This chapter describes the author attempt to 'study up' through colonial hierarchies and across cultures; an unsettling process that turned over rocks for both the researcher and the researched. It contributes to and extends the useful discussions; studying up colonialism, former colonial agents, and past colonial projects and processes involves additional challenges that are not yet well represented in elite or whiteness studies. The chapter discusses some of the cross-cultural, ethical, personal and emotional dilemmas, and some of the tensions and insights gained from 'studying up' colonial subjects and colonial power in the transformative spaces between Indigenous and white Canadian cultures. An examination of colonization and studying up colonial settler-descended peoples involves confronting fragile myths of Euro-Canadian superiority and manifest destiny that continue to shape our present day national image. Crean describes this as taking ownership and 'understanding the how, who and why' of colonizing projects like the Indian residential school system.