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In the United States of America (USA), with relatively little institutional support for young people as they complete their formal educations and embark on their careers, part-time employment during the high school years has become an integral part of the transition from school to work. This chapter examines three outcomes of adolescent work investment: education attainment; postsecondary work experience; and family outcomes. Data is used from the Youth Development Study (YDS) which was initially designed to assess the consequences of early work experience. Findings from this study suggest that young people manifest quite different patterns of initiation to work and the pattern of employment in adolescence matters for key markers of transition to adulthood.