Tomlinson graduated from the Naval Academy in 1917 and became a naval aviator shortly after the conclusion of World War I. In the 1920s he was very much his own man, defying both official regulations and abominable flying weather. His descriptions of flying through ice, fog, rain, and other hazards explain why he put so much emphasis on the importance of instrument flying in its fledgling years. In 1928, while in a fighter squadron, Tomlinson organized the Three Seahawks, the Navy's first aerobatics team. Stifled by Navy bureaucracy, in 1929 Tomlinson resigned from the service and went into the commercial airline business. Employed by a predecessor company of the present TWA, he worked closely with Douglas Aircraft in the development of specifications for the DC-1. He also did test-pilot work for the Army in the 1930s and then was called back to active duty by the Navy for World War II. He became commander of the Naval Air Transport Service Pacific, which transported people and supplies throughout the theater. In the late 1940s, working with the Air Force, he had a role in the Berlin Airlift.