All too often art teachers in schools find that their art practice falls away as the demands of teaching take over from their own creative practice. But is this separation inevitable? In this chapter I examine the ways in which, what I call, the ‘teaching artist’ might prevent this disjunction by crossing the borders between art and art education. What I propose here is a hybrid field in which the hierarchical distinctions, for example between teacher and learner, word and image, are questioned and the voices of students legitimised.