Two case vignettes illustrating different ways of listening to clinical material are presented. The author discusses some limitations of clinical psychoanalytic theory that stem from the fact that primary unconscious processes are, by their very nature, impossible to describe in a language regulated by secondary processes. Hegelian dialectics, first addressed in psychoanalysis by Lacan and later elaborated in the work of Green, as well as the use of paradox by Winnicott and the formalistic approaches of Matte Blanco and Bion, are briefly reviewed as alternative formulas. As psychoanalysts, we are condemned to live with doubt, and neither clinical theories nor metapsychology offer escape from this reality.