[1] During World War II he served as an ambulance driver in North Africa for the American Field Service and then as a flight officer with the U.S. Army Air Force from 1943 to 1945.
He wandered incessantly, usually by car, preferring temporary marginal jobs of all kinds ― such as migrant farm worker, driver, ice cream seller, door-to-door market researcher — providing much of the experiences and detail of his fiction.
In 1955 Robert Creeley published Woolf's first short novel, The Hypocritic Days with Divers Press, and Woolf would be often associated with the fiction wing of the New American Poetry, appearing in the anthologies The Moderns: An Anthology of New Writing in America (1963), edited by LeRoi Jones (Amiri Baraka) and New American Story (1965), edited by Donald M. Allen and Robert Creeley.
In 1976 he married his second wife, Sandra Braman, with whom Woolf ran a small press, Wolf Run Books, as well as short lived little magazine, Vital Statistics (3 issues, 1978–1979).
[2] Woolf's novels are typically road narratives, whose protagonists seek an existence outside the encumbrances of material needs and middle class expectations.