Abstract Decentralisation and deregulation in Swedish secondary education has put more responsibility on local school organization to manoeuvre in a competitive educational context. Political claims foregoing this form of quasimarket development in education stress enhanced opportunities for choices and stimulation of pluralistic interests among students inside a more autonomous school organization. In this paper the issue of educational opportunities is underlined by discussing initial results from an ongoing fieldwork at a Swedish secondary school. Shaped as a case study, the purpose is to investigate how students at both academic and vocational study programmes view their future opportunities in a wider socioeconomic context. More specifically the purpose is to examine how sociocultural conditions become decisive for evaluating possibilities and restraints of schooling. The methodological approach uses multiple qualitative methods, and is inspired by theoretical perspectives that underline the interconnection between individual, organization and society. Emphasis is in particular put on how individual choices are shaped, mediated and channelled by institutional conditions. A theoretical elaboration will be tested by using Pierre Bourdieu’s concept of Habitus, as socially embodied structures, that can be viewed upon as a mediating link between individual action and external power relations of the society. Preliminary results indicate that educational objectives set by the school in question are interpreted rather differently by the vocational and academic students. Individual perception of opportunities coincides with norms and values in the local cultural environment, and results in individual strategies that overlap with local collective beliefs. Both academic and vocational students pursue instrumental goals of material security and social establishment. However, the difference tends to lie in collectively tied practices of pursuing and defining those aims. At the academic oriented programmes school objectives are commonly agreed upon, and are incorporated in the cultural environment. Conversely, mistrust and disagreement towards the goals of the vocational programme seems to prevail among the students. Organisational strategies are shifting in accordance to these different goals, respectively. From supportive and dialog-oriented conduct at the academic track, to conflict filled and disciplining relations at the vocational programme. These early results indicate that students need to take an active part in the specific cultural setting with explicit notions of consistency in order to allocate organizational resources to their favour. Moreover, this case study demonstrate the increasing strong tendency that education is becoming a kind of quasi-market, which presupposes well-informed and ambitious students who seeks to utilise the gains in schooling. Hence, this illuminates the importance of further examination of how sociocultural structures condition students’ practical understanding of the possibilities and limitations of education.