How can a Digital Storytelling workshop help educate, inspire and mobilise young women engaged in a non-profit organisation, in order to assist their peers? This exploratory study investigates whether Digital Storytelling can foster digital literacy, self-awareness and reflection amongst workshop participants, and how young women may be able to support each other and their peers through the act of creating and sharing personal digital stories. Conducted using qualitative and participatory methods, with the theoretical underpinnings of Albert Bandura’s Social Learning Theory and Social Cognitive Theory, Paulo Freire’s conscientisation and participatory development, this research is conducted in collaboration with female mentors from the sport-based adolescent health organisation, Grassroot Soccer. First, I analyse the women’s interactions and learnings during the Digital Storytelling workshop, where participants create digital stories in a hands-on setting (using the Story Center model). This is done through participant observation and semi-structured interviews with participants following the workshop. Second, I seek to understand how or if young women can re-present themselves in the context of a facilitated Digital Storytelling workshop and challenge gender stereotypes through their own digital stories. This data is collected through a pre-workshop questionnaire, participant observation, semi-structured interviews, and analysis of the digital stories. While this is an exploratory study, I anticipate results in the following areas: (1) cross-pollination of knowledge between workshop participants and facilitators; (2) self-awareness, self-confidence and reflection amongst young women; (3) increase in digital literacy, storytelling and audio/visual skills; and (4) increase in understanding of, or introduction to, digital media and communication, activism and social change.