This study investigated the vocational aspirations and expectations of 160 African American adolescent mothers living in urban poverty. Discriminant function analysis was used in an attempt to distinguish between participants with, and those without, a discrepancy between their vocational aspirations and expectations. The two groups were found to be distinct in several ways. Depressive and anxious symptoms along with childcare provided by relatives, were associated with a gap between aspirations and expectations. Higher grade point averages, living with biological parents, and having a career mentor were more often associated with a match between expectations and aspirations. A combination of factors, including psychological functioning, social support, achievement, and contextual factors specific to the tasks of teen parenting, should be considered in future attempts to understand and describe adolescent mothers' vocational development.