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This presentation begins by examining several common framings of “progress” and “progressive,” and ways that intentionally anti-oppressive initiatives in schools of education (without both types of framings) can be both contradictory and counterproductive. The purpose of this presentation is to illuminate such paradoxes and explore productive ways to reframe such concepts and initiatives. The analysis draws on Queer Studies, Asian/American Studies, and postcolonial studies as the theoretical frameworks, and engages in queer autobiography, critical family history, and critical policy studies as modes of inquiry. Data include narratives of two key points of intervention in the author’s personal journey through academia in various leadership roles – namely, an intervention regarding leadership, and one regarding activism – alongside the author’s family history of immigration at the intersection of emerging empires on the world stage. Weaving together these personal narratives, the analysis speaks to leadership and activism by asking how a Queer+Asian analytic frame can and does trouble “progressive” approaches to both institutional change (of universities) and policy change (regarding K-12 and higher education); that is, the findings speak to Queer+Asian readings of “progress” that demand a reframing of anti-oppressive leading. The presentation ends with several recent resources and initiatives that strive to address these paradoxes.