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We examine the relationship between lateral preference, the Five-Factor Model of personality, risk-taking propensity, and maverickism. We take an original approach by narrowing our research focus to only functional aspects of maverickism. Results with 458 full-time workers identify lateral preference as a moderator of the neuroticism–maverickism relationship. Extraversion, openness to experience, and low agreeableness were also each found to predict maverickism. The propensity of individuals high in maverickism to take risks was also found to be unaffected by task feedback. Our results highlight the multifaceted nature of maverickism, identifying both personality and task conditions as determinants of this construct.