Clifton Olesen was born in McGregor, Iowa on August 7, 1899 to Ben and Nellie Olesen. During World War I, Olesen served in the 38th Aero Squadron. Upon returning to the United States, he spent two years as an exhibition flyer.
As exciting as exhibition flying could be, it was not a steady paycheck. Recently married, Olesen needed a regular paying job. He joined the Air Mail Service on March 5, 1921.
The demands of airmail work were too much for Olesen's skills, and he left the service after about seven months.