Founder of Q methodology and advocate of a science of subjectivity, William Stephenson on numerous occasions attested to a life-long interest in education. Being too young at age 17 to go to university, he was a pupil teacher before beginning his studies for his bachelor’s and master’s degrees in physics, subsequently completing a Diploma in the Theory and Practice of Education while studying for his PhD in physics at the University of Durham. After moving to University College London to undertake a second PhD in psychology, he attended classes with Sir Percy Nunn, one of the UK’s leading educational theorists. In this chapter, the wide range of Stephenson’s substantive interests in education are identified; focus is then directed to Stephenson’s two most important contributions to education: his first book Testing School Children, which was critical of the selection procedures adopted in the UK’s post-World War II educational policy; and his unpublished Quiddity College, ostensibly a blueprint for an ideal college of higher education based on Stephenson’s unique experience of English and American education. The significance of some of Stephenson’s ideas about the cultivation of subjectivity in both the school classroom and college/university environment is also assessed.