This theoretical paper explores the use of online journaling in an educational administration program to interrogate spaces of “otherness”—the geographical spaces of cities where poor children and children of color live—and the dangerous memories prospective administrators may have about diversity. The cultures of most educational administration programs do not help graduate students “dig beneath the surface” of the seemingly benign recipes of current school reform to explore cultural differences. When given the opportunity to use reflective online journaling, candidates talked more freely about race, ethnicity, class, language, ability/disability, gender, sexual orientation, and other facets of diversity. Reculturing educational administration programs will require both students and instructors to have similar opportunities to interrogate spaces of “otherness” and work to transform them.