This thesis explores the transitions of young people from different national, social and cultural groups into post-compulsory vocational education and training (VET) and technical careers in the State of Qatar. It aims to understand young people’s perceptions of post-compulsory VET and technical careers, the factors that enable or constrain their participation in engineering and skilled trades programmes, and their strategies for navigating education and employment. The thesis employs a qualitative research design and in-depth interview methodology to investigate the subjective transition experiences of 15 young people from diverse national, social and cultural backgrounds participating in engineering and skilled trades programmes at three post-compulsory institutions in Qatar. The data were analysed according to a thematic framework based on a priori codes, which resulted in several inductive themes. The findings indicate that although young people are positive about post-compulsory VET and technical careers, higher education (HE) remains the normative pathway for college-bound students. However, a growing number of young people participate in VET to circumvent barriers to HE and enter the thriving technical labour market. They use economic, social and cultural capital to navigate these barriers, which include Qatar’s segmented labour market, academic requirements, institutional habitus, social networks and social positioning. Differently situated young people reflexively fashion their transition biographies to celebrate successes and rationalise failures in Qatar’s dynamic post-compulsory education system and technical labour market.