This article analyses the phenomenon of self-employment and entrepreneurship among the 20– 35-year-olds in the two country contexts; Poland and Ireland, and the capital cities ofWarsaw and Dublin, respectively, in 2005. It seeks to compare motivations driving the choice of an autonomous style of work; role of social capital both for decisions to start up as well as for subsequent economic performance; the value of an institutional environment for entrepreneurial efforts. It examines such aspects through the prism of the economic and socio-cultural characteristics of the countries in question. By this, the article draws a broad picture of findings that may inform individual as well as macro-related characteristics of entrepreneurship