Henry James's novella The Figure in the Carpet (1896) offers an ironic commentary on the failure of the literary critic or reader to fully establish the writer's intentions. Drawing on Winnicott's early interest in the work of James as well as Laplanche's theory of the enigmatic signifier, I consider what James's tale might have to tell us about reading as the cultural site of encounter with the message of the writer. After discussing how literature both provokes and inspires the reader, I extend my field of inquiry to that class of literature we call psychoanalytic theory, reflecting on the unfavourable reception of Winnicott's (1952) paper 'Anxiety associated with insecurity'. I suggest that both Winnicott and James share an interest in the notion of 'creative reading' and that reading can be understood as a place of being alone in the presence of the writer. I conclude by considering some parallels between the figure of the literary critic and the psychoanalyst, offering some brief thoughts about the implications for creativity.