This article considers the growing lifestyle trend of digital nomadism, whereby individuals leverage digital technology to combine work, leisure and hypermobile travel interests. Based primarily on ethnographic fieldwork in Chiang Mai, Thailand, I examine the lifestyle and mobility pathways of digital nomads through two distinct yet coexisting notions of disruption. On one level disruption is viewed as a radical expression of flexibility, fluidity and newness, that evokes a sense of breaking free from a traditional past. At the same time, I consider disruption on more subtle terms, addressing ways in which historical formations pertaining to work and tourism feed into and unsettle understandings of self, place and mobility. In this article, I examine the role of a work-leisure distinction, colonial imaginaries of place and emerging norms of hypermobility in complicating attempts by digital nomads to establish a coherent sense of self, work and productivity in and across tourism destinations. These seemingly fluid lifestyle practices, I suggest, promote a continual preoccupation with boundaries, as digital nomads try to make sense of work, identity and newness amid an in/visible and intersecting constellation of mobility pathways involving Western backpackers, Chinese tourists, resident foreigners, visiting family and friends, and other nomads.