Massey studied at the Chicago Academy of Fine Arts; graduated in 1954. As a student Massey was assigned to assist Armin Hofmann and Josef Müller-Brockmann at the 1953 Aspen Design Conference. He abandoned his initial plan to become a political cartoonist and became an idealistic yet pragmatic designer and design director who served for decades with ever increasing responsibilities at the Container Corporation of America and its Center for Advanced Research in Design (CARD), which he founded. He was a book designer and art director, working for Ralph Eckerström, who invited him in 1957 to become a graphic designer at CCA under Herbert Bayer (1956–65). His principle was: ‘Be classical or extraordinary; nothing else is acceptable’. He left CCA (1983) and established his design consultancy. Massey taught at the University of Illinois (1984), and became a full professor in 1986. He has won awards from NSAD, NY ADC and the Leipzig Book Fair, and received the distinguished AIGA Medal in 1994.