[3] Subsequently unable to continue with his studies, Flynn dropped out of school and ended up working at the Pine Street Inn, a homeless shelter in Boston.

The following year he was awarded a fellowship at the Fine Arts Work Center in Provincetown, Massachusetts, where he became friends with Jacqueline Woodson, Tim Seibles, Paul Lisicky, Mark Doty, Stanley Kunitz, Alan Dugan, Carl Phillips, and others.

[citation needed] From 1992 to 1999, he was a member of the Teachers College Reading and Writing Project at Columbia University, in which he served as an educator and consultant in New York public schools.

[7] Since 2004, Flynn has been a Professor on the Creative Writing faculty at the University of Houston, where he is in residence each Spring, teaching workshops in poetry and interdisciplinary / collaborative art.

It is a hybrid of several genres, including memoir, fairy tale, theater, police reports, poetry, essay, speculative fiction, and magic realism.

Stay: threads, conversations, collaborations (2020) gathers together 30 years of Flynn's writing, alongside his collaborations with artists, including Jack Pierson, Catherine Opie, Kevin Jerome Everson, Sarah Lipstate, Paul Weitz, Rachel Eliza Griffiths, Sarah Sentilles, Amy Arbus, Ryan McGinley, Zoe Leonard, Mark Adams, Bill Schuck, Guy Barash, Mel Chin, M. P. Landis, Jared Handelsman, Alix Lambert, Gabriel Martinez, Douglas Padgett, Kahn & Selesnick, Josh Neufeld, David Brody, Daniel Heyman, Mischa Richter, Jim Peters / Kathleen Carr, and Marilyn Minter.

His readings on neuroscience and memory, including books by V. S. Ramachandran, David Eagleman, and Antonio Damasio, helped him to comprehend his experience of being on set for the reenactment of his mother's death by Julianne Moore.

Another Bullshit Night in Suck City (2004),[11][12] a New York Times Bestseller, won the PEN/Martha Albrand Award for the Art of the Memoir, was a finalist for France's Prix Femina, and has been translated into fifteen languages.