Previous research shows that the self-employed generally experience a higher degree of job satisfaction compared to regular employees. However, our knowledge of subjective well-being among the self-employed, the differences between various groups of self-employed and the potential influence of contextual factors is somewhat limited. The purpose of the present paper is to address this gap by taking macroeconomic conditions, gender and immigrant status into consideration. The results show that self-employment is positively related to subjective well-being, but there are also differences between groups of the self-employed; self-employed with employees report a higher level of life satisfaction than the self-employed without employees. Economic growth is more important for the level of life satisfaction among the self-employed than among employees. The analyses also point to different patterns for female and male self-employed without employees: only women experience a higher level of life satisfaction compared to employees. The results also show that the relationship is stronger among immigrants than natives. The results of this study confirm the importance of considering potential heterogeneity when examining subjective well-being among the self-employed.