Do adolescents with insomnia really do worse in school? Do people with insomnia earn less? This thesis explores the relationship between adolescent insomnia and human capital accumulation, as well as the relationship between sleep trouble and labor market outcomes, with careful attention to difficult-to-measure confounders associated with insomnia and the outcomes under study. This paper uses The National Longitudinal Study of Adolescent Health (Add Health) to investigate the link between insomnia and economic outcomes while conditioning on potential confounding variables such as demographic characteristics, parents' socioeconomic background, other health conditions, and time-invariant school- and individual- level heterogeneity. In this thesis, I examine short-run academic performance and school functioning (GPA, homework completion, and attention in class) as well as long-run educational attainment (years of schooling completed, high school dropout, and college attendance) and labor market outcomes (labor force participation and personal earnings). Ordinary least squares estimates show that insomnia is not significantly associated with short-run academic performance, but it does correlate with poorer school functioning. This study finds little evidence that insomnia affects employment in young adulthood, but for females, insomnia is negatively associated with annual earnings in young adulthood.