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The chapter addresses the questions surrounding the politics of the academe as a reflective process. The three authors’ experiences are very different – spanning from tenured professor to sessional instructor to professor in an African university. The narratives from the authors inform the readers of their goals to join the academy as faculty; their job search; being members of the staff and then; their experiences as members of the teaching force at various universities. The chapter is based on their experiences of navigating the politics of the academe. This chapter provides their narratives of what it means to be a professor, mentor, colleague, and researcher. Each story is told from their particular standpoint: two females and one male teaching in North American universities and Africa, respectively, two Black and one racialized female who can pass, but cannot because of her name. The analysis will address numerous complications involved in addressing expectations, establishing common grounds as educators from an international perspective, and providing narratives of how we have managed to maintain our goals and aspirations as members of the academe. The tensions involved will be problematized and explored from within the context of the academy and the associated constraints therein (Tatum, 1999). The objective of this chapter is to theorize the significance of navigating the politics of the academe to deflate arising tensions that may delay your passion for teaching. The chapter is informed by an anticolonial theoretical framework in light of converges and divergences of varying colonial contexts embedded in colonial Canadian society. The anticolonial framework draws on the specific settler-colonial Canadian context (Tuck & Yang, 2012). The chapter is divided into six parts: (1) introduction that provides a general overview of what it means to be faculty at a university, (2) situating ourselves, (3) theoretical framework, (4) Universities in general and more specifically, Canadian system and Kenyan, (5) discussion that provides an analysis or synthesis of our experiences, and (6) conclusion.