Risk Intelligence as a Resource in Career Transition: The Role of College Satisfaction on the Visions about Future Jobs

University transition is a critical step in career construction due to the uncertainty and unpredictability of socioeconomic conditions; these conditions compel people to manage a greater quantity of perceived risks associated with their career projects than in the past, and to face unexpected situations that could compromise their quality of life in educational and work contexts. After all, experiencing well-being during the university path can undoubtedly affect the visions of one’s future work, especially when a transition period is nearby. The present study aimed to explore the role of subjective risk intelligence in expectations about future work, analyzing the potential mediational role of academic satisfaction in this relationship. (2) Methods: A longitudinal study was carried out on 352 Italian university students at the end of the degree course. We used the following measures: in T1, Subjective risk intelligence scale, College Satisfaction scale; in T2, three items assessing the expectations about future work. (3) Results: The main findings showed that subjective risk intelligence has both direct and indirect effects (through the mediation of college satisfaction) on the expectations about future work. (4) Conclusions: The ability to manage risks, also through the contribution of domain-specific satisfaction, can lead to positive expectations toward one’s future work. This could increase the likelihood to perform career-related behaviors in a more proactive way if people have high risk management skills and high levels of academic satisfaction with their university path during transition. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.