Despite late modernity and risk society discourses about the decreasing influence of structural factors on educational and occupational attainment, it has also been argued that socio-economic background and gender continue to influence individuals' school-work transitions. Comparing youth apprentices and academic high school students in Canada and Germany, I show how working-class students planning on attending university perceive these plans as far more risky and uncertain than do their peers with highly educated parents. Similarly, working-class youth in apprenticeships are confident about their success in these programs. While conditions of late modernity or risk society may have created tendencies toward individualization, young people continue to draw on social experiences rooted in their habitus. But rather than seeing school-work transitions as either structurally determined or largely individualized, I propose that individuals form dispositions based on a reflexive understanding of their position in the social structure. (Contains 3 tables and 3 notes.)