Michael grew up in Cary, North Carolina playing for CASL youth soccer club and Carolina Railhawks PDL. From 2005-2008 he attended and played soccer for the University of North Carolina at Chapel Hill. After college, he had an eight-year professional playing career in the USL, two for the Austin Aztex and six for the Richmond Kickers. In his final two years as a player, he served as the club captain as well as a player/assistant coach in his final year.

After retiring from playing after the 2016 season, he joined the Richmond Kickers Pro Team coaching staff as an assistant from 2017 to 2018. He began his youth coaching career in 2013 with the Richmond Kickers Youth Club, coaching in their Classic and Elite programs. 

ECNL coach Michael Callahan earned his US Soccer A-Youth License in early 2020.