This article is a collaborative self-study of our development as beginning teacher educators over the course of an academic year. A focus of our self-study was our shared interest in the role of theory and of practice in teacher education programs. Theodore taught a philosophy of education course and Shawn taught a practicum supervision course. Both authors share autobiographical excerpts of their teaching contexts and the problems of practice that they encountered. Our analysis suggests that the dichotomy between theory and practice is unhelpful and unproductive for both teacher candidates and teacher educators. Theory and practice are densely interwoven aspects of teaching that can be tacitly separated by coursework in teacher education. We advocate a pedagogy of teacher education that explores the radical middle between theory and practice.