This chapter moves away from the more textualist approach adopted heretofore in the philosophical and literary discussions of narrative identity, digitality, and wellbeing. In employing a transdisciplinary ethos and elements of interdisciplinarity, the chapter employs a psychological approach to examine the relationship between narrative identity online and psychological wellbeing. Transdisciplinary research (TDR) has been described as research that focuses on a “complex problem that cannot be solved by methods, concepts, theories, and knowledge produced by a single or even multiple disciplines. It requires another fundamental component, society” (N. Rezaei, 2022, p. 4). How narratives of identity mediate the wellbeing of young people in a digital age is one such complex problem that necessitates collaborative work across disciplines while at the same time working with users, stakeholders, and young people to produce new insights. While interdisciplinary research is described as also involving work from various disciplines in solving a common problem where researchers enrich their knowledge with ideas from methodologies from different areas in making disciplinary boundaries transparent, there is perhaps less focus on the input of users, stakeholders, and non-experts. As discussed, my interest in narrative identity emerged from readings in literature and philosophy. However, narrative identity is also an important concept for the social and behavioural sciences, for counselling practice, and for education studies. The transdisciplinary impetus of this project arose from frustrations in regard to the difficulty of bringing insights around narrative identity from different disciplines and practices together to foster collaborative enquiry. The work of this chapter offers one example of such collaborative work. It describes a psychological experiment conducted into the relationship between narrative identity online and psychological wellbeing. The project involved the use of experiment-building software, statistics software, and quantitative and qualitative methods. The insights from the philosophical works and literary narratives examined in the previous chapters offer important speculative insights that inspired the motivations for the experiment. For example, literary theorist Spencer Jordan regards smartphone app-based texts and other born-digital texts as inaugurating a new mode of embodied exploration for readers that does not do away with physical materiality but instead introduces a “hybridic mix of body, movement and text” as a new kind of “embodied space” (198). Materiality is as important as ever, he argues, in granting a “reenchantment with authentic experience”. Spencer also argues that these new digital texts inaugurate a new sense of conflict for readers. However, literary studies typically have no way of assessing the nature and verifiability of such claims in relation to the emotions of readers. Psychological studies have also conducted experiments to examine the nature of the “hybrid reality” young people inhabit in navigating lives between online and offline practices. This chapter, therefore, practices an interdisciplinary approach in taking insights from how literary studies and philosophical studies describe the relationship between narrative and wellbeing and testing them out using a psychological experiment on narrative identity and psychological wellbeing. The insights from literary studies inform the psychological investigation into the relationship between narrative identity and psychological wellbeing.