D.W. Winnicott's distinctive contribution to our understanding of human development, based on extensive clinical work with babies and young children, is known and valued the world over. In Playing and Reality he is concerned with the springs of imaginative living and of cultural experience in every sense, with whatever determines an individual's capacity to live creatively and to find life worth living. The ideas expressed here extend the theme first put forward in his paper 'Transitional Objects and Transitional Phenomena' published in 1953. They relate to an area of experience that has for centuries been a recurrent preoccupation of philosophers and poets. This intermediate area, between internal and external reality, is intensely personal, since its existence depends, as does the use that can be made of it, on each individual's early life experiences. If children can utilize this realm to initiate their relationship with the world, first through transitional objects, and later through play and shared playing, then cultural life and enjoyment of the cultural heritage, will be open to them.