Hundreds of millions of adolescents across Africa face challenges in many areas of their lives, including elevated risk of HIV exposure and acquisition. Understanding the aspirations and self-perceptions of adolescents could play an important role in better targeting effective investments to break the cycle of adversity for adolescents and into their adulthood. Aiming to understand what adolescents value most for themselves and their future, we analysed and summarised cross-sectional data on the aspirations and self-perceptions of 1519 adolescents living in South Africa, overall and by HIV status. Outcomes were coded from participant responses to two open-ended questions: 'What job do you want to do when you grow up?' and 'What are you most proud of about yourself?'. Associations with HIV status were then evaluated using multivariable logistic regression adjusting for six sociodemographic factors measured from the same cohort. The sample had a mean age of 14 years, 55% were female, and 70% were living with HIV. The five most common job aspirations were: 'Health and Medical Science Professionals' (28%), 'Law Enforcement and Public Safety Professionals' (14%), 'Social Work Associate Professionals' (12%), 'Legal Professionals' (9%), and 'Education Institutions Teaching Professionals' (6%). The top five themes for what adolescents were most proud of about themselves were 'School performance' (22%), 'Outward appearance' (15%), 'Sports skills' (12%), 'Personality' (11%), and 'Behaviour at home/with elders' (7%). Adjusted analysis showed no evidence that HIV status was associated with important differences in aspirations or self-perceptions. In conclusion, adolescents facing high levels of adversity in South Africa hold high value for their education and aspirations for their futures. Policies and initiatives should focus on meeting these aspirations as vehicles for development, independent of their HIV status. Therefore, more needs to be done to not just help adolescents survive but thrive into adulthood.