Understanding young people’s employment experiences and transitions gives a greater appreciation of the nature of precarious work. Drawing on interview data with 30 participants from research conducted in 2011–2012, this article examines young people’s experiences of employment in the Illawarra region of New South Wales, Australia. Levels of unemployment and under-employment above the national average reflect two decades of globalised restructuring of the steel, coal and manufacturing industries which, together with agriculture, have historically been the region’s economic base. The growth of service and knowledge industries has been accompanied by new, ‘atypical’ or insecure work patterns. The interview data indicate that young people’s diverse experiences of transition and choice in leaving school, commencing training or further education, and entering the labour market are accompanied by a range of understandings of employment and precarious work. These experiences highlight the difficulties, divisions and contradictions in a changing regional labour market and suggest how the ideologies and practices of neo-liberalism shape and are embedded in regional labour markets and precarious work more generally.