Our interest in understanding the determinants of adolescent childbearing and how adolescent childbearing influences educational trajectories derive from a concern about the inverse relationship between educational outcomes and adolescent fertility. Through in-depth interviews with 118 women, we contrast the educational trajectories of adolescent and adult child-bearers in urban neighborhoods in Paraguay and Peru. The findings suggest that adolescents who face obstacles that discourage academic achievement and high aspirations in life are also more likely to bear children. Their expectation of having a life different from their parents is small or nonexistent. Such females lack incentives to prevent pregnancy and may even plan to get pregnant. Moreover, the results of this study do not support the conventional assumption that the problem of school dropouts begins with the pregnancy, but can also result from early formal unions, the low quality of education offered, and generally low expectations of life. The policy responses therefore have to do much more than merely provide information about and access to contraceptives. The paper calls for a series of school-based interventions to provide adolescents with quality sex education, encouragement in setting life goals, and support in remaining in school and returning after childbirth.