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This paper explores challenges women leaders encounter in independent schools in Canada as they pursue the ultimate role of principal, amid structural barriers in professional and personal life, and the strategies women use to mitigate these challenges. Theories of gender, identity, career, and social justice leadership form the conceptual framework. Data is drawn from a qualitative study involving 14 female educational leaders from 2018. Findings indicate participants experienced second-generation gender bias, limiting their advancement, and that social expectations played a significant role in participants’ career trajectories. This is problematized using a critical lens in the discussion, contributing to a broadening theoretical understanding of obstacles faced by women leaders in independent schools and recommendations for supporting their career climb.