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Abstract: The functions of the initiation plot in the novel by L. N. Tolstoy “The Cossacks” are considered in the artistic paradigm of the archetype of the Fool – one of the key figures of a folk tale whose traits are clearly readable in the structure of the character of Dmitry Olenin. Reconstruction of a number of archetypical models in the character’s life and spiritual biography reveals symbolic parallels with traditional fairy tale motifs: the search for happiness and the “other kingdom”, the story of looking for a bride, the motifs of trials and subsequent transformation, and the mythologem of the Path of life. The analysis of the artistic system of the work also allows one to see the dialogic interrelations of the initiation myth with other mythological texts: the totem myth, the felicity myth, etc. At the same time, in the logic of Olenin’s fate and the vicissitudes of his path of life, we find inversions of universal mythopoetic schemes, primarily in the structure of the initiation plot itself. If the fabulous Fool (Blunderer / Simpleton as his invariants) reaches his goal, the main character of “The Cossacks”, having passed a series of Initiations and having experienced spiritual renewal, in the finale of the work loses his “earthly” happiness and remains in the situation of incomplete personal development. The study leads to the conclusion that the fundamental difference between Tolstoy’s understanding of the path of initiation and the archaic-mythological and folklore fairy-tale original characters lies in the fundamentally incomplete nature of the former. The transformation of Tolstoy’s character is never uniquely final; one of the forms or one of the initiation modes can be completed, but not the Path itself. In this, Tolstoy’s interpretation of the dynamics of the human fate converges with the logic of the mystery Initiations. The open finale of “The Cossacks” testifies to the ambivalent “unity of opposites” of the plot of the Fool’s initiation in the narrative of Tolstoy and in the traditional fairy-tale narrative.