Many students in Portland’s schools face racism and other forms of discrimination on a daily basis. Storytelling is a practice that is fundamental across all cultures and provides a vehicle that students from all backgrounds can access as a mechanism for engaging in the development of their academic identity. This article shares about how a digital workbook assignment was designed as an outlet for student self-expression dealing daily with racism and prejudice related to systems of oppression in education and the rapidly changing and evolving life of a city.