This paper explores the process of obtaining creative outputs from digital workers. Specifically, we are interested in unraveling the process of transforming self-perceptions of creativity into objective other-rated creative outputs in the digital setting of crowdwork. In addition to focusing on the explanatory mechanism of creative self-efficacy, we further delve into the boundary condition related to psychological entitlement. We thereby examine the moderated-mediation model for two separate facets of the creative outputs: novelty and usefulness. We test our research model on a sample of crowdworkers (76 working professionals on Amazon Mechanical Turk) and a group of 167 digital experiment participants. The results of both studies converge in indicating that creative self-efficacy mediates the relationship between subjectively rated idea generation and the objective ratings of creative output at low and medium levels of psychological entitlement, but not when psychological entitlement was high. Specifically, this moderated mediation model was significant for novelty but not for usefulness.