Play, according to Winnicott, takes place in the potential space between inner and outer worlds. Adult creativity follows on in a direct developmental line from the creativity of the infant (facilitated by the mother or caregiver) through use of the transitional object and the play of the child. Following the artist interviews, and describing aspects of Patricia Townsend’s own process of creating artworks, this chapter considers the artist’s interaction with her medium as a form of serious play. The artist imbues the developing artwork with her own inner experience so that, during the process of its making, it is both an object in the outside world and a part of her inner world. In addition to the writing of Winnicott, the chapter refers to the work of psychoanalysts Robert Caper and Joyce McDougall and to interviews with artists Gina Glover, Sian Bonnell and Jo Volley.