Retaining teachers in the workforce is a major social issue as this vital profession suffers from low levels of prestige and high levels of attrition. This article is a report on research into the psychological predictors of career engagement in preservice and practicing teachers (N = 364). It was hypothesized that teachers’ conscientiousness and neuroticism would predict higher and lower career engagement, respectively, both directly and indirectly via career optimism. Structural equation modeling affirmed that career optimism mediated the relationships of conscientiousness and neuroticism with career engagement. The current findings highlight the need to investigate the contribution of career optimism to teachers’ career engagement to capitalize on adaptive personality processes and mitigate the deleterious effects of negative emotionality.