Prior to turning professional, Olson attended the Michigan Technological University where he played four seasons (2008–12) of NCAA Division I hockey with the Michigan Tech Huskies, where he registered 42 goals, 51 assists, 93 points, and 156 penalty minutes, in 127 games. Olson was named to the WCHA All-Academic team in both 2011 and 2012, and served as captain during his senior year.[1]
On May 28, 2015, the Florida Panthers re-signed Olson to another one-year contract.[3] Olsen suffered a dip in production with new Panthers' AHL affiliate, the Portland Pirates during the 2015–16 season. In 67 games, he contributed with 13 goals and 26 points.
As a free agent from the Panthers in the off-season, Olson left North America, signing a one-year deal with reigning Austrian champions, EC Red Bull Salzburg of the EBEL on July 15, 2016.[4] Olson demonstrated his versatility throughout the 2016-17 season with Salzburg, scoring 38 points in 39 games while playing in all situations defensively with the club.
On May 28, 2017, Olson opted to sign in the Neighbouring DEL, agreeing to a one-year deal with German club, ERC Ingolstadt.[5] On February 3, Olson scored the goal of the month by batting the puck out of mid-air from his defensive zone into the opposing team's net in the game against the Grizzly Adams Wolfsburg.
Olson played three seasons in Ingolstadt before leaving as a free agent to sign a one-year contract with Krefeld Pinguine on December 2, 2020.[6]