It is by now well-established in the entrepreneurship literature that self-employed people report higher levels of job satisfaction compared to their employed counterparts (Blachflower, 2004) even though they work longer hours (Ajayi-obe abd Parker, 2005; Hyytinen and Ruuskanen, 2007), bring home less money (Hamilton, 2000), face more uncertainly and lower job security (Praag and Versloot, 2007), and receive less fringe benefits (Storey, 1994, ch.6). In this paper, we build on previous studies by exploring the heterogeneity of this relationship with respect to higher education. We expect that the combination between higher education and self-employment will have a synergistic effect that is larger than the sum total of these two separate effects. Self-employed people enjoy higher levels of autonomy which allows them to more freely and creatively utilize and further develop their skills learned in school and to channel their productive energy more efficiently. Higher education also establishes credibility and allows people to obtain even higher levels of certification and credibility.