This paper presents a self-study project that goes beyond the surface of praxis to examine the internal academic teaching process of a PK-12 school leader educator. The study systematically relates one professor's intrapersonal struggle and professional challenge in addressing his lived contradiction of teaching aspiring school leaders. Results address salient questions that teachers of leaders must pose for themselves about their work--particularly pertaining to the scholarship of teaching and learning. Self-study, a disciplined professional development practice, lends important insights as a research genre into school leadership preparation.