In all of his work Hesse has concerned himself with the individual and his quest for meanings in life. For Hesse the forms of the society which surround the individual are meaningless; therefore, the individual becomes the outsider, the Hessean hero who asks, "How shall I live?"… Although, then, the theme of the outsider underlies much of Hesse's work, there are three novels which, it seems to me, stand out as signposts, marking the direction of Hesse's thinking in terms of an outsider concept, in terms of the nature of such a being. First, Unterm Rad depicts the making of the outsider, the development of his awareness of the social organism and his separation from it, his becoming an isolated cell. In Demian a later stage of the outsider appears: the outsider develops in his isolation, achieves independent life (a stage sometimes known as the break-through). Hesse's "Bible" for the outsider, then, is Der Steppenwolf, in which he prescribes a way of life for the full-fledged outsider and gives him his reason for being. (p. 172)
[Unterm Rad] concerns a schoolboy Hans Giebenrath and his struggle with the world in which he lives. It is his father's world, the world of middle-class society which respects money, respectability, and God (from a distance). Hans performs well in school and as a reward is going to be allowed to become, at state expense, a theologian. But Hans already has the mark of the outsider (the mark of Cain): the awareness that he is something other, something better than his well-fed, carefree friends…. However, Hans does not resist being led down the first few steps of the well-defined path which leads the brilliant offspring of the middle class to a safe and respectable career in the church; he goes to the seminary at Maulbronn on a scholarship…. Here spirit and intelligence are oppressed, crushed under the wheel. Here manifests itself the conflict between the professors and the bright student, between society and the gifted individual, between the Philistines and the artist: the school relentlessly seeks to root out the few extraordinary students who chance to appear and to nip in the bud any outgrowth of spirit…. Schools, for Hesse, make no provision for the growth of the individual; they strive, rather, to restrict growth to the group level. And, as far as Hesse is concerned, only the individual and his growth matter…. [Hans Giebenrath's] inner revolt is manifested in his friendship with a dangerous fellow-student, Hermann Heilner, actually a Doppelgänger [double] (he is the "healer" and also H. H., Hermann Hesse), one of that kind with which Hesse surrounds his heroes and with which he populates his novels. Heilner brings open revolt into the scope of Giebenrath's thinking. Heilner does not try to conform. He struggles against the yoke of the bourgeois educational system and for a moment (three days actually) breaks free. Heilner's escape from the school is thwarted; he is returned. His father then takes him home, and Hans Giebenrath hears no more of him. This episode in Unterm Rad marks the birth of the outsider. The example of Heilner convinces Hans that he, too, cannot exist in the fold, that he has, because of his very nature, been shouldered out of it, and that he must acknowledge and live with the fact of his isolation. The sadness in the book comes from the ending…. [As the novel focuses] on the last year in the life of Hans Giebenrath, it becomes the story of an individual who became an outsider, and it tells of his sadness at being an outsider and of his failure to make something valid of the role.
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