This article describes the challenges encountered by a teacher educator and self-study practitioner as he attempted to facilitate a group of colleagues in learning about and engaging in self-study over a two year period. While competent in conducting self-study for himself, the author had never before tried to teach it to others. This led to teaching experiences in which the author grappled with his decision-making across three critical facets of his pedagogy. The findings of this self-study indicate that it is possible to broadly categorize these dilemmas in decision-making as instructional challenges, relational challenges, and methodological challenges. Uncovering and discussing these challenges gives those involved in the self-study of teacher education practices community an opportunity to consider how such dilemmas might be navigated beneficially to advance understanding and use of self-study methodology by others.