The fields of gender and educational leadership have been enriched recently by analyses of national case studies from non-western contexts. By contextualising women's career development, these studies highlight the importance of including experiences other than those generated from Anglo-American-Australian contexts, thus broadening our knowledge base for more nuanced theorisation in the field. This paper contributes a close examination of the career histories of eight female primary school principals in Hong Kong. Our analyses identify a range of facilitators, including the expansion of promotion opportunities, strong values placed on education and training, professional encouragement and support and help in relieving family responsibilities. Valuable these factors may be, but we argue that they are incidental, informal, familial and individual, and incur the costs of burn-out and guilt. The discussion not only underlines the significance of case study and cultural and contextual specificities, it also provides a nuanced understanding of Chinese patriarchy.