The intersection between the work and nonwork domains is increasingly blurred, which calls for scrutiny of how the latter can be enriched by demands faced at work. The literature suggests that work challenges can enhance, and hindrances tend to conflict with, the nonwork domain. However, the literature is silent on the interactive pattern between challenges and hindrances, and, more importantly, the role that attitudes toward learning play in work demands interfering with the nonwork domain. We theorize that the more learning-oriented individuals are, the easier they find it to leverage the nonwork-benefit potential of challenges and avoid the nonwork-threatening potential of hindrances in the presence of the respective other. We used hierarchical linear modeling on experience sampling data of 1,134 paired evening—morning observations of 144 professionals to test our theoretical assumptions. Our multilevel analyses confirm not only that challenges enrich, and hindrances conflict with, the nonwork domain, but also that both may spill over via the other's mechanism as a function of the other. More specifically, on particularly challenging days, highly learning-oriented individuals are found to even enrich their nonwork life through the experience of hindrances. The resulting theoretical and practical implications are discussed.