This study, conducted in France, sought to describe the organization of the content of the social representations that high school students in transition construct of work and their own future, taking into account two variables: their type of secondary school and the anticipated length of their post-secondary education. For this purpose, 669 adolescents enrolled at three types of secondary schools (middle school, general high school, and vocational high school) were given two free-association tasks (with the inducers "work" and "your future"). Prototypical analyses for each of the variables considered were carried out on the corpus of words collected. The results highlight the place occupied by money and post-secondary education in the set of representations and the advantage of taking into account the subjective variable "anticipated length of post-secondary education" to better understand the role that contemporary uncertainties play. Thus, students who do not plan to pursue higher studies seem more worried about their future than others. On the theoretical level, the article notably highlights the benefit of integrating certain concepts developed in social psychology along with studies developed in the field of career guidance. In terms of practice, finally, it argues for a better integration of anticipations in the support aimed at helping students plan their transitions.