Future orientation refers to an individual’s conscious portrayal of upcoming events, encompassing thoughts, motivations, and emotions. Research on future orientation has primarily focused on adolescents due to their perceived necessity to prepare for adulthood. To investigate the hopes and fears of Italian adolescents in post-pandemic times, as well as age and gender differences and the associations between future orientation, self-efficacy, and perceived academic achievement, a survey was conducted with 388 Italian high school students. The Future Orientation and Life Course Prospective Questionnaires, along with the Problem-Solving Self-Efficacy Scale, were administered. Data analysis involved content analysis of hopes and fears, as well as statistical methods (t-tests, Pearson’s correlation coefficients, and multiple regression analysis) were employed. A greater number of fears than hopes were mentioned. Age differences were marginal. Compared with males, females expressed a greater number of hopes and fears and provided more detailed insights into their fears within the domains of higher education, self, and the general existential category. As expected, positive and modest correlations were observed between future orientation, self-efficacy, and academic achievement. Notably, self-efficacy and work/career future orientation were found to predict academic achievement. The results are discussed in terms of their relevance for school educational programs.