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Voter turnout in the United States is lower than most other advanced democracies and is largely driven by social factors, including education. This paper takes a life course perspective to examine how educational opportunities during adolescence may shape one’s political identity and voting across the life course. In particular, I investigate the role of empowering experiences, including leadership positions and advanced course-taking, and disempowering experiences, including school discipline, in shaping voting outcomes in midlife. Using a nationally representative sample of high school students linked to their voting records, I find that adolescent (dis)empowering experiences are predictive of whether and how often individuals vote in midlife. I consider the roles of family and civic background, school habits and skills, educational attainment and voting in early adulthood in the process. My findings suggest that advanced courses in high school may place adolescents on more politically engaged pathways into adulthood and positively predict midlife voting. In addition, having disciplinary problems in school can place students on pathways towards political disengagement, and negatively predicts voting in midlife. These findings persist when considering both selection into these experiences and education and voting in early adulthood. This paper provides evidence that adolescence is a critical period for the development of a political identity and that (dis)empowering experiences in high school play an important role in the process of developing an engaged citizenry.