Fairgrave graduated from St. Paul Mechanic Arts High School in 1920. She went to Curtiss-Northwest Airport and tried to find someone to take her up for a parachute jump. Ray Miller, one of the pilots there at the time, would not take her, but insisted she go home and strengthen her muscles. She took his advice, but returned, making her first jump from a plane flown by Vern Omlie, who would become her future husband. She made many jumps and performed wing-walking with Omlie on a barnstorming tour of the South. They married and Phoebe learned to fly. She was quite skillful and entered women's air races and cross-country tours, winning the Women's Air Derby from Santa Monica to Cleveland, and the Dixie Derby from Washington, D. C. to Chicago in 1930. From 1932 to 1936, she campaigned for President Roosevelt by flying around the country advertising and speaking on his behalf. He appointed her Special Advisor for Air Intelligence to the National Advisory Council for Aeronautics. She opened a flying school in Memphis and later joined the CAA, from which she retired in 1952.