Understanding the academic and career aspirations of adolescents and their destinations could inform policy makers and educators about how best to provide support at society and school levels to facilitate adolescents transitioning from school to further education and work. The current qualitative study investigates seven senior secondary students from three schools with varying intakes of student ability under the "Secondary School Places Allocation System" in Hong Kong. By employing a Systems Theory Framework, the study looked into the academic and career aspirations of these students and tracked their destinations immediately after secondary school graduation. Findings show that the academic and career aspirations of adolescents and their destinations are shaped by prevailing preferences for attaining higher qualifications, preferably a bachelor's degree, parental and others' influences, and outcomes of public examination results. The implications of enhancing support for the societal, school, and career- and life-planning education of individuals are discussed. Copyright © 2019 Kwok-Tung Tsui et al.