This research text is a self-study into my development as a critical pedagogue. In it, I seek to investigate two research questions: (1) how do tensions in my teaching illustrate the systemic challenges of race and gender, which I face on a day-to-day basis, as I work towards a more socially-just teaching practice; and (2) how does the analysis of racial and gender-based teaching tensions help guide my growth toward a more socially-just professional practice? My evolving understanding of my social position in relation to systems of oppression and its effect on my teaching are central to this study. Through this self-study, I have come to discover that when considering power, responsibilities, space, and lived-experiences, the point is to not only acknowledge oppressive systems and one’s place in supporting those, but to go beyond one’s current positioning. Change must be created first (and extensively) within one’s self (as was demonstrated in this self-study), and only then within society. If action does not flow from ongoing, critically enlightened acknowledgement of power symmetries, then the impact of any actions will uphold and preserve systems of injustice. As stated in my data, “I think that’s the whole point about social justice is you never—you never really get there”; it’s a constant process of discovering and learning about one’s own positioning and sitting in that discomfort.