During World War II, Olson graduated from the United States Navy Japanese Language School in Boulder, Colorado.
He served in naval intelligence as a lieutenant with the Pacific Fleet Radio Unit, Station HYPO, at Pearl Harbor, Hawaii.
After the end of the war, Olson worked at the Central Intelligence Agency in Washington DC between 1948 and 1950, and he served as cultural attaché at the American embassy in Manila, Philippines from 1951 to 1952, before finishing his PhD at Harvard.
In 1955, he joined the American Universities Field Staff, an educational foundation dedicated towards providing in-depth studies of contemporary foreign society.
He continued his scholarly work after retirement, and his new book, Ambivalent Moderns: Portraits of Japanese Cultural Identity, was published in the month he died.