Olson enlisted in the United States Air Force in 1979. She was the first womanto go through flight training at Laughlin Air Force Base and became one of the first female pilots in the Air Force. She served as a squadron commander of the 96th Air Refueling Squadron out of Fairchild Air Force Base, becoming one of only eight female squadron commanders. Olson reached the rank of colonel in 2000, and was assigned to the comptroller's office in The Pentagon in early 2003. In 2003, General Jay Garner, the director of the Office for Reconstruction and Humanitarian Assistance, selected Olson to be his executive officer in helping to rebuild Iraq after Operation Iraqi Freedom. Three months into the role, Garner was replaced by Paul Bremer, and the Department of Defense charged Olson with providing improper assistance to a private security firm from South Africa. Though she denies the allegations, Olson accepted a non-judicial punishment rather than face a potential court martial by pleading guilty to minor administrative violations and accepting a reprimand. She was allowed to retire with an honorable discharge without a reduction in rank, which she received in May 2005. After her discharge, Olson founded Grace After Fire, a nonprofit organization that aids female military veterans when they return to civilian life. She also wrote a memoir, Iraq and Back: Inside the War to Win the Peace, which was published in 2006.
Politics
In 2007, Olson became the Director of Human Resources for the Dallas Independent School District. That year, she was elected to the school board of the Weatherford Independent School District, representing Place 3. She resigned her seat, effective September 1, 2011, because she and her husband decided to move out of Weatherford, which made her ineligible to serve on the WISD school board. In the 2018 elections, Olson ran as a Democrat against Sid Miller for Texas Agriculture Commissioner. Miller defeated Olson in a close election. Olson ran for the United States House of Representatives in in the 2020 elections. She advanced to a runoff election against Candace Valenzuela for the Democratic nomination. Olson was defeated by Valenzuela in the runoff.
Personal life
Olson met her husband, Kent, while they both served as flight instructors for the Air Force in Arizona. They have two daughters, and live on a farm in Mineral Wells, Texas. Olson is a Master Gardener. In 2014, she was inducted into the Texas Women's Hall of Fame.