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The author discusses various relationships derived from the image of gap, precipice, and abyss with specific emphasis on interacting dynamics between being and knowing as explicated in the Zen Buddhist teachings of Hui-neng and in the psychoanalytic writings of Wilfred Bion. While of significant value to psychoanalysis, it is argued that symbolic meanings can occlude the actuality of the analysand's or of the spiritual seeker's affective experiencing, particularly concerning the human tendency to concretize experiential states engendered through meditation and/or the psychoanalytic encounter. The author draws from Matte-Blanco's explication of symmetrical and asymmetrical perceptual modalities to discuss the fluid nature of spiritual experiencing, paradoxical coexistence of ultimate and relative realities and reciprocal dynamics and identities between states of experiencing that might otherwise appear opposed. The primacy of experiencing for both disciplines, particularly concerning the experiencing subject's momentary state of consciousness, forms a central theme for both Zen and psychoanalysis. Brief clinical vignettes support and illuminate the author's points.