For the purpose of reflective analysis, this article, which employs narrative inquiry as a research methodology, combines two "crossing the boundaries" dilemmas I experienced over the course of a decade. While the dilemmas relate to different issues that emerged in my career (standardized testing as a K-12 teacher and the formal evaluation of a reform program as a tenured, full professor), I trace the roots of the dilemmas to the same source: the hegemonic relationship between theory and practice which, despite the passage of time, continues to persist in the field of education and to shape the professional experiences of educators, some of which are miseducative. I argue that until the relationship between educational practices in schools and educational practices in universities are addressed, school reform that benefits children cannot be fully realized.