Adding to prior literature that has examined the relationship between maximization and dissatisfaction, the present research suggests that maximizers, as defined by the original maximization scale, are unhappier decision makers than satisficers because maximizers fail to adequately handle dissonant experiences. Throughout three studies that use different conceptualization and measurement of maximization, we show that maximizers are more vulnerable to negative feedback about one’s choice such that they decrease positivity toward the chosen option to a greater level than satisficers. However, this effect was mainly driven by the decision difficulty factor in the conceptualization of maximization. When decision difficulty was conceptualized as a defining component of maximization (Study 1 and 2), “maximizers” show greater positivity drop in the face of negative feedback. However, in the absence of a decision difficulty component, a recently proposed two-component model of maximization (the goal to get the best and search for alternatives; Cheek & Schwartz, 2016) did not play a significant role in predicting positivity drop, while perceived decision difficulty did (Study 3). Together our findings suggest that previously reported contradictory outcomes of maximization may be due to inconsistent conceptualization and measurement, especially treating decision difficulty as a defining component of maximization.