Whereas in years past, young people typically made a discrete transition from school to work, two ideal typical routes now characterize the sharing of school and work roles during adolescence and the transition to adulthood. Longitudinal data from the Youth Development Study show that one route involves less intensive employment during high school, followed by continued part-time employment and postsecondary educational investment. This pathway, more common for youth of higher-class origins, is especially beneficial for young people from lower socioeconomic backgrounds. A second route is early intensive work experience during high school that is less conducive to longer-term educational and wage attainments. (Contains 1 figure and 1 table.)