Individuals are embedded within systems that possess contextual or ecological developmental assets. Psychosocial assets refer to beliefs that enable positive responses to challenging situations and growth despite adversity, such as hope and a future orientation towards positive attitudes and expectations, as well as persistence and the ability to thrive. Career-related assets refer to career-related resources that characterize career decision-making processes and the world of work, such as the ability to negotiate transitions successfully as well as to tolerate and cope with uncertainty by increasing one’s flexibility and autonomy. This study investigated the effectiveness of two sets of psychoeducational activities in promoting positive attitudes and resources, developmental assets that are useful to strengthen students’ personal resources and shaping their future. This study also highlighted sensitivity to change in personal and career-related developmental assets. Using a mixed design approach, 108 students with an average age of 13.91 years were asked to participate in two psychoeducational activities. The first activity focused on developing a positive future self-identity and the second activity on career exploration and knowledge about the world of work. The results show that each of these two activities support the development of psychological assets as well as of a perspective that addresses complex dynamics and that may reduce inequalities.