This dissertation focuses on furthering our understanding of how labor markets work. Each essay sheds light on how individual, governmental, and institutional factors combine to determine economic outcomes within specific labor markets. The first chapter uses the Affordable Care Act's employer mandate to ask if variation in health expenses at the individual level can affect labor market outcomes. Using a difference-in-difference estimation strategy the essay shows that higher cost workers face lower wages and increased unemployment as a result of the employer mandate. Specifically, each dollar of annual medical expenses is associated with a $0.30 to $0.40 wage penalty. The negative changes in labor market outcomes for higher cost workers hi...