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According to self-regulation theories, affect plays a crucial role in driving goal-directed behaviors throughout employees' work lives. Yet past work presents inconsistent results regarding the effects of positive and negative affect with theory heavily relying on understanding the separate, unique effects of each affective experience. In the current research, we integrate tenets of emotional ambivalence with self-regulation theories to examine how the conjoint experience of positive and negative affect yields benefits for behavioral regulation. We test these ideas within a self-regulatory context that has frequently studied the benefits of affect and has implications for all employees at one point in their careers: the job search. Adopting a person-centered (i.e., profile-based) perspective across two within-person investigations, we explore how emotional ambivalence relates to job search success (i.e., interview invitations, job offers) via job search self-regulatory processes (i.e., metacognitive strategies, effort). Results illustrate that the subsequent week (i.e., at time t + 1; Study 1) and month (Study 2) after job seekers experience emotional ambivalence (i.e., positive and negative affect experienced jointly at similar levels at time t), they receive more job offers via increased job search effort and interview invitations. Theoretical and practical implications for studying emotional ambivalence in organizational scholarship are discussed. Supplemental Material: The online appendix is available at https://doi.org/10.1287/orsc.2021.1553 .