Career decisions are daunting for everyone. But adolescents who live in institutional care are deprived of a conventional family set-up and therefore, face greater difficulty in taking such decisions. In the current education system, adolescents who decide to continue with general education have to select an academic stream after Grade X. This choice has a substantial and irreversible effect on the future career prospects of these adolescents. In the light of these facts, this paper presents a case study of one such adolescent who lives in institutional care. In order to understand the nature of his career decision-making difficulties, the Career Decision-making Difficulties Questionnaire (CDDQ) was administered. As he exhibited indecisiveness, a semi-structured interview was conducted with him to unearth the sources of his indecisiveness. In addition, in-depth interviews were also conducted with his peers and his caregivers along with personal observations to gain a deeper insight into the nature of his career problems. Finally, a personalized strategy to help him overcome his career decision-making difficulties has been suggested.