This work considers women who have left jobs within organizations to set up their own businesses. The project thus explores two worlds: the world of the organization and the world of the small business owner/manager. However, it is not sufficient to limit the scope of the research to these two contexts; equally important are the spaces in‐between. An examination of the transition from employment to self‐employment is crucial in understanding the experience as a whole. Two case studies are used to illustrate how particular women managed the transition. It is then considered how this experience can be conceptualized theoretically, assessing the extent to which existing theories offer adequate frameworks for understanding. Implications for further research and the development of a more relevant conceptual model are addressed.