Using collaborative autoethnography, critical incidents, and artefacts, one teacher/coach (T/C) role conflict is contextualized in the Canadian physical education & school sport (PESS) setting. The purpose of the project was to use CAE in conjunction with a systematic analysis to promote personal narratives as both an approach to practitioner reflection and as a form of research inquiry to forward the field of PESS and occupational socialization. Data analysis sought to answer the singular question: Was the experience educative? An educative experience required alignment with the Meaningful PE democratic principles of autonomy and inclusivity. Critical accounts of T/C role conflicts resulted in the undesired continuity of T/C role socialization. By sharing these stories to learn by educators are encouraged to reflect on, question, and consider T/C roles in their educational settings.