Are self-employed workers more satisfied with their jobs compared to wage and salary workers? Using The National Survey of Families and Households: Wave I, 1987–1988, and Wave II 1992–1994 several expectations are evaluated in this article. First, self-employed persons should enjoy higher job satisfaction than others. Second, a portion of the association between job satisfaction and self-employment should be explained by higher levels of self-efficacy and by lower levels of depression among the self-employed compared to others. Third, self-employment veterans are a select group and should be different systematically from self-employment newcomers with respect to reported job satisfaction. Findings offer support for the first and second arguments above but not the third. Post-hoc analysis suggests that among the newly self-employed, the association between job satisfaction and self-employment depends on both the quantity and quality of time invested in the business. Implications of these findings and directions for further research are discussed.