Goethe’s last novel, ‚Wilhelm Meisters Wanderjahre‘ (‚The Journeyman Years‘, 1821/29), which seriously challenged the mindset of its contemporary readers is nowadays being understood as a window to literary modernity. The open and manifold process of signification which, according to modern literary criticism, constitutes the narrative strategy of the text can be aptly tested by analyzing its seemingly ‘traditional’ initial episode entitled “Saint Joseph the Second”. Read in conjunction with further textual references in the novel itself as well as against the background of relevant literary and cultural contexts this episode shows a path leading to typically modern answers pertaining to the author’s ‘most famous question’, which is quoted in the above title. An important thematic and intertextual repercussion of Goethe’s novel in the 20th century, Hermann Hesse’s novel ‚The Glass Bead Game‘ (1943), both confirms and complements this reading.