Students in Finland are obliged to apply for upper secondary education during their 9th year. The main divisions occur between general (academically oriented) and vocational upper secondary education, and within vocational education between female and male dominated sectors. In this article we discuss the tension between these options and explore young people's hopes, choices, and transitions. These are related to expectations imbedded in policies and practices. We present a contextualized and cross-cultural analysis in which interviews and ethnographic data from different settings are used. We suggest that there is a taken-for-granted backdrop to students' choices that includes norms and expectations concerning social class, gender, sexuality, and/or ethnicity. We suggest, moreover, that the analysis of educational choices ought to be situated within the larger context of the marketization of the politics of education. (Contains 2 tables and 11 footnotes.)