Jessen worked throughout her career as a flight instructor, demonstration pilot, advisor to the Federal Aviation Agency (FAA) and president of the Ninety-Nines.
[6] During that time, she joined the Civil Air Patrol, where one of the students she flew with allowed her to fly the plane sometimes and told her that she was a "natural.
"[7][8] Jessen attended Oklahoma University (OU), where she continued to fly and also played cello in the school's symphony orchestra.
[5] After passing the tests, Jessen was invited to participate in the next round of evaluations held in Pensacola, Florida.
After her boss disapproved her request to travel to the next phase of testing, quit her job as a flight instructor.
[17] She later embarked on a 90-day cross-country flight with fellow pilot, Joyce Case, in a Beechcraft Musketeer airplane.
[5] Jessen was on the women's advisory committee to the Federal Aviation Agency (FAA) and had been appointed by President Lyndon B.
[22] In 2017, Jessen began to experience macular degeneration in her left eye and was forced to stop flying.