This article is inspired by my experience of aiming to teach against oppression on my return to an elementary school classroom after completing doctoral studies in education. The tensions that surfaced as I attempted to disrupt oppressive school knowledge in my second and third grade classrooms motivated me to engage in self-study. Locating my work within the context of the Canadian Prairies, I answer the question of how power relations both constrained and opened up possibilities for disrupting oppressive discourses circulating in everyday life at school by offering a power/knowledge analysis of three critical incidents. My analysis traces how power was always at play through competing discourses of Whiteness, femininity, and colour-blindness as I aimed to resist traditional norms around school discipline; work against the privileging of White, male students; and accept the discomfort of talking to my young students about race and racism. By demonstrating how anti-oppressive practices necessitate the disruption of cherished narratives of neutrality and innocence in education, the findings contribute to understandings about what makes anti-oppressive education both difficult and possible. I emphasize the potential within everyday moments at school for disrupting oppressive discourses and highlight the usefulness of self-study as a tool for learning to teach against oppression as a lifelong endeavour.