Creativity involves both dialogue and medium, although the specific dialogue and medium in analysis and in the artist's creations may differ. For the artist, there is a dialogue in her mind, between herself and the process of creating a work of art, as well as an ultimate dialogue between herself and the viewer. The analyst, on the other hand, does not aim at creating a new vision, but at creatively altering an already formed, existing vision in the patient's psyche. The analysis, then, involves affective dialogues within and between participants, altering and co-creating patterns in their minds. In both instances – art and psychoanalysis alike – multiple bidirectional dialogues lead to matching patterns of recognition and transformation of the internal and external experiences. Using vignettes from clinical practice with patients, as well as from artists' work, this paper describes the conditions, processes, goals, and effects of the creative endeavors in both therapeutic and aesthetic pursuits.