Arguing for a reappreciation of the aesthetic aspects of psychoanalysis in distinct contrast to psychotherapies that rely on a set of techniques, this paper takes into focus the similarities between an aesthetic experience and the transformative experience in psychoanalytic treatment. Because non-representational aspects can only be perceived in enactment, a different type of understanding is required and embraced in “scenic understanding”. Winnicott's “potential space” plays a key role for this kind of enactment and simultaneous containment. However, not just in Winnicott's sense is psychoanalysis a creative activity that rehearses and transforms early object relations. Bollas' sense of the “unthought known”, Bion's sense of the transformation in “O”, and Daniel Stern's sense of the emergence of “now” moments and “forms of vitality” also appropriate aesthetic mental connections within the psychoanalytic session, much as in the reception of modern art. Comparison to Rothko's “Black on Maroon” paintings and their effect of ‘assuming’ the viewer and triggering existential phantasies is a guiding feature in the elaboration of artistic element of the psychoanalytic process.