This paper considers the role of imagination in the context of Bionian Field Theory. Expanding on Hanna Segal’s idea of “what if” dimensions of the analytic process, it is argued that “what if” states engage evocative and vital aspects of objects. They set up particular tensions in the analytic field that trigger “imaginative work.” The processes at work share many similarities with the artist’s creative process. For this reason, William Kentridge’s reflections on his own creative process are used to elucidate “imaginative work” as an esthetic, creative and agentive process. Three case fragments are used to illustrate some of these ideas in the clinical setting.