The purpose of this exploratory study is to examine the role of satisfaction and subjective well-being (SWB) in occupational choice. We focus our attention on the diversity of determinants of satisfaction with life for employed and self-employed individuals. Job satisfaction is a most studied variable, object of a lot of attention and of extensive literature, but seldom used in entrepreneurship studies. Not much research has been carried out to understand the effect of SWB on the decision to choose employment or self-employment. A closer look at the determinants of decisions, motivation and commitment of people whether employed or in charge of a new created organization will shed light on elements which individuals and society value beyond wealth. For M. Csikszenmihalyi (1990) the quality of experience in life is a function of the relationship between challenges and skills. Optimal experience, or flow, occurs when both variables are high.