Through three chapters of this dissertation, I explore gender differences in self- employment patterns from a sociological perspective, emphasizing their role in the context of gender inequality in the labor market. These studies aim to enhance our understanding of gender disparities in the labor market and how women and men leverage self-employment differently to address work-family conflicts, particularly against the backdrop of increasing job precarity and the limited institutional support. Each of the three papers raises the following research questions: 1) What are the different typologies of self-employment, and how are they associated with one’s socioeconomic background and gender? 2) How do a partner’s longer work hours shape one’s decision to transition to self-employment? 3) Upon parenthood, how do mothers incorporate self-employment into their careers, and how do different labor market contexts of gender disparities and self-employment rates (United States versus South Korea) moderate these patterns? Combined, these projects broaden our under- standing of an underexplored job option when faced with work-family conflicts, and how this option operates differently for women and men.