Contemporary youth typically experience considerable floundering and uncertainty in their transition from school to work. This paper examines patterns of schooling and working during adolescence and the transition to adulthood that hasten or delay an important subjective marker of transition to adulthood: acquiring a job that is recognized as a "career." We use Youth Development Study data, obtained from a prospective longitudinal study of 9(th) graders. Estimation of discrete-time logit models shows that adolescent work patterns during high school, as well as the cumulative investments they make in work and schooling in the years following, significantly influence this milestone. Time-varying predictors, including job characteristics and parenthood, also affect the process of movement into "careers".