The relation between literature and psychology is a complicated one. However, their connections can offer a psychologically effective interpretative frame with a potential psychological effect. In this sense reading is not only an aesthetic, but also a psychological process that can also be applied for bibliotherapeutic purposes. Hermann Hesse is a special case from two perspectives: 1. in biographical terms, as Hesse’s life itself was full of crises, which compelled him to undergo psychoanalytic and -therapeutic treatments. He finally managed to overcome his depression—a healing process that is mirrored in some of his literary works as well. 2. These works can thus be read as stories about psychological development, as a process of individuation corresponding to the psychology of Carl Gustav Jung (as in Demian), or about psychological healing from depression and even suicidal thoughts (as in Steppenwolf). Their characters often require from the reader, according to the tradition of the Bildungsroman leading back to Goethe, a deep identification, which can result in a positive psychological effect in the sense of a bibliotherapy. Thus, these works of Hesse’s are examples of the positive role of literature in a world in which depression constitutes a significant problem.