This exploratory study examines patterns of entrepreneurial engagement across the life course using Group-Based Trajectory Modeling and panel data from the National Longitudinal Survey of Youth 1979. We identify four distinct career trajectories—never, early-adulthood, mid-adulthood, and career-persistent entrepreneurship—and analyze differences in their timing, duration, and frequency. We then explore how early-life family capital is associated with trajectory membership and how these paths relate to psychological and financial outcomes in middle adulthood. Instead of focusing on single points of entry or exit, this study traces the full arc of entrepreneurial careers—revealing how they unfold, develop, and diverge over the course of individuals’ working lives.