In the EU, young people planning their pathways through education and into the labour market are faced with multiple choices and possibilities but also a number of risks and uncertainties. The expansion of education has increased educational opportunities and participation, while the rising educational level of the population has caused an inflation of the relative value of educational degrees and strengthened the link between educational qualifications and occupational positions. School-to-work transitions have become more difficult, and for many young people, there is a contradiction between the rhetoric about good education leading to secure and attractive careers and the perceived reality in their social surroundings. The paper aims to examine how young people themselves, especially those from more disadvantaged backgrounds, see their future educational and occupational trajectories. The focus is on the different social and system-level factors affecting the amount of concern adolescent have about their future. The survey data (N = 628) was collected from Finnish ninth graders in three large cities in 2010. Together with more basic statistical methods, structural equation modelling is applied in the analysis. The results will be discussed in the framework of the prevailing neoliberal discourses of competition and choice.