Human capital attainment at the extensive or intensive margin has large and long-term consequences for individuals. Oftentimes these decisions and preferences are made or formed during youth and young adulthood. In this dissertation, I study three factors that have potential to influence adolescents' education and career decisions. In the first chapter, I track individuals from high school through college to the workforce using Texas administrative data to determine the effects of local labor markets on selection into teaching. I find that local labor market conditions are countercyclical with selection into teaching. I also show that these local labor market conditions have the largest influence when experienced during high school. On average, individuals who sort into teaching because of poor local labor market conditions are of higher ability (standardized tests) and have higher value-added. Further, poor local labor market conditions drive individuals toward certification in at least one shortage area (bilingual/ESL) and weakly away from general elementary studies. The results are consistent with updated beliefs over employment probabilities or changes to risk preferences such that teaching is perceived as a relatively more stable career path. The findings suggest that local labor market fluctuations shape career decisions well before participation in the labor market, and that increasing the relative economic standing of teaching as a career has the potential to improve the future supply of teachers. In the second chapter, I estimate the impact of a Louisiana state policy that mandated FAFSA applications as a high school graduation requirement. I find significant increases in FAFSA completion rates (19 percentage points), and my estimates imply an increase of 1-2 percentage points in college enrollment. There is suggestive evidence that these effects were more concentrated among lower-income students/schools and merit-based state financial aid applications also increased. The design of this mandate implies that pushing students into action may be more effective than informational nudges and that localized support systems such as counselors are important for the success of a top-down policy. In the third chapter, I study the effects of birth control and abortion access on educational attainment and college major choice. Using the rollout of early access to birth control laws across states and time, previous work has suggested that birth control increases educational attainment and entry into professional occupations for women, likely due to the ability to delay childbirth and marriage (Goldin and Katz, 2002; Hock et al., 2007; Bailey et al., 2012). I revisit this work using newly defined legal coding and heterogeneous robust estimators to determine whether reproductive control has an effect on educational outcomes for women. With American Community Survey data, I find the effect of early access to birth control on college completion is not robust to the use of event studies or heterogeneous robust estimators in contrast with other TWFE methods. I also do not find sufficient evidence early access to birth control affects the propensity to select male-dominated college majors. Finally, there are significant pre-trends in abortion laws that question the use of their rollout across states and time in differences-in-differences specifications.