In Sweden, and in most other OECD countries, post-16 education is a general requirement to succeed in adult life. By the late 2000s, after about two decades of policies for student choice and publically funded free schools, students’ results in PISA had plummeted. A recent reform for stricter demands on schools and students includes strengthened qualifications for entry into post-16 education. This article explores how students maneuver in their choice of upper secondary school study pathway including their ideas on future education and career. Methods used were questionnaires and focus group interviews with students, document analysis and statistics, and snapshots of media comments. The study shows that perceived ‘rational’ student choice is closely related to social interaction, geographic place and time. Influential also are habitus and cultural capital affecting gendered recruitment patterns. The study further indicates lack of knowledge and understanding of the reform among students. A major conclusion is that current Swedish polices may exclude many school students in upper secondary education, and also reduce their opportunities for future life chances, with notable negative implications for collective and economic development.