This study examines the effects of role-overload (RO) and self-esteem (SE) on career satisfaction (CS) through work engagement (WE) and job satisfaction (JS). It follows the social cognitive career theory (SCCT) and job demands-resources (JD-R) model. A quantitative survey was conducted on Indian school teachers (n = 630). A serial mediation model was developed to examine the proposed relationship. Hypotheses were tested by SEM and bootstrapping to verify the direct/indirect effects. The results reveal that SE, directly and indirectly, influence CS. The serial mediation was found between RO on CS through SE, WE, and JS. WE and JS also serially mediated between SE and CS. However, RO does not affect CS directly but through serial mediation. Study proposes a structural model with organizational and individual factors influencing CS. Unlike previous researchers, this study combines personal resources and organizational demands predicting CS. The study helps to understand the connecting link between SCCT and JD-R theory. Organizations can make use of this model for developing CS by managing RO through interventions.