Although Richard won a scholarship to Pratt and briefly attended the University of Michigan, he was mainly a self-taught designer. His first experience was at the Palmer Paint Company, where he painted originals for the first paint-by-number sets. In 1955, at the age of 21, he became art director at Walter J. Thompson. It took him 11 years, working at various agencies, before he started his own Hess Design, a graphic and film art consultancy. Hess was an influential graphic designer who worked on annual rapports, corporate magazines and identity systems for clients including Champion International, AT&T and Washington Post. He also worked for CBS, PepsiCo, IBM, Xerox, DuPont and Esquire, New York magazine and the New York Times. When he was designing Vista for the United Nations, he started to illustrate, something he hadn’t done for 17 years. His chief pleasure was painting covers for Time, featuring famous but some times controversial figures.