Digital storytelling has been applied in research in varied contexts and with varied purposes. Implicit in the process of digital storytelling is the potential to develop and/or enhance a range of individual skills (e.g., multimedia, literacy, communication, etc.). However, further research is needed to gain a deeper understanding of the potential impact of digital storytelling on skill enhancement for disabled youth. This paper provides an overview of Phase 1 of the study “My life. My story: The Youth Digital Storytelling Project” that utilized elements of a community-based participatory action research approach to host a peer-facilitated digital storytelling workshop for young adults with developmental disabilities aimed at capturing and sharing their lived experiences with, knowledge of, and perspectives on significant life-stage transitions in the areas of education, employment, or living. The results from the pre- and post-workshop questionnaires suggest that the participants improved skills in media literacy, communication, and leadership. Additionally, the participants highlighted the importance of considering the delivery format, fostering connections, and enhancing self-confidence in the development of the workshop’s design and delivery. This research adds to the extant literature demonstrating the potential of digital storytelling as a pedagogical tool, offering implications for the design and implementation of online workshops for disabled youth.