This article reports the development and psychometric requisites of Visions About Future (VAF), a measure to assess optimism, pessimism, and hope in early adolescence. Two different studies involving Italian middle school students were conducted. With the first study, the items were developed and the factor structure verified by using item analysis, exploratory factor analysis (EFA), and confirmatory factor analysis (CFA); further, convergent and concurrent validity by testing hypothesised relationships with existing measures, were assessed. In the second study, we provided measurement invariance across gender among middle school students. Results provide strong psychometric support for VAF as a valid measure to explore propensity to optimism, pessimism and hope in early adolescence and for career education and career counselling activities.