Maximization refers to a decision-making style that involves seeking the single best option when making a choice, which is generally dysfunctional because people are limited in their ability to rationally evaluate all options and identify the single best outcome. The vocational consequences of maximization are examined in two samples, college students and working adults. After controlling for trait perfectionistic striving, highly maximizing students reported lower satisfaction and perceived fit with their majors, higher academic turnover cognitions, and lower career decision self-efficacy (Study 1). Similarly, highly maximizing adults reported less satisfaction and perceived fit with their jobs, higher employment turnover cognitions, and less satisfaction with the progression of their careers (Study 2). In both studies, the relations of maximization and these outcomes were mediated by negative affect, pointing to feelings of regret and frustration as a mechanism that drives these negative appraisals. Implications for practice and directions for future research are discussed. (Contains 4 tables.)