After finishing his M.A. in Journalism at Indiana University in 2005, Comiskey began his career writing for small publications such as the Bloomington Herald-Times and the Indiana University Alumni Magazine. For the past 12 years, he has worked at Indianapolis Monthly magazine, where he is currently the deputy editor. He has won more than a dozen Society of Professional Journalists Awards for his feature writing. In 2016, he also had the pleasure of serving as the adviser of The Butler Collegian.