In this paper, I explore the transitional spaces of teaching and writing by restorying an anomalous event in my teaching of Canadian literature in a grade seven classroom and my efforts to decolonise that teaching. Thinking with Elizabeth Ellsworth's concept of pedagogy as it relates to knowledge in the making and the learning self, I take seriously the manner in which this pedagogy challenges the cultural myth of teacher as expert identified by Deborah Britzman. In my story of de/colonising teaching, a transitional space opens up when I become aware of the ways in which I work against the goals of decolonising in my very efforts towards them, the risks I take, and the damage I can do as I implicate myself and my students in this process. As I teach and as I write, I build from the ruins of this difficult knowledge what it means to de/colonise as an educator.