|This study is motivated through the paradox on the well-being of self-employed that self-employment is associated with greater satisfaction across various domains despite the lower income levels of such entrepreneurs. Since not all self-employed gain higher returns to income, there is a need to question to what extent income contributes to well-being as well as the most critical factors such as education or the reason that the entrepreneur starts a new business could play a role in this relationship between income and well-being. Using GEM’s data on entrepreneurs from a wide set of countries all over the world, the effect of income on entrepreneurial well-being is tested treating education as the moderator across necessity and opportunity entrepreneurs. While necessity entrepreneurs with relatively lower education levels gain higher returns to income, opportunity entrepreneurs gain higher returns to income when their education levels are higher. The results shed light on how the effect of income on entrepreneurial well-being changes adversely with the increasing education levels for different entrepreneurial motivations.