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The psychoanalytic journey and the psilocybin journey both reveal unconscious dynamics. In this article a psychoanalyst discusses his own psilocybin journey. Similarities and differences between these journeys are discussed. Possibilities are offered for a dialogue in which psilocybin may contribute to psychoanalytic understanding and psychoanalysis may contribute to the understanding of psychedelic sessions. Patients may benefit from this cross-fertilization.