Of all the great novelists of the twentieth century, the German writer Hermann Hesse is arguably one of the most important for educationists. Education is a key theme in a number of Hesse’s novels and short stories. Beneath the Wheel (Hesse, 1968a) and Demian (Hesse, 1999) focus on school experiences, while Narcissus and Goldmund (Hesse, 1968b) is in part concerned with learning and teaching in a cloister school during the Middle Ages. More broadly, Hesse’s published work is united by a lifelong concern with processes of inner growth. Hesse is one of the finest exponents of the German tradition of the Bildungsroman: the novel of education as formation or development (Swales, 1978; Peters, 1996). Siddhartha (Hesse, 2000a), with its systematic account of the spiritual journey of its central character, provides a good example of Hesse’s contribution to this genre, as does the early novel Peter Camenzind (Hesse, 1969). Perhaps the most significant educational work in Hesse’s corpus, however, is his last and longest novel, The Glass Bead Game (Hesse, 2000b). First published (as Das Glasperlenspiel) in 1943, The Glass Bead Game marked the end of a long and difficult process of composition. Hesse worked on the book for more than a decade (Field, 1968; Mileck, 1970). Three years after the initial publication of the book Hesse was awarded the Nobel Prize for Literature. The first English translation of the novel was released under the title Magister Ludi in 1949. The second and more widely cited English version, translated by Richard and Clara Winston, was published in 1969. The main part of the novel focuses on the life of Joseph Knecht, who grows up in Castalia, a ‘pedagogical province’ of the 23rd century. The highest cultural achievement of Castalia is the Glass Bead Game. The Game remains somewhat mysterious, but readers learn that it blends aesthetic, intellectual and meditative elements, and allows participants to play with the total contents of culture. It is a means for linking all disciplines; a kind of universal language. Knecht rises through the elite schooling system, becomes a member of the Order of the Glass Bead Game, and is eventually appointed to the exalted position of Magister Ludi (Master of the Game). Along the way, however, he questions aspects of Castalian life, his doubts ultimately leading to his unprecedented decision to resign his post as Magister Ludi in favour of a quiet life as a private tutor. The main story of Knecht’s life is preceded by the narrator’s brief history of the Game and followed by a set of poems and three fictional autobiographies or ‘Lives’ (presented as posthumous writings from Joseph’s student days).This paper considers The Glass Bead Game from an educational point of view. I argue that in the life of Joseph Knecht a profound process of educational transformation becomes evident. Knecht himself conceives of this as a form of ‘awakening’. The paper analyses Knecht’s transformation in the light of Paulo Freire’s theory of education. Knecht develops a critical consciousness, becoming, over time, less certain of his certainties, more aware of his own incompleteness, and increasingly convinced of the importance of teaching. Dialogue plays a key role in the development of Knecht’s critique of Castalia and his understanding of himself and his vocation as a human being. The paper falls into four main parts. The first section details key moments and figures in Knecht’s educational life. This is followed by a closer analysis of the dialogical bond that develops between Knecht and two other characters, Plinio Designori and Father Jacobus. The third section discusses the relationship between conscientisation and contemplation for Knecht and others in Castalia. The final part reflects on the significance of death as a theme in the novel and considers some of the educational implications arising from this.