The contribution presents an experience conducted in a secondary school following a careful rereading of the Institute Self-Evaluation Report (RAV) and a long analysis by the teaching staff regarding the frequent difficulties that many students encounter in the final period of studies relating to university, work and life choices. The objective is to develop the students' self-assessment process, the implementation of transversal skills and metacognitive processes. The working group designed and implemented actions aimed at motivational support, orientation, and reorientation of students through interventions aimed at preventing and combating school dropout, job placement and the prevention of educational failure, as reported for orientation Guidelines (D.M. n. 328 del 22 December 2022).