To access the benefits of mobility, digital nomads regularly disconnect from their physical locations, which should prevent them from forming a sense of place. Yet, they need this sense of place to work effectively and continue to work as digital nomads. Identifying this tension between mobility and work as the mobile worker paradox, we conduct a qualitative analysis of 73 interviews with 67 digital nomads and advance a theoretical model showing two paths by which digital nomads navigate this paradox. As digital nomads initially move to a new location, they experience placelessness—enjoying freedom and being burdened by the lack of structure. They use their freedom for nonwork adventures, and they address burdens via work placemaking, resulting in placefulness, which is a deep connection to their physical location. We find that digital nomads interpret placefulness differently according to their degree of wanderlust, which determines whether they navigate the mobile worker paradox through place iteration or place integration. Challenging the idea that mobility and a sense of place are incompatible, this study enhances our understanding of digital nomads and mobile workers broadly, and it contributes to the literatures on place, paradox, and flexible work. It also invites further research on hybrid workers, the importance of wanderlust in contemporary work arrangements, and the career implications of place iteration and place integration.