Transformational learning is a process resulting in deep and significant change in habitual patterns of identity, thought, emotion, and action, enabling new approaches to role enactment. This article explores how moving from a framework of dilemmas, which require solutions and one-sided choices, to a framework of paradoxes that embraces tensions and contradictions can contribute to meaningful transformational learning in the context of women's leadership development. Drawing on recent theories of paradoxes and on critical feminist theory, we propose a critical feminist pedagogy of paradoxes for developing women's leadership of social change enterprises. This perspective is put forth based on our analysis of an experiential course in a graduate gender studies program wherein participants take on leadership roles and interrogate them, by integrating theoretical discussions, reflection, and practical engagement in social activism. We use case studies from our