* 1992 to 1997: Olson served as a trial attorney and later Deputy Director of the National Church Arson Task Force in the United States Department of Justice Civil Rights Division
* 1994 to 1997: Olson worked part-time as an adjunct professor at George Washington University Law School
* 1997: Olson joined the Office of the United States Attorney for the District of Idaho
* 2010: Olson rose to the rank of Senior Litigation Counsel
* 2017: Olson resigned
* 2017: Olson joined the Boise office of Stoel Rives, a law firm that operates in the Pacific Northwest
* 2021: Olson was included on a shortlist of possible nominees to succeed Judge B. Lynn Winmill