Taking as its starting point Mother Ann Lee’s philosophy that “every force evolves a form,” this paper considers a painting by Philip Guston as a way of exploring how the artist’s process of actively “evolving” his form can help us engage more deeply with unconscious material, and in the process of psychoanalysis itself. The author connects Guston’s particular visual language and the ways he describes having found this language to Freud’s writing on free association and to Winnicott’s facilitating environment. A parallel is drawn between the active search for freedom and “range” in the artistic process and in the therapeutic relationship. Expanding on her earlier concept of the “generative unknown,” the author explores how her “training” as a poet combines with and echoes visions of an intersubjective psychoanalysis to inform how the work of therapy and the therapeutic relationship can “evolve” into their deepest forms.