Foreshadowing some themes of his later writing, he noted, "I grew up on a steady diet of SF and horror and ghost stories, and that’s still a love of mine," and that as a teenager he "was fascinated by the serial killer novels that were popular" in the 1980s.

"[5][6][7] As a thirteen-year-old, expanding on an assignment from his "really wonderful" seventh grade English teacher, Mr. Christy, Chaon wrote a fan letter to Ray Bradbury, and enclosed some of his own stories, "which were slavish imitations of Ray Bradbury stories."

Chaon said, "The amazing thing was that Bradbury actually wrote back to me, praising the stories and offering a critique.

"[5][6] Chaon earned a bachelor's degree from Northwestern University, where he originally intended to be a film major, in 1986.

His professors at Northwestern included Sheila Schwartz, whom he would later marry, and Reginald Gibbons, whom he described as a "lifelong mentor" and who later published Chaon's first book.

[1][5][6] After his family moved to the Cleveland area in 1990 when his wife was appointed to a teaching position at Cleveland State University, Chaon worked as a stay-at-home father and took on a number of odd jobs, such as catering, bartending, construction, and work as an administrative assistant, until 1996 when his first short-story collection, Fitting Ends, was published.

[8][5] Beginning in 1998, Chaon taught at Oberlin College, where he was the Pauline Delaney Professor of Creative Writing and Literature, before retiring in 2018.

[5][9][10][11] His former students include Ishmael Beah, Megan Kruse, Emma Straub, Rumaan Alam, Edan Lepucki and Lena Dunham.

He later said that, because his adoptive father was a construction worker and different in nature from Chaon, "I had this whole image of, if I were to ever find my biological parents, they would be very artistic.

[citation needed] The two met when he was a nineteen-year-old undergraduate student at Northwestern, and she was his thirty-year-old writing professor.