Applying path analysis to 237 secondary school students and 320 post-secondary students in Singapore, parents' education was found to have important effects on adolescents' educational aspiration as mediated through educational track and adolescents' financial stress and self-esteem. This effect is strong for adolescents in both secondary and post-secondary education, with slight differences in the specific psychological process. The findings imply calibration of education towards parity and psychosocial interventions to improve adolescents' self-concepts, coping and aspirations. However, in the context of fast economic transformation, a burgeoning middle class, a differentiated education system, and high-income inequality, policy and psychosocial interventions will have limited effectiveness without addressing labour market disparities and the social stigma of vocational and technical education.