How might digital technologies (DTs) support creative expression and, in the process, reframe failure as a productive feature of creative learning endeavors? The purpose of this conceptual article is to provide a way of approaching this question. More specifically, the article opens with a brief discussion highlighting how DTs have the potential to support creative learning and adaptive conceptions of failure. The discussion focuses on the importance of recognizing "how" educators and students use technologies is more important than "what" particular technologies are used in support of creative endeavors. Next, the article provides an example of a particular creative curricular experience, called "My Favorite Failure," which serves as a context for how educators and students can experience the positive reframing of their own and other's failures through digitally supported narratives. Considerations for how educators and students might use digital technologies to support this particular type of creative experience as well as creative learning more generally are also discussed. The article closes by outlining next steps for educators, students, and researchers.