Poverty and inequality have risen dramatically in Britain since the late 1970s leaving the country today with one of the lowest levels of social intergenerational mobility in the developed world. Drawing upon qualitative research in one particularly disadvantaged and deprived region of the UK, this study explores the impact of social, political and economic change over the past three decades on contemporary youth transition. Set against the current backdrop of economic austerity, diminishing youth entitlements and social exclusion. The research explores five individual biographies from a diverse sample of 28 disadvantaged young people as they carve out their transition to adulthood in adverse circumstances. From this the thesis identifies a number of what appear to be indicative patterns connecting macro socio-economic transformations to the micro environment of young people. Overall, the intention is to illustrate and broaden the current understanding of the difficulties and complexities disadvantaged young people face in their school to work transition in a setting where disparities of wealth, income and opportunity are growing.