This dissertation consists of three essays in labor and development economics. The first essay, “Bumpy Rides: School to Work Transitions in South Africa,” quantifies the importance of the option to re-enroll in the school to work transition of South African youth. I estimate a structural model of schooling choice using a panel dataset that contains the entire schooling and labor market histories of sampled youth. Estimates of the model’s parameters confirm the hypothesis that enrollment choices reflect dynamic updating of the relative returns to schooling versus labor market participation. In a policy simulation under which re-enrollment prior to high school completion is completely restricted, the proportion completing 12 years of schoolin...