Happiness has intrigued humans probably since the beginning of time although the forms of pursuing it as well as ways of enjoying it may have varied greatly (Plutchik 2003; Kim-Prieto, Diener, Tamir, Scollon& Diener 2005). In modern western societies the chase of individual happiness has become a driving force affecting even stability of families (Sund & Smyrnios 2005) these days. At the same time stress and anxiety seem to have reached epidemic proportions (Dozois & Dobson 2004) with enormous costs attached to them (Hudson, Flannery-Schroeder & Kendall 2004). Both general interest in and academic writing on happiness has grown markedly during the latest years yet studies concentrating on entrepreneurs are remarkably few. This study seeks to address three issues. Firstly, to compare the level of experienced well being to find possible similarities and differences between entrepreneurs and employees. Secondly, to look at the individual construct of experienced well being on average in each group and thirdly to establish patterns – system dynamic models - specific to entrepreneurial well being.