Most people would agree with the maxim that "success breeds success." However, this is not the whole story. The current study investigated the additional impact of psychosocial factors (i.e., performance obstacles and facilitators) as well as psychological well-being (i.e., burnout and engagement) on success (i.e., academic performance). More specifically, our purpose was to show that, instead of directly affecting future performance, obstacles and facilitators exert an indirect effect via well-being. A total of 527 university students comprised the sample and filled out a questionnaire. We obtained their previous and future academic performance Grade Point Average (GPA) from the university's records. Structural equations modeling showed that the best predictor of future performance was the students' previous performance. As expected, study engagement mediated the relationship between performance obstacles and facilitators on the one hand, and future performance on the other. Contrary to expectations, burnout did not predict future performance, although, it is significantly associated with the presence of obstacles and the absence of facilitators. Our results illustrate that, although "success breeds success" (i.e., the best predictor of future performance is past performance), positive psychological states like study engagement are also important in explaining future performance, at least more so than negative states like study burnout.