Self-study presents one approach to research that can be used to understand how current teacher educators and teacher education doctoral students (re)develop their practice and are socialized into academic norms. In some of these instances, faculty advisors may serve in a critical friendship capacity. This introduces an important power dynamic into the self-study process as advisors serve in a supervisory capacity over their students. The purpose of the current study was to understand the process through which a self-study-informed critical friendship influenced the development of our relationship as doctoral supervisor (Kevin) and doctoral student (Tori). Data came from each of our reflective journals as well as formal and informal critical friend discussions. Through qualitative data analysis, we sought to identify turning points through a collaborative process. Results indicated that engaging in a critical friendship through self-study provided us with the space and encouragement to critique traditional power structures and develop a more honest relationship. We specifically identified three turning points relative to the development of our mentoring relationship: (a) initial apprehensions and shared frustrations at the beginning of the process, (b) learning about and coming to trust one another through critical friendship, and (c) creating a more enjoyable and effective supervisory relationship. These results highlight both the benefits and challenges of faculty advisors serving as critical friends for their doctoral students and are discussed in relation to occupational socialization theory.