This article explores how women in top leader positions navigate between the two contradictory cultures of masculinity and femininity and, in particular, if and how these positionings and negotiations develop over time. Drawing on working-life biographical interviews with women on the top of organizational hierarchies within the crisis management systems in the Nordic countries, the article illustrates women top leaders relating to norms of masculinity and femininity, demonstrating how these have shaped their roles as top leaders, and how these have shifted along their careers. It shows how, in the beginning of their careers, women in organizations marked by cultures of masculinity conform to these gendered norms, while in their roles as top leaders, they do gender differently and assume roles as change agents. The findings suggest that processes of navigation between organizational cultures of masculinity and societal cultures of femininity can be better understood when individual experiences are situated within their gendered social and cultural expectations.