ABSTRACT Reflection of everyday life in connection to post-socialist transformation inevitably includes a gender perspective. Within this broad framework, the paper concentrates on two aspects of the transition: new professional opportunities on the one hand and persisting gender patterns, which put a burden on women to cope with both work and family care. The paper focuses on the management environment to address the topic; the author reflects on the issue through the analysis and interpretation of the life and professional stories of two Czech women managers. However, it does not offer a mere reflection from the point of view of the “elites.” It convincingly shows how everyday life and the ongoing connection of women with the sphere of family and household functioned as an inhibitor for women to enter top positions, positions in which it is possible to exercise the power to make decisions and influence the functioning of society.