Orientation: Leaders must understand how to manage digital nomads in their companies. Research purpose: This study aimed to explore how digital nomads’ experiences shape their understanding of their work and life during the transitional career process. Motivation for the study: Little research explores why individuals become digital nomads and what they find important in their life and work. Research approach/design and method: This study employed the concept of working identity and used the open-ended approach of grounded theory. The snowball sampling method was used to recruit the participants, and data were collected using semi-structured interviews with 28 digital nomads. Main findings: The authors identified five stages related to how digital nomads’ experiences shape their views on what matters most to them in work and life: (1) rebelling against established work norms, (2) experimenting with ways of working and living, (3) crystallising personal work and life values, (4) living new work and life scripts and (5) rebelling against a nomadic lifestyle. Practical/managerial implications: This study provides useful findings for managers who are working in business strategy and policy settings and are seeking to recruit digital nomads. Career counsellors could also use this study’s findings to help individuals develop realistic expectations about the lifestyle and careers of digital nomads. Contribution/value-add: This study builds an understanding of nomadic experiences from a career exploration perspective and offers recommendations for future research on the role of luck in digital career paths and career decisions.