Despite the existence of a fairly strong, enabling legal and policy framework, young women in Uganda continue to face a number of challenges as they make crucial transitions into adulthood. In particular, girls are pushed into early marriages and pregnancies and are often deprived of full education attainment. These experiences are likely to have lasting impacts on their future opportunities, particularly, their engagement in productive and decent work. Using qualitative methodologies, this paper explores the inter linkages between the transitions from school to work or motherhood and/or marriage and the ensuing effects on future labour market outcomes and choices. Overall, the study finds that some discriminatory social norms and practices still exist –particularly in rural areas - and they affect the ability of girls and young women to realise their educational and economic capabilities. The majority of young people continue to be engaged in vulnerable employment with limited prospects for growth because of limited access to capital and inadequate skills to productively engage in other activities; the youth who lack skills and capital tend to get stuck in dead-end jobs. In contrast, young people with more education are likely to transit to better jobs as and when employment opportunities arise. Moreover, early fertility and marriage experiences often result in increased caring responsibilities and restricted mobility in search of employment opportunities.