This paper considers Hermann Hesse’s novel, The Glass Bead Game, in the light of Paulo Freire’s educational philosophy. The Glass Bead Game is set in Castalia, a “pedagogical province” of the 23rd century. It is argued that the central character in the book, Joseph Knecht, undergoes a complex process of conscientisation. Knecht develops an increasingly critical understanding of Castalian society, questioning some of its most cherished assumptions while nonetheless deepening his appreciation of the beauty of the Glass Bead Game. He becomes less certain of his certainties as he grows older, and eventually decides to give away his prestigious post as Magister Ludi (Master of the Glass Bead Game) to pursue a quiet life as a tutor. Dialogue plays a key role in the development of Knecht’s critical consciousness. Freirean theory is seen to provide a robust framework for the analysis of key themes in Hesse’s text. At the same time, The Glass Bead Game is helpful in demonstrating the meaning and significance of conscientisation and dialogue for educational lives.