Fussman started his career as a sportswriter for The Miami Herald and The St. Louis Post-Dispatch, then moved to New York, where his work appeared in the magazines Inside Sports and Sports Illustrated.[3] He learned how to interview on trains and buses, when he travelled around the world for 10 years and was constantly in conversation with people from all cultures and walks of life.[2] Fussman's writing during this time and thereafter often revolved around quests.
Fussman began contributing to Esquire when David M. Granger took over as Editor in Chief in 1997. He became the lead interviewer for the magazine's "What I've Learned" column, in which people who have lived extraordinary lives discuss the wisdom they have accrued. Some the "What I've Learned" column, have reissued in two books titled The Meaning of Life,.[2][4]The Austin Chronicle has described Fussman's work in this format as "peerless" and "prolific".[4]