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Does the phenomenology of human evil indeed attest to the correctness of the Freudian pessimistic thesis concerning man’s tragic fate within the civilization that he himself had built? To answer this crucial question this study has a two-fold intention: (1) To pose vis-à-vis Freud’s pessimistic thesis an optimistic alternative: one that dares to offer the abandonment of evil as the explanation of man’s nature, and the return to a vision of human solidarity, ethical responsibility, and the faith in good; (2) To trace Freud’s struggle against his own optimism. The study would propose a novel synergy between psychoanalytic self psychology and the Buddhist dharma in order to illustrate the existence of a vertical split within the core of the colossal essay of Civilization and Its Discontents, which reflects Freud’s own emotional and intellectual distress between his manifest psychoanalytic pessimistic world-view, and his profound humane understanding of transcendental horizon of optimism. The transition from civilization of pessimism to the culture of compassion will be presented as a transition of the psychoanalytic domain from metaphysics of knowledge to metaphysics of presence.