Background: Within more than 1,600 preK–12 member schools in the National Association of Independent Schools (NAIS) in the United States, there were only seven Asian American women heads of schools in 2019, representing 6% of all heads of color, 1% of all women heads, and 0.4% of all heads of schools. There has been limited research on intersectionality in educational leadership, particularly in the context of independent schools. Purpose of Study: This article sets out to address the research gap in current literature as it pertains to examining the intersectional impact of race, gender, culture, and epistemology on the leadership experiences of Asian American women heads of independent schools, and to deconstruct mainstream leadership narratives by unearthing and complicating critical narratives of a small group of educational leaders who are women of color. Research Design: This qualitative study employs intersectionality theory as the conceptual framework, culturally responsive school leadership as the leadership framework, and elements of portraiture, critical Indigenous studies, and critical race theory as the research methodologies and analytical tools. Data Collection and Analysis: A background information survey was emailed to all seven Asian American women heads of schools to collect contextual and demographic information. The goal of the survey was to find commonalities among the heads and their schools so that a portrait of these seven individuals and their schools could be drawn as an intelligible whole before delineating specific experiences of the research participants. Perceptual information was collected via interviews. The interview protocols were designed to gather information around participants’ pathways to leadership, and their epistemological foundation and its impact on their leadership journeys and styles. Elements of portraiture were used to analyze participants’ experiences based on interviews in this qualitative study. Findings: This study connects culture and epistemologies to leadership practices and shines a light on how these Asian American women heads of schools—despite experiencing stereotype threats, microaggressions, and oppositions—negotiate between the transactional nature of independent schools and the transformational power of educational leadership, and make powerful contributions toward reimagining schools as places with radical possibilities. Conclusions: Asian Americans are a historically disadvantaged racial minority group, and Asian American women in education and academia have faced a long history of discrimination grounded in racism, xenophobia, and misogyny. The NAIS leadership team should better understand what challenges Asian American women face on their pathways to leadership and develop a better support system for all women of color aspiring leaders.