Increasingly, graduates are taking much more time in the transition from school to work. Recent research suggests that the ability to adjust quickly plays a key role in the transition process. This is even more important today given the tough labor market realities such as exacerbated unemployment levels and global competitions for the few available job openings. Yet new graduates often lack experience and certain skills that employers look for. Those unable to maneuver through the School-To-Work Transition (STWT) quickly may experience further challenges in their career development process. Using a sample of 516 students in their final semester of their university studies in Ugandan and Kenya, the present study examines the role of psychological resources, namely psychological capital and the mechanisms (i.e. Career Engagement-CE, Perceived Employability-PE) through which it works to affect students' readiness for STWT as well as positively evaluating their career success. The major findings of the study reveal substantial positive direct effects of psychological capital on perceived employability, readiness for STWT, and career satisfaction. The double mediation results show that psychological capital indirectly affects the readiness for STWT via career engagement and internal PE, while psychological capital indirectly affects career satisfaction via career engagement and external PE. The implications of these results are discussed.