Oakley taught theater and English at Loveland High School, Colorado from 1965 to 1968.
From 1967 to 1970 his career as a director and actor included Buckskin Joe in Cañon City, Colorado (1967); the Red Ram in Larimer Square, Denver (fall and winter 1969); the Oxford Hotel, Denver; and the Iron Springs Chateau in Manitou Springs, Colorado (1968, 1969, 1970) .