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Starting from Freire’s Pedagogy of Freedom, this paper investigates the internal limit of education’s self-knowability. Freire’s reflection on the necessary “falling short” of pedagogy opens new entry points for examining the position of psychoanalysis in the foundations of education. Freud’s claim is considered: that he called both psychoanalysis and teaching “impossible” professions had to do with the fact that both suffer doubt over their possibility as knowable endeavors. For Lacan, the impossibility for psychoanalysis to fully know itself is founded on the nature of what it deals with: the unconscious. As Lacan suggests, the unsuccessful act successfully discloses the unconscious as the gap or discontinuity that gives shape to the act. Following Lacan, this paper defines the shortcoming of pedagogy as the condition of its successful encounter with the unconscious. I claim that critical pedagogy works by radicalizing the unknowability of education in the effort to disrupt its own unfolding.