Years ago, Herbert Simon suggested that the standard assumption of rational choice theory, that decision makers choose so as to maximize expected utility, is psychologically implausible, because maximization requires cognitive operations that exceed human capacity. Simon proposed, instead, that people “satisfice,” choosing “good enough” rather than the best options. The maximizing challenge is exacerbated when choice sets are large, as is the case with most of the decisions people face in modern, affluent societies. More recent work has identified individual differences in decision making, with some people aiming to maximize and others aiming to satisfice. Maximizers make better decisions than satisficers, but feel worse about them. In this talk, I will suggest that the goal of maximizing is not just a psychological mistake, but an epistemological one—that often it is not possible. I will also present new empirical work that shows that when choice sets are large, people view choices as self-expressive, making even seemingly trivial decisions (e.g., what jeans to buy) into significant ones, and that when this happens, it enhances the tendency to maximize in making these decisions. In other words, large choice sets raise the stakes of decisions, turning people into maximizers, which results in less satisfying decisions. I will finally suggest that perhaps viewing the self as “achieved” rather than as “ascribed,” or the self as “incremental” rather than as an “entity” may be a mixed psychological blessing. If there is a secret to happiness, it may be, as Aristotle said, in finding the mean between too much freedom and too little—between standards that are too high and standards that are too low. Chris Peterson taught us many invaluable lessons about happiness in his distinguished career, and I do not think he would be surprised by this one.