This paper introduces the subject of courage into the psychoanalytic discourse about masochism and also demonstrates that ordinary ethical and axiological concerns can and should be included in our psychoanalytic language and practice. At each stage of a psychoanalysis, it may be helpful to consider whether the patient's experience might be that taking a step deeper into the psychoanalytic relationship is both courageous and masochistic. This consideration can open the door to exploration of conscious beliefs and how they are related to unconscious fantasies and assumptions. Considering the possibility that even a sadomasochistic enactment may simultaneously represent a courageous attempt to rework conflict or trauma can enrich the way analysts listen to both manifest and latent material.