The author refers to the actual modern philosophy of people in the optimistic perspective of their personal development built on the methodological possibilities of the existential-humanistic approach. Overcoming objectivism and psychological naturalism in understanding the essence of man in the spirit of optimism is possible only in existential philosophy, transcendental phenomenology, humanistic psychology and pedagogy, through the creative and semantic activity of consciousness. The author examines the evolution of the ideas of existential subject-philosophy focused on the issues of freedom and responsibility, which revealed the ontological significance of “living unique subjectivity” in the works of M. Heidegger, K. Jaspers, J.-P. Sartre, V. Frankl, E. Fromm, K. Rogers. Based on the existential analytics of a person the author reveals the fact that the humanistic ideas of this direction based on the ideas of freedom, «being-without-support», are ultimately shaped by the principle of optimistic perspective and faith in Man in the humanistic pedagogy of A. S. Makarenko and V. A. Sukhomlinsky; the normativity of the universally valuable things. In conclusion, specific findings are presented about the methodological significance of the existential-humanistic approach in the modern philosophical conceptualization of paradoxical optimistic faith in a person, his optimism (Sartre’s heroic optimism, Makarenko’s courageous optimism, Frankl’s tragic optimism) as a perception of life based on the philosophy of responsibility and overcoming difficulties on path to success. A person must see himself in the perspective of opportunities, then he will have a positive freedom to choose and bear responsibility.