The aim of this study is to analyze subjective processes that occur in adolescents starting secondary school that have participated in the “Beginning Secondary School” program, carried out in three public schools under the direction of the GCBA Ministry of Education. The program focuses on providing support during this transition, encouraging reflection on what getting an education means and helping students construct their educational trajectory. Activities included three workshops with each class group coordinated by guidance psychologists, one at the beginning, one in the middle, and one at the end of 2010. The results allowed us to recognize students’ representations, expectations and fears, such as whether the relationship with teachers would be difficult and how intense was the fear of failure. Most students expressed satisfaction with the orientation, which gave them an opportunity to think about their strengths, the obstacles they faced, and possible strategies to construct for overcoming them.