This article evokes the itinerary of a young man who was finding it difficult to separate from his parents and under the sway of an aunt; he was hospitalized in a psychiatric unit and tempted by radical religious commitment. What paths towards the freedom of thinking and acting were open to him? Looking at the obstacles to psychic freedom is the main focus of this reflection. This leads to an examination of the paradoxical relationship between psychoanalysis and freedom, far from the illusion of absolute freedom of the notion of free will in the classical philosophical conception of the subject. Psychoanalytic conceptions of remembering, Lacanian elaborations, and thinking about subjectivation are evoked before moving on to more clinical remarks which emphasize the importance of aggression and creativity in the process of “becoming oneself”. A mapping of paths is thus outlined along which psychoanalytic experience manifests its liberating potentialities.