Education is considered one of the most critical human capital investments. But does formal educational attainment "pay off" in terms of job satisfaction? To answer this question, in Study 1 we use a meta-analytic technique to examine the correlation between educational attainment and job satisfaction (k = 74, N = 134,924) and find an effect size close to zero. We then build on the job demands-resources (JD-R) model and research that distinguishes between working conditions and perceived stress to theorize that educational attainment involves notable trade-offs. In Study 2 we develop and test a multipath, two-stage mediation model using a nationally representative sample to explore this idea. We find that, while better-educated individuals enjoy greater job resources (income, job autonomy, and job variety), they also tend to incur greater job demands (work hours, task pressure, job intensity, and time urgency). On average, these demands are associated with increased job stress and decreased job satisfaction, largely offsetting the positive gains associated with greater resources. Given that the net relationship between education and job satisfaction emerges as weakly negative, we highlight that important trade-offs underlie the education-job satisfaction link. In supplemental analyses, we identify boundary conditions based on gender and self-employment status (such that being female exacerbates, and being self-employed attenuates, the negative association between education and job satisfaction). Finally, we discuss the practical implications for individuals and organizations, as well as alternative explanations for the education-job satisfaction link. (PsycInfo Database Record (c) 2022 APA, all rights reserved).