This study investigated how African American women from low-income, single-parent female-headed households conceptualize work and transitions to work, and how these conceptualizations relate to the dominant discourse of work underlying policies and practices in education-for-work. The study used the construct of cultural models as a conceptual framework that takes into account structural influences while at the same time accommodating individual choice, conflict among beliefs, and contradictions between beliefs and actions. Two generations of African American women who had received public assistance were interviewed about their beliefs and experiences with work, as well as what they learned about work in the context of their families. The cultural models identified through the interviews were grouped into two broad areas concerned with finding work and success on the job. The findings challenge some prevalent assumptions and approaches in work-related education for low-income women.