This exploratory essay coins the term "academic pathologies' to discuss in a critical approach the culture of the academic self while focusing on the anxieties of knowledge. The chapter plays with these themes in reference to the work of Kierkegaard, Wittgenstein, Foucault, and the American film director Woody Allen. The author contends that this topic has eluded him over the years while he was trying to grapple with various formulations. The resulted text that follows the history of the author's many, and often failed, attempts is an exercise in self-therapy, confession and self-examination with regard to his contesting to a pervasive ability/inability to produce this essay. The chapter is asking a persistent question of what a process of becoming "academic self' may mean for women, for Maori, for other cultural minorities or immigrants, or for those for whom thinking and writing in ideographs is the cultural norm. The interplay of re-reading and re-writing in the midst of the revaluating some of the author's life-experiences coupled with a type of philosophical exegesis, is an authentic example of edusemiotics in action as it focuses on a lifelong process of self-formation.