In this paper we contend that the socio-economic context shapes the opportunity structure for the younger generation and thus their individual decisions on the labour market between dependent employment, self-employment and entrepreneurship. Building on the varieties of capitalism approach, we expect that entrepreneurial behaviour is more pronounced in liberal market economies than in coordinated market economies with encompassing welfare states. To assess the plausibility of this argument, we use CUPESSE project survey data to compare occupational choices and welfare attitudes of respondents aged 18 to 35 in Germany and the United Kingdom, a typical CME and LME respectively. We analyze behavioural differences in the three subsystems of the varieties of capitalism approach covered by CUPESSE data: corporate governance and financing, skill creation, and decommodification and welfare state. Our preliminary results show that inter alia respondents from the UK consider job-specific skills and a good general education as less important to find a job, are more willing to retrain to find a job, more often deem themselves overqualified for their current job, and are in general more willing to take risks.