This thesis utilises, in the main, a unique panel survey of youth in Cape Town to gain insights into the functioning of the labour market in relation to transitions from schooling to work for youth. The Cape Area Panel Survey (CAPS) was conducted between 2002 and 2006, a period which coincides with upswing in the South African economy culminating in relatively high economic growth in recent history. The introductory chapters utilise cross-sectional data (Labour Force Survey, 2005) in order to contextualise the panel data analysis that follows in subsequent chapters. A large portion of the South African population is youth. Either this facet of the demography of the country can be converted to a positive social benefit through reaping a demographic dividend or a high price could be paid through carrying a large contingent of unemployed. Indeed, much of the country's social safety net, social returns on investments in education and health and even infrastructure depend on the absorption of youth into a productive place in society. The labour market sits centre stage of all of this. The softest version of the South African dream is that post-apartheid youth cohorts have better opportunities and possibilities than their parents. These intergenerational concerns require the delivery of better education and health care but also the opportunities to use these human capital investments in gainful employment.