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I describe an unusual approach to hone psychotherapy skills and enhance my understanding of complex psychological concepts. Using a few selected artworks, I discuss and illustrate how I used painting and the artworks themselves to enhance learning, explore theoretical confusions and express personal conflicts. I demonstrate how painting and the artworks themselves can enliven memory, illustrate the transference relationship, explore dreams and express deep anxieties experienced during a training psychoanalysis. I link the psychotherapist attuning to the transference in order to make interpretations, to the artist responding to the unexpected artwork emerging on the canvas.