The purpose of this study is to explore the possible influence of women’s entrepreneurial orientations (EO) on their decision to opt out from organizational careers to self-employment. It examines how women account for these transitions, reasons for opting for self-employment and experiences of self-employment. This research employs the qualitative methodology using semi-structured interviews as the main data collection tool. The study revealed that the entrepreneurial orientations of the women under study are commonly associated with the generally successful entrepreneurial behaviour of risk-taking, creative, proactive, competitive, aggressive and confidence. This suggests that enterprises and their women owners may benefit from efforts to
increase their levels of entrepreneurial orientation in order to survive the dynamic, fast-paced and complex business environment characterized by shorter life cycles, globalization, and continuous improvements in technology. Hence for the women under study with higher entrepreneurial orientation levels, their transitions from their organizational career to self-employment or small business ownership are seen as attractive career moves.