In a changing and complex world, young people are expected to make decisions and choices regarding their education and future careers. At the same time, there is a continuous increase in mental health problems, such as stress symptoms, among young people in the Nordic countries. One source of stress concerns young people’s outlook on life in general, and more specifically their choice of education and career. This paper is based on a research project in a Swedish municipality with a low level of education. The overall aim of the project was to explore and understand the low education among the citizens in the municipality. The aim of this paper is to illustrate how career counsellors and teachers view their role in supporting students when it comes to these choices, and how young people view the support they receive and have received during their years at compulsory and upper secondary school. The empirical material consists of surveys and interview studies with young people, teachers and career counsellors. The analyses of the results are based on Pierre Bourdieu’s theory of field, capital and habitus with a gender perspective from Beverley Skeggs’ theory on gender and capital. The study takes young people’s perspectives of their education and careers as its starting point. It also examines the support they have received from career counsellors and teachers at compulsory and upper secondary school and also from their parents and other significant persons in their home environment. The analyses show that there are differences in how professionals and young people view study and career guidance. Young people often express a feeling of uncertainty when it comes to their future choices and request more guidance from adults regarding possible opportunities. Several students find it stressful to manage their career choices, particularly if their parents do not have sufficient knowledge to support them in such matters. Girls express a feeling of stress in relation to educational choices more often than boys. Teachers and career counsellors describe a lack of strategies when it comes to vocational guidance and how to address issues of education and future work within the current curriculum. They also express a fear of influencing young people and therefore take a more passive approach in these matters. In conclusion, the results show that there is a gap between young people’s requests for guidance from adults at school and teachers’ and career counsellors’ view of their role in these matters. The results highlights the importance of developing strategies for working with educational and career choices at compulsory school as one way of preventing mental health problems among young people.