The notion that people’s choices reveal something about who they are is fundamental to theories of self-perception, self-signaling, and preference construction. And yet, much is still unknown about the impact of the metacognitive experiences that accompany those choices. The present research explores how the ease or difficulty associated with choosing influences the extent to which consumers infer that they are the kind of people who are likely to make similar choices in other situations. We show through two experiments that participants believed their initial choices were more indicative of their future preferences when those choices were easy rather than difficult to make. The first experiment shows that initial lottery preferences generalize to subsequent financial decisions more readily when the choice is perceived to be easy rather than difficult, even if the difficulty is due to the superficial manipulation of the fluency of the written text in the initial choice. Our other study demonstrates that risk-taking choices would generalize more to future preferences when initial choices were relatively easy within the context online privacy. Moreover, findings from this study indicate that the relative ease of the initial decision influenced self-diagnosticity, which fully mediated choice generalization within a similar context. These findings illustrate how consumer preferences and self-concepts may be derived not only from previous decisions, but how easy these decisions felt.