Although women entrepreneurs are particularly important in developing country and emerging economy contexts, their activities often are culturally constrained. Many of the constraints imposed are gender-based, that is, they are grounded in social norms and values that see women as subordinate to men and frequently result in women’s limited autonomy and lower access to education and other support mechanisms. To understand the cultural constraints that reduce the attractiveness of entrepreneurship as a career for women, we studied the cases of five educated Ethiopian women entrepreneurs. We identified three constraints: (1) ostracism by family and society for becoming an entrepreneur rather than finding a job; (2) objection to the type of business; and (3) censure for prioritizing business over the role of mother. By providing evidence that legitimization of entrepreneurship as a career is a contextualized process, we contribute to work on entrepreneurship generally and women’s entrepreneurship in particular.