The evolution of discourse about digital storytelling in education has moved from technology training to assessment and portfolio to a more fundamental understanding of story-based pedagogy as a tool for transformative learning. This chapter considers the lynchpin on this dialogue about digital storytelling, story facilitation, and story work in education. Brooke Hessler done national and international works as a faculty development facilitator and is a member of the international working group on digital storytelling in higher education. Once upon a time, digital storytelling was proposed as a short cut to filmmaking, to the painstaking process of creating short and medium-length multimedia documents, in which endless planning, reflection, iteration, and review was necessary. How digital storytelling as a form oriented toward "Every Story Matters" in the classroom or society at large, meaning one that is broadly democratic and inclusive, for spending time, time that is precisely the problem for many educators who want to use digital storytelling in their classrooms.