The article focuses on three biographies of Josef Knecht from the novel by Hermann Hesse “The Glass Bead Game” with regard to the postulates of transpersonal psychology. A thorough study provides insight into the peculiarities of a unique literary technique – the transfer of the “self” into different historical periods by means of imagination, as a kind of “way to self”, devotion to truth through pagan voluntary sacrifice (“Rainmaker”), the ascetic self-denial of a Christian schemamonk (“The Father Confessor”), the life of an Indian ascetic (“Siddhartha”), understanding that all being is illusionary. The research highlights the similarity of plot events, names, integration of esoteric and exoteric perspectives. The study reviews a holotropic state of consciousness, which can develop into psychoid experience, accounting for the impossible to become possible. Based on the judgments of the direct relationship between the concepts of the macrocosm and the microcosm, the perception of reality as a result of human intellectual activity, it is specified that the efforts of the “possible human”, “virtual human” to liberate themselves from the dualistic perception of reality is accomplishable by acquiring the unity of consciousness. The authors point out that the review of the motive of “awakening” indicates Hesse’s intention to embody absolute transcendent reality in his characters, which could manage the crisis of splitting consciousness.