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Using the High School Longitudinal Study of 2009, this study examines the differences in various high school outcomes, postsecondary trajectories, and employment outcomes between students who worked and students who did not work using propensity score matching. There were little to no impacts in high school outcomes between the groups. Students who worked in high school saw positive employment outcomes three years after high school in the form of higher rates of full-time employment and higher annual incomes compared to those who did not work. Finally, working too little results in no benefits across any of the outcomes; however, working more hours results in more risk for negative outcomes in high school, but there are better long-term employment outcomes.