This is a short, informal discussion paper which examines the concepts behind Lave & Wenger’s (1991) theory of Communities of Practice and Situated Learning and reflects on how these concepts can inform our understanding of professional learning. Through the use of Socratic-type dialogue, the author uses a personal narrative to test some of the assumptions and tacit beliefs which surround situated learning, in order to identify and reflect on some of their limitations when applied in a practical setting.