Wittgenstein explores learning through practice in the Philosophical Investigations by means of an extended analogy with games. However, does this concern with learning also necessarily extend to education, in our institutional understanding of the word? While Wittgenstein's examples of language learning and use are always shared or social, he does not discuss formal educational institutions as such. He does not wish to found a ‘school of thought’, and is suspicious of philosophy acting as a theory that can be applied to other areas of life. While Wittgenstein's focus on developing independent thinking was neither individualistic nor anti‐institutional, it did, however, focus on developing the thinking of his students rather than theorising about how this could be applied on a large scale. An analysis of Hermann Hesse's novel, The Glass Bead Game will help us to pick up where Wittgenstein deliberately left off—thinking about how (or if) one can institutionalise learning methods that encourage thinking for oneself. These differences in the writers’ treatment of education will become evident in the differences between their game analogies. While language‐games combat our ‘craving for generality’ in Philosophical Investigations, the Glass Bead Game represents this craving, and how it manifests itself throughout history in disciplines other than logic and philosophy of language. It also represents the potential for institutions to become insular, exclusive communities.