The purpose of this paper is to reveal a set of new results obtained from an ongoing investigation focused on the way that the particular characteristics which are inherent to “wannabe” digital nomads’ activities contribute to the sustainability of the whole digital nomad ecosystem. In line with the premise of this research, we assume the importance of understanding the impacts that are being felt in the personal knowledge management ecology practices and routines of digital nomads as experienced by a specific online population (i.e., Reddit user base), together with a deep and wide examination of their preferences and expectations regarding the technology-mediated work-life issues that exert a direct influence on the digital nomad community. To this end, we gathered and further processed text posts and comments from users in the ‘/r/digitalnomad’ subreddit. From a sociotechnical standpoint, the empirical data extracted from this sample population about the wannabe/how to be digital nomad symbiotic ecosystem can provide insightful information for researchers worldwide about future design-level interventions.