Sherman is a graduate of Oley Valley High School (1981), and Penn State University (Journalism, 1986) where he was a sportswriter on the Daily Collegian. He worked at three newspapers in southeastern Pennsylvania and won more than a dozen journalism awards (Reading Eagle; The Evening Phoenix, Phoenixville; The Mercury, Pottstown) before becoming a teacher in 1998. He was an eighth-grade language arts teacher at Daniel Boone Middle School in Douglassville, Pennsylvania for 23 years. Sherman was diagnosed with MS in 2002.