Why do some young people make smooth transitions into the labour market while others do not? Sociological accounts typically view the risk of ‘bad beginnings’ in the labour market through a micro-macro framework: risk is the function of individual characteristics and national institutional arrangements. In the first part of my thesis I explore the impact of spatial inequality – understood here as spatial variation in the number and type of job vacancies available within countries – on this pivotal life course transition. I ask: what happens to young people in places where opportunity doesn’t knock? The first three papers capitalise on the availability of comparable panel data from the United Kingdom and Germany to explore the consequences of spatial inequality in two contrasting institutional settings. In both countries, I find that spatial opportunity structures substantially moderate the size of the labour market penalties associated with known micro-level risk factors. The overall pattern is consistent across the various methods and measures of youth labour market outcomes that I employ: strong local opportunity structures tend to equalise outcomes, whilst weak opportunity structures tend to exacerbate the differences between young people based on educational attainment or social origins, net of educational attainment. These findings are important in and of themselves, since early experiences have long-term consequences and labour market processes form the central mechanism of distribution in society. But they assume new significance in light of claims that the increasingly unequal geography of opportunity is responsible for the growth of support for populist politicians and radical right parties. The fourth paper therefore considers whether and how much changes in the opportunity structure affected support for Brexit in the 2016 EU Referendum in the United Kingdom. It shows that locally rooted individuals – defined as those living in their county of birth – were more likely to support Leave, but only if living in places that have experienced relative economic decline or increases in migrant populations in recent years. In combination, these papers make an important contribution to enhancing our understanding of the spatial or contextual roots of socio-political phenomena.