The term workadaddy was originated by Tom Wolfe during the sixties. Personally, I first came across it while reading "The Electric Cool Aid Acid Test," though this may not have been the first use of the term.
My take on workadaddy was that it referred to the “squares” that didn’t get involved during the counter revolution of the sixties. These working men stayed in their suits and keep their jobs and went home at night to their fifties-era families. These were the men who didn't get it.
Of course, if Tom Wolfe or anyone else who was part of this world wants to correct me on this interpretation I am open to hearing about it.