Abstract: The new world of work offers unprecedented opportunities for holding more than one job. Existing research has emphasized that involvement in multiple jobs is a demanding experience that ultimately promotes burnout. Recent research has also suggested advantages of multiple jobholding. Notably, these contrasting perspectives about the burdens and benefits of involvement with multiple jobholding have generally been presented in fragmented accounts. We offer a more comprehensive and balanced treatment of these divergent viewpoints by drawing on the job demands resources framework—an approach that encourages a holistic account of how involvement in a given work arrangement relates to burnout via demands and engagement via resources. We first address the implications of multiple jobholding involvement for work- and home-related demands that, in turn, promote burnout. We complement this consideration of the demands associated with multiple jobholding by building upon assertions about how and why holding multiple roles generates psychological and material resources within the work and home domains. Specifically, we theorize that multiple jobholding involvement promotes resources—psychological capital in work, work-home enrichment, and income—that ultimately foster engagement. We found general support for our model in a three-wave field study involving 250 multiple jobholders. We also present a supplemental dominance analysis regarding the relative effects of various demands and resources. Overall, we offer novel and important insights about how and why multiple jobholding involvement concurrently generates unique demands that drive burnout, as well as resources that promote engagement.