The strong emphasis placed on educational achievements as a precondition for successful adult life in Western societies attests to the fact that school plays a significant role in setting the standards for normality and conformity among young people today. The focus of this article is on the subjective orientations to schools and schooling expressed by young people on the margins of school. By adopting a biographical approach to young people’s lives, this study examines how ninth graders make sense of their educational career from a particular transitional vantage point between compulsory and post-compulsory education, and from a marginal position in the current educational context. The article draws on research that focused on the biographies and future hopes of 15- to 17-year-old ninth graders attending either programmes for young people in need of support (‘Pilot’, part of targeted youth work) or an alternative school (‘My Own Career’ classes, part of flexible basic education). The article suggests that for young people on the margins of school, the contribution of compulsory education to the conceptualization of educational pathways in the future is ambivalent, sometimes even disempowering, and the weight of past conflicts with school forces young people to find ways to renegotiate their relationship with education.