This paper has as its focus the life and thinking of the educational theorist and schoolmaster J. H. Simpson (1883-1959), who was not only a reforming teacher at Rugby School but was also the first headmaster of the progressive Rendcomb College. His ideas around education were outlined in a number of books. At the heart of his thinking lay concerns around democracy and self-government and the article explores how these were enacted at various points of Simpson's life with a particular focus upon his work until 1932. Attention will be paid to how his thinking evolved, moving from simple democracy in the classroom to wider decision-making within an entire school. Linked to these concerns were a number of curricular initiatives that sought to offer a point of contrast to more traditional public schools. The article will conclude by attempting to offer consideration of the legacy of Simpson's ideas.