This paper reports an investigation of the challenges a former classroom teacher encountered when compelled by experiences as a supervisor of student teachers to forge a distinct pedagogy of teacher education. A qualitative self-study methodology was used to identify and examine the competing tensions that surfaced as the author made the transition from classroom teacher to teacher educator. Unanticipated challenges included establishing his professional identity as a teacher educator, navigating the ambiguous role of teacher educator as both advocate and evaluator, and dealing with external sources of resistance manifest in the belief systems of student teachers and the norms of the public school system.