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This paper examines how drawing skills can be taught to unemployed youth in under-resourced contexts to support the expression of their lived experiences during the COVID-19 pandemic. Framed within a vocational education and training (VET) skills ecosystem orientation, the study positions creative skills development as part of broader human development and livelihood sustainability initiatives in informal settings. The paper aims to explore the potential of arts-based research (ABR) as a pedagogical and methodological approach for developing 21st-century skills, with a specific focus on drawing as a tool for communication and reflection during a crisis. We employed a qualitative arts-based research design that combined creative workshops, visual artefacts, and participant reflections. Due to pandemic-related restrictions, the research design was adapted to a digital environment, with WhatsApp used as the primary platform for skills instruction, interaction, and data collection. The dataset comprised visual drawings produced by unemployed youth participants, reflective narratives, and facilitator observations generated during a series of online creative workshops. The qualitative and visual data were analysed thematically, resulting in six key themes that captured participants’ experiences of unemployment, uncertainty, resilience, identity, and the challenges of learning creative skills in a digitally mediated, resource-constrained context. The main findings demonstrate that (i) drawing skills can be effectively taught using low-cost digital platforms, even in under-resourced settings; (ii) creative processes enable unemployed youth to articulate and reflect on their lived experiences during a pandemic; and (iii) a VET-oriented skills ecosystem provides a useful framework for situating arts-based skills development within broader livelihood and social support structures. Despite a small sample size, the study contributes practical insights into conducting arts-based research during crises and offers guidance for integrating creative skills development into informal youth skills ecosystems.