Fewing graduated from Highline High School in Burien, Washington, where he led the team to a state championship in his senior year.
[1][2] After briefly attending Green River Community College, Fewing played for two seasons as a member of the University of Washington Huskies team from 1983 to 1984.
[3] He spent most of his freshman season as a substitute player, but broke away to become a regular starter under coach Denny Buck as a goalscoring midfielder.
[1][8] After a failed tryout with the Tacoma Stars, he accepted an offer to coach the Seattle University Chieftains in 1988, taking over a program that had a losing record in eight consecutive seasons.
[22] Fewing joined the broadcasting team for Seattle Sounders FC, a new Major League Soccer franchise, for their inaugural season in 2009 as a television and radio analyst.
[1][24] Fewing was named the executive director of the Seattle chapter of America SCORES, a literacy and sports organization, shortly after leaving the Redhawks.
[25] Fewing was hired in November 2009 as the head coach of the Kitsap Pumas of the Premier Development League on a two-season contract.