The chapters presented in this dissertation deal with two labor market issues in the United States: (1) the impact of the cost of health insurance on households’ choice of employment sector and (2) job attachment patterns of men and women. Chapter 1 presents the motivation for the research. Chapter 2 models the effect of employer-provided health insurance on households’ decision concerning whether to select into the wage-salary sector or the selfemployment sector. Chapter 3 provides an empirical test of this issue. Chapter 4 provides empirical support for a possible theory explaining why women might exhibit stronger attachment to their job relative to men, early in their careers. Chapter 5 presents the major conclusions of the dissertation and suggests directions for future research.