In this article, the authors examined factors that facilitate or hinder teachers’ and teacher’s aides’ pursuit of college education. Results revealed that both structural and psychological factors are associated with teachers’ and teacher’s aides’ enrollment in college. However, the authors found that the only practical obstacles were related to enrollment were full-time employment and lack of child care for mothers of children under 14. They also found that beliefs about education and motivation were critical for enrollment as well as social support from parents. The authors suggests that colleges and universities that serve low-income working women could develop child care options for them while they are attending class.