Sale worked initially in journalism for the leftist journal "New Leader", "a magazine founded in 1924 in part by socialists Norman Thomas and Eugene Debs," and the "New York Times Magazine". He then became a freelance journalist. He spent time in Ghana and wrote his first book about it. His second book, "SDS", was about the radical 1960s group Students for a Democratic Society, of which he was a founder. The book "is still considered one of the best sources on the youth activist organization that helped define 1960s radicalism." In 1968, he signed the “Writers and Editors War Tax Protest” pledge, vowing to refuse tax payments in protest against the Vietnam War. 