While female representation in the top diplomatic circles was almost nonexistent during the Czechoslovak era, the number of female diplomats in the Czech Republic has steadily increased since the fall of the state-socialist regime. Women are currently solidly represented in the Czech Ministry of Foreign Affairs (MFA), but very few (14%) reach highest diplomatic positions. This study examines the main challenges that influence the careers of top diplomats using quantitative and qualitative data, including official statistics and documents of the Czech MFA and interviews with top diplomats and officials. The results indicate that work-family conflicts are the main challenge for all diplomats. However, women are apparently affected more disproportionately because of the existing “double burden” and a specific “concept of motherhood” vested in a deeply essentialist understanding of gender roles. These barriers have origins at the personal, institutional, and state levels that are strongly interrelated and historically and politically path dependent.