Extant research that explores the motivations for self-employment has tended to focus on the motivational determinants of men’s self-employment decisions or that of the general population and there is a distinct lack of comparable work that examines the self-employment decisions of young people, in Poland and Ireland in particular. Similarly, among studies investigating the role of social capital and work experience for the choice of self-employment at the individual level, no space has been devoted to the young from these two country settings. This thesis fills such a gap and offers a comparative analysis of self-employment and entrepreneurship of the 20-35- year-olds in Poland and Ireland, conducted in 2005. It presents a comparison of motivations from a wide perspective of socio-economic context in which young entrepreneurs are embroiled. In addition, it provides analysis of social capital, work experience, institutional environment for business, and the ways of dealing with business management aspects. Yet, important input to the literature proposed by this study regards motivations to continue which evolve from the motivation for start over time when staying in business. To tackle such queries, in-depth qualitative and exploratory interviews with 40 entrepreneurs (20 in Warsaw and 20 in Dublin) were conducted. The thesis reveals that motivations do not have an association with unemployment in the Polish case and are dependent on economic growth in the Irish case. In both instances, this may be linked to the educational (human) and occupational capital, potentially increasing the likelihood of treating firm as a chance or an opportunity. Some of the motivational factors which are common to these two contexts are: desire to work for oneself, money, and dissatisfaction with work. Social capital conceived as weak and strong social ties proved to be an important factor accounting for the decision to move into self-employment and stay in it. The major differences were traced with respect to strategies and institutional assistance for entrepreneurship. The thesis may inform individual characteristics of entrepreneurship in the countries concerned. In addition, it appears as an initial step for testing the results obtained on bigger sample studies. It also formulates some tentative recommendations which may offer timely insights for decision-makers responsible for the promotion of entrepreneurship.