Pedagogy and hierarchy are intimately connected. This book traces historical versions of the relationship between hierarchy and education through four key figures: Plato, Augustine, Abelard and Dante. Each provided canonical contributions to how hierarchies both work and fail in education: Plato through the ladder of beauty and the cave metaphor; Augustine through his Confessions; Abelard through his relationship with Heloise; and Dante through the Divine Comedy. All four worked within the tradition of a Great Chain of Being. Its basic premise was that there were qualitatively different orders of experience that needed to be described with the intent of pedagogically revealing to the reader how to travel through the varying stages. As such this tradition exists as one of the great repositories of hierarchical pedagogic practice in the West. This book is an introduction to the history of hierarchical teaching practice by describing various journeys of learning and discussing the techniques and paths used in the process.