This article describes the results of a qualitative pilot study, conducted with individuals facing multiple statuses of marginalisation and self-reported barriers to formal education (n = 8). This study emphasises the potential utility of fictional media based on narrative or storytelling pedagogies, and posits that the increasing use of arts-based methodologies and media for knowledge translation can improve agency and access to information. With the objective of understanding how digital media contributes to self-initiated lifelong learning, participant responses with specific relevance to mental health are analysed under a transformative learning framework. Results indicate that digital media (1) often takes on a personal nature, resulting in reflections on experiences of trauma; (2) may present an inequitable distribution of negative impacts to individuals who already face marginalisation; (3) is accessed by participants in search of community, while simultaneously creating notable isolation; (4) is affected by the construction of ideologies around digital media, which potentially undermines its potential as a learning tool. Towards supporting the creation of digital media which successfully reduces inequalities in lifelong learning, 18 design considerations conclude this article.