The transition from high school to university is a topical issue in France. This paper focuses on the meaning of entering university for freshmen students after high school in the French context. Our research is particularly centred on the representations that high school students have regarding the university. Furthermore, we studied how the representations changed during the first year. For this paper, we based our work on developmental approach and also on theories which come from the psychosocial field. We decided to emphasize our analysis on the experience lived by these teenagers/young adults. Based on our results, we identified an ambivalence in the meaning of higher education for students. An ambivalence is also sometimes found in counselling between research and practice. Thus, on this political, practical and theoretical subject, we wonder how to put the student at the centre for an effective career guidance.