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While studies explore how teachers think about teaching as a profession, the same cannot be said of principals. This qualitative study of 15 principals finds they recognized features of their work that characterize it as professional yet felt challenged to engage these characteristics in their most basic work functions. We identify three frictions experienced by school leaders as they balance their professional identity with their professional obligations: between autonomy and dependence, between psychic costs and psychic rewards, and between proficiency and lack of expertise. With a focus on the unique position that school principals play in schools, this study sheds light on the under-examined concept of professionalism in school leaders.