Digital storytelling is a decentering methodology in health promotion that positions the storyteller as an expert to create a narrative of their lived experiences. This article describes using a two-phase digital storytelling process within the Diné (Navajo) Educational Philosophy framework to guide the development of a culturally grounded curriculum plan that actively engages Diné youth in exploring health professions pathways in their community. The first phase consisted of developing a high school digital storytelling team by training three Diné youth attending high school on the Navajo Nation located in southwest United States, in digital storytelling. In the second phase, the high school digital storytelling team worked collaboratively with seven Diné students enrolled at the local tribal college to develop digital stories about navigating from high school to college. Data from seven completed digital stories were analyzed with assistance from a community advisory board to identify asset-based themes that contributed to positively transitioning from high school to a tribal college. The results revealed several strategies for successful transitions from high school to a public health college major. The culturally relevant strategies and stories were incorporated into a school-based health professions pathway curriculum plan for Diné youth.