Women around the world continue to encounter persistent and systemic gender bias, harassment, and discrimination, navigating what Eagly and Carli (2007) describe as a "labyrinth of inequality" as they strive to achieve their full potential within organizations and society. Despite decades of research evidencing and describing the barriers women face, there remains a paucity of longitudinal, qualitative studies exploring the lived career experiences of women who successfully charted a pathway through the labyrinth and progressed to senior career levels, particularly in male-dominated fields like IT. Contextualized in feminist theory and gender power dynamics, and drawing on coping, resiliency, and narrative inquiry theories this study investigates how 28 women holding senior career roles at some of the world’s largest IT companies retrospectively and in real-time frame, understand, and make sense of their personal journeys navigating gender-based challenges over time. This study introduces the concept of learned resilience to describe and explain the temporal, cognitive, and psychological process through which women can chart a pathway through the labyrinth and reclaim their voice, agency, and power.