Instead of entering college after graduating in 1939, Olds enrolled at Millard Preparatory School for West Point in Washington, D.C., a school established to prepare men for the entrance examinations to the military academies. When Germany invaded Poland, Olds attempted to join the Royal Canadian Air Force but was thwarted by his father's refusal to approve his enlistment papers. Olds completed Millard Prep and applied for admission to the United States Military Academy at West Point. After he received a conditional commitment for nomination from Pennsylvania Congressman J. Buell Snyder, Olds moved to Uniontown, Pennsylvania, where he lived in the YMCA and supported himself working odd jobs. He passed the West Point entrance examination and was accepted into the Class of 1944 on June 1, 1940. He entered the academy a month later but after the Japanese attack on Pearl Harbor, Olds was sent to the Spartan School of Aeronautics in Tulsa, Oklahoma, for flight training. This training ended a year later by Christmas 1942. Olds returned to West Point, hoping to graduate early and see action in the war.