Underpaid and overworked, preschool teachers face multiple barriers in pursuing higher education. In the present study, we explored how logistical and financial barriers hinder early childhood education teachers and teacher's aides from taking college courses, as well as how academic self-concept and social support influence current enrollment. Telephone interviews were conducted with 68 teachers and 38 teacher's aides currently employed by 85 child care centers in western Massachusetts. Results revealed that both structural and psychological factors are associated with teachers' and teacher's aides' enrollment in college. Financial and practical concerns, however, did not depress current enrollment once other factors were taken into account. Beliefs about education and motivation were critical for enrollment. Social support from parents may indirectly influence teachers' enrollment by increasing their motivation for college attendance. Younger teachers, African Americans, and those with friends in college were more likely to pursue college than any of the other groups. Colleges could encourage the attendance of motivated low-income workers by providing free child care and programs to promote social support by family members and friends.