This article reports a study designed to examine the mediating effect of vice-principals' job satisfaction on the relation between their responsibility roles and career aspirations. Based on a Hong Kong data set, the study confirmed that responsibilities had both a direct effect and an indirect effect on career aspiration; the latter was mediated by job satisfaction. When specific responsibility dimensions were being considered, the two dimensions of "leader and teacher growth and development", and "teaching, learning, and curriculum" were found to have an effect on job satisfaction, which in turn, influenced career aspiration. The dimension of "Resource Management" did not link to job satisfaction, it was however a predictor for career aspiration. Implications of the findings were discussed. (Contains 6 tables and 1 figure.)