<p>This study explores the well-being of self-employed individuals through the lens of Desire Satisfactionism, addressing the need for a more nuanced approach to well-being assessments that accounts for the heterogeneous desires of self-employed individuals. Prior studies have predominantly applied hedonic and eudaimonic well-being frameworks, often overlooking the complexities of individuality in self-employment. In this qualitative study, we conducted 19 phenomenological interviews with self-employed individuals who were previously wage earners. Using Braun and Clarke’s framework for thematic analysis, we identified five core desires that operationalize well-being for the interviewees: good financial status, a satisfying career, work-life balance, good health, and feelings of safety. Despite numerous unfulfilled desires, participants reported high overall well-being and, in most cases, a strong intention to continue in self-employment. This paradox suggests the presence of a <i>Compensatory Desires Effect</i>, whereby the fulfilment of certain core desires exerts a disproportionately positive influence on subjective well-being, mitigating the adverse effects of unmet desires among the self-employed. Regarding its practical implications, the research underscores the importance of self-reflection and strategic planning among individuals considering self-employment, especially around key desires such as financial security, autonomy, and work-life balance. Additionally, it highlights opportunities for practitioners—including business mentors, wellness providers, and financial institutions—to tailor services which address unmet desires and which enhance net well-being among self-employed individuals.</p>