Given that she didn't start to fly until age 41, you might not expect Ruby Wine Sheldon to have been a pioneering helicopter pilot. A professional photographer, she had moved to Phoenix in 1949 at age 32 to soothe her respiratory problems. The desert agreed with her; she took her first flying lesson in 1958.
After several years of instructing for Sun Valley Air Service at Phoenix Sky Harbor International Airport, Sheldon had to take a temporary retirement from teaching because she strained her vocal cords making herself heard in noisy cockpits. During her time off, she earned her initial rotorcraft rating, which she added to her commercial certificate and airplane and instrument instructor ratings.
Sheldon obtained employment with the United States Geological Survey's (USGS) Remote Sensing Unit. The unit flew aircraft platforms for cameras and imaging instruments to collect data on the country's water resources.
Sheldon soon checked out in most of the unit's aircraft. She flew the H-19 on floats for ecological studies in Louisiana and Florida, and a Lockheed T-33 to map the hydrology of South Florida. The Douglas B-23 Dragon was another airplane on the USGS roster, and to fly the twin-engine bomber, Sheldon obtained her type rating in a Douglas DC-3, because there were no training courses available in the B-23 at that time. Sheldon was classified as a "physical science technician," not as a pilot, because of the gender bias still in place at the agency during the 1970s, according to Sheldon.
After her retirement from the USGS in 1976, Sheldon returned to charter (in Cessna 310s and 421s) and air ambulance flying, and to instructing, which this 15,000-hour pilot still practices occasionally at age 89. She flew in the Powder Puff Derby (a now-defunct transcontinental air race for women) three times, and has flown the Air Race Classic (which succeeded the Derby) 22 times. She and race partner Marge Thayer have won the race three times, placed in the top five six times, and completed the ARC together again in 2006.