A range of reasons is cited to explain gender differences in business performance in Africa. Within those, the sector of operations is consistently identified as a major issue. This paper uses a mixed methods approach to assess how women entrepreneurs in Uganda start (and strive) operating firms in male-dominated sectors, and what hinders other women from doing so. The study finds that women who cross over into male-dominated sectors make as much as men, and three times more than women who stay in female-dominated sectors. The paper examines a set of factors to explain the differences in sector choices, and finds that there is a problem of information about opportunities in male-dominated industries. The analysis also concludes that psychosocial factors, particularly the influence of male role models and exposure to the sector from family and friends, are critical in helping women circumvent or overcome the norms that undergird occupational segregation.