Joyce, Toni Morrison, and William Faulkner — authors who still influence his writing today.