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A number of oft-cited studies find that more education is correlated with less political violence, hypothesizing that years of schooling proxy for opportunity costs. In other words, when one is educated, there is simply too much to lose to become involved in violence. Youth unemployment is also an increasingly noted security concern with the logic that when youth don’t have jobs, they are easier to motivate into violence. In both sets of arguments, youth themselves are often inadequately consulted about their aspirations. Will any education or any job do? This paper, based on surveys and interviews with Nairobi-based youth that are both in secondary school and those that have dropped out, explores youth’s aspirations and the relationships between aspirations, peace and conflict. It argues that youth have high aspirations for certain types of education and careers, but also for family, quality of life, community service, and status. It argues, moreover, that most of these aspirations will go unmet given the Kenyan opportunity landscape. The paper questions if and how high and positive aspirations themselves may, even if unmet, help youth choose positive paths or whether aspiration gaps present a heightened risk for violence.