The study's purpose is to identify the psychological profile of women entrepreneurs, and assess the extent to which their entrepreneurial motivation may be influenced by the territorial and conjunctural contexts in which they operate, and by their capacity to reconcile the demands of family and business. A questionnaire was used to gather data on recent entrepreneurial initiatives by women in Northern Portugal. Structural equation models validated the links between women's dual role (family/business) and their psychological/cognitive profiles, their business start-up propensity and the firms' success. The study suggests that while a correlation exists between motivation and business environment that positively influenced women's start-up decisions and subsequent success, the motives underpinning decisions in rural and urban contexts differ. However, women prove capable of effectively managing their dual role as wife/mother and entrepreneur regardless of territorial context. The paper confirms women's capacity to reconcile the demands of work and family as a key variable, offers tentative conclusions as to how the current economic and financial crisis may influence women's entrepreneurial motivation, and recommends new directions in research that may better inform entrepreneurship theory, practice, policies and teaching.