Vocational education and training (VET) is one of the key interventions targeting youth unemployment in sub-Saharan Africa (SSA). Previous research on occupational sex segregation (OSS) has suggested that men and women exhibit different education attainment and confront discrete work opportunities due to social expectations governing women’s roles within the home and outside of it. This qualitative study used in-depth interviews with twelve women working in the male-dominated technical trades for which they were formally trained to interrogate the barriers to Namibian women’s participation in non-traditional occupations. Specific foci of inquiry were: the influence of gender norms on enrollment decisions and obtaining jobs; and the extent to which motherhood inhibited one’s labor market mobility. The data confirms that norms governing ideas of what is masculine and feminine contribute to the channeling of women into professions perceived broadly to be socially appropriate for them in Namibia. Childbearing and rearing were not significant barriers to study participants’ mobility because extended family members afforded the women the flexibility to work by helping care for their children. A number of the interviewees expressed a preference for working with men, challenging the oft-cited development narrative that women ally themselves with other women and tend to view themselves in opposition to men. By providing context-specific information on some of the factors contributing to occupational segregation in Namibia, this study adds to the existing development and feminist literature related to the interplay between the productive and reproductive spheres of women’s lives as well as their options and choices concerning each.