This thesis investigates the gender disparity among female teachers and principals within the Japanese education system. The purpose of the study is to identify factors contributing to this imbalance and to explore the career aspirations of future female educators alongside the experiences of retired female principals. Using a mixed-methods approach, quantitative surveys and qualitative interviews were employed to gather data. The surveys aimed to understand the career aspirations of future female educators, while interviews provided insights into the experiences of retired female principals. The results reveal a complex interplay of societal expectations, institutional structures, and individual aspirations shaping women's professional trajectories in education. Despite the high representation of female teachers, the proportion of female principals remains significantly low. Implications of the study highlight the need for addressing systemic barriers and fostering an environment conducive to the professional development and advancement of women in educational leadership roles. By promoting gender equity and inclusivity, policymakers, educators, and researchers can work towards a more diverse and representative education sector in Japan.