Within the phenomenon of entrepreneurship, the extant literature suggests that the normative actor is embodied by and through stereotypical masculinized characteristics. In this paper, we contextualize entrepreneurship as self‐employment in order to explore how such stereotypical characterizations might influence women's attitudes toward this activity. However, rather than analyzing the confirmatory effects of stereotypes, we critically evaluate the effect of counterstereotypical characterizations upon women's propensity for self‐employment. Drawing upon life‐span data, we explore whether self‐employed mothers disconfirm masculinized stereotypes and so act as positive role models for their daughters. As hypothesized, we found that maternal self‐employment has a counterstereotypical effect and so positively influences daughters to become self‐employed. These data indicate, however, that this effect is tempered by personal stereotypes held by daughters; moreover, it is shaped by significant life events (marriage, parenthood, education, and prior managerial experience). By using a robust data set, this paper contributes to our understanding of how stereotypes and role expectations influence women's propensity toward entrepreneurial activity.