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This proposal explores the implications of whiteness and white fragility on social justice endeavors in education. In particular, I apply a critical whiteness lens to examine the ways my own positionality as a white teacher educator hindered my ability to critically frame and facilitate meaningful conversations around race and racial privilege in a yearlong professional development experience with novice teachers. I employ self-study methodology as a reflexive tool to center the contradictions of my positionality as a white researcher committed to social justice education who inadvertently failed to engage teachers in meaningful conversations around race and racial privileges.