The Big Five personality traits have been linked with a broad range of consequential life outcomes. The present research systematically tested whether such trait–outcome associations generalize across gender, age, ethnicity, and analytic approaches that control for demographic and personality covariates. Analyses of nationally representative samples from the Life Outcomes of Personality Replication project ( N = 6,126) indicated that (a) most trait–outcome associations do generalize across gender, age, and ethnicity; (b) controlling for overlap between personality traits substantially reduces the strength of many associations; and (c) several dozen trait–outcome associations proved highly generalizable across all analyses. These findings have important implications for evaluating the robustness of the personality–outcome literature, updating the canon of established trait–outcome associations, and conducting future research.