Most studies have shown that self-employed people have higher levels of life satisfaction than employed people due to high levels of job satisfaction, work flexibility, and job control. However, during the COVID-19 pandemic, many self-employed people experienced economic strain and worried about the situation of their employees and survival of the company. The aim of this study was to examine the level of life satisfaction among self-employed people during the COVID-19 pandemic in different welfare regimes. Analyses were mainly based on Eurofound’s “Living, Working and COVID-19” online survey. Fieldwork took place between April and June 2020 in 27 EU countries. The results showed that there was a significantly lower level of life satisfaction among self-employed people than employed people during the pandemic. This was in contrast to analyses from approximately one year before the pandemic, which showed that life satisfaction was higher among self-employed people. The main reasons for this lower level of life satisfaction among the self-employed during the pandemic were worse household financial situation and more worries about their job. Analyses of life satisfaction among the self-employed in different welfare regimes indicated that self-employed people in the Nordic welfare state regime largely kept their relatively high level of life satisfaction during the pandemic, but this was not the case for self-employed people in other welfare regimes.