This study endeavors to outline the parallel paths taken by three D/Lakota individuals who lived at the beginning of the twentieth century and wrote about their experiences within the federal Indian school system that sought to assimilate them into mainstream society. Through Charles Alexander Eastman’s, Zitkala-Sa’s and Luther Standing Bear’s perspectives, this study brings together memories of their experience as students and educators, and underlines their profound attachment to their Indigenous culture. Besides, the very fact that they wrote their autobiographies in an attempt to counter stereotypes and have their voices heard participates in this resistance, as they become the ones defining the terms.