Numerous studies document women’s overrepresentation among those leaving the profession of law. Although research has documented high turnover among women lawyers, particularly from private practice, only a handful of studies have explored the factors precipitating the decision to leave. The main causal factors identified to date include difficulties associated with combining family life and law practice and problems of discrimination and blocked career advancement. In this paper, we analyze data from a longitudinal study of nearly 1,600 Canadian lawyers, surveyed across a twenty-year period. Using survival models to estimate the timing of transitions out of private practice, we examine factors precipitating exits from private practice. We find that women are leaving private practice at higher rates than men. These departures appear to be largely the consequence of organizational structures and a practice culture that remain resistant to flexible schedules, time gaps between jobs, and parental and other leaves. Yet, the careers of contemporary lawyers appear to be characterized by more job changes, discontinuity, and movement between sectors of practice than is commonly assumed. Our paper moves discussion beyond the work-family debate and motherhood, to examine the broader issues of institutional constraints on careers of both men and women in law and policy initiatives to encourage retention of legal talent in private practice.