AbstractA growing body of research suggests that contemporary law firms face challenges with the retention of legal talent—especially women and racialized lawyers. Yet, we know little about the conditions that prompt lawyers to leave law firms or where they go after leaving. This article builds on the scholarship of John Hagan, emphasizing the role of social capital in law firm culture, and work by Emmanuel Lazega, tracing dimensions of law firm collegiality—both with implications for lawyers’ careers within and beyond law firms. I draw on data from a twenty-seven-year longitudinal survey of Canadian lawyers. Using piecewise exponential survival models, I examine organizational, cultural, and individual factors that may encourage mobility from law firms. The study reveals a pervasive gender difference that is not explained by human capital, organizational characteristics, or individual traits. Results also demonstrate the importance of social capital and firm culture—specifically, the presence of workplace policies of flexible scheduling, lawyers’ sense of a good match with their firm, their satisfaction with status rewards, and finally, the role of mentors—in shaping the flow of legal talent from law firms to various job destinations.