The purpose of the study is to explore how the digital brand story assignment creates a transformative learning experience for students. This study involves assessing the levels of learning according to Mezirow's transformational learning theory through the development of digital brand stories. The authors have tested the Digital Brand Storytelling (DBS) video reflection assignment across two universities providing students the opportunity to meaningfully reflect on their brand relationships as part of their own personality. Study results showed that the DBS gives students an increased understanding of how brands influence their personal purchasing habits and increased awareness of the brands they purchase. Results of the study demonstrated that this assignment allows faculty to assess learning in courses where the DBS is applied toward the transformative pedagogical approach. The DBS requires reflection and articulation of personal brand attitudes, perceptions, and consumption behaviors. Guidance for course implementation is provided for educators to modify and implement in their courses.