The article is an attempt at a philosophical interpretation of the literary text. Its task is to identify the principles of the human self, which are presented in classical literature, in Homer’s “Iliad” and “Odyssey” and Dante’s “Divine Comedy”. The study provides an analysis of the archetypal narrative structure to which the model of human development with three components (individual, person, personality) is applied. The correspondence of the heroes to this typology, which is not the final measure of the human, but resembles the “ideal types” according to Max Weber, has been traced in the research. The dynamics of the development of the inner world of a human being, which corresponds to the plot of the journey, is analyzed. That is not a journey only in physical space, but an inner path too that a person overcomes in a gradual process of self-awareness. It has been found that the works of Homer and Dante can be interpreted as not implying a developed and independent personality. On the other hand, the characters demonstrate the key factors of change that occur within the one who forms the traits of self-sufficiency. The study succeeds in constructing a psychological map that allows outlining not a stable type, but rather different personality horizons. There are certain human aspirations of the man to be the creator of the self. However, such motivations involve not only a number of arbitrary manifestations of human beings but also the establishment of a measure for themselves. Initially, these intentions are carried out without self-absorption, reflection, and self-assessment. After all, unrestrained and unbalanced human temperament for a long time remains subject to higher (divine) forces and is significantly limited by this supreme power. Nevertheless, a human eventually comes to the need for self-knowledge and establishes a balance between rational and unconscious manifestations. People succeed in getting out of the circle of self-forgetfulness by overcoming various forms of alienation, loneliness, narcissism, self-contradiction, negligence, arrogance. Self-control is achieved by truth about oneself, overcoming fear, recognizing the effects of temptation and passion. The human attitude to the Other becomes possible due to freedom and love as cardinal manifestations of the active component of the self