In a changing and complex world, young people are expected to make decisions and choices regarding their education and future. The purpose of this paper is to illustrate how guidance counsellors and teachers view their role in supporting students in these choices, and how young people regard the support they receive and have received during their years in school. The empirical data used in this paper is part of a larger study conducted in a municipality in Sweden. Interviews with teachers, guidance counsellors and young adults who live in or grew up in the municipality are presented and analysed in the paper. The empirical data also consists of surveys with students in their ninth year as well as students in their last year at school. The analysis is based on Pierre Bourdieu’s theory of field, capital and habitus. The analysis shows that there are differences in how the professionals and the young people view the support regarding education and the future. Young people feel that they have received little support from the school and want more guidance/help from teachers and guidance counsellors regarding their educational choices and their future. From the professionals’ side, there is an explicit fear of influencing the young and therefore they take a more passive approach. How to understand this fear and its consequences from a gender and class perspective is discussed in the conclusion of the paper.