Aim of this paper is to explore some crucial factors playing a significant role in employment decision-making in a generational perspective and in an extensive international comparison. The work intends to evaluate how the intergenerational transfer of human, social and financial capital may vary across a selected set of developed economies of Western Europe, taking into account the different institutional settings and macro-economic or cultural contexts. At this end, a series of three-stage structural multinomial logit models with latent variable is estimated and endogeneity and selectivity issues are dealt with. In brief country-specific differentials are sketched and the often controversial role of each national welfare regime in shaping self-employment patterns is widely discussed.