Abstract This study conducts an in‐depth analysis of Japanese women entrepreneurs' career formation, examining how they navigate the acquisition of essential capital, such as human, cultural, social, and financial, to initiate and sustain their business ventures. It delves into the societal and cultural barriers in Japan, drawing comparisons with South Korea to shed light on the factors contributing to the relatively low engagement of Japanese women in entrepreneurship. Interviews were conducted with 69 women entrepreneurs, unveiling diverse career trajectories and underscoring the significant impact of life events on their decision to pursue entrepreneurship. This study covers the numerous challenges these women face, from societal expectations to balancing family and work, and it considers how they creatively overcome them. The findings of this study not only highlight the resilience and resourcefulness of Japanese women entrepreneurs but also indicate the implications for policy and practice to foster a more supportive environment for women's entrepreneurial endeavors in Japan and similar contexts.