This exploratory paper coins the term “academic pathologies” to discuss in a critical approach the culture of the academic self focusing on what is called “anxieties of knowledge”. The paper plays with these themes in reference to the work of Kierkegaard, the American film director Woody Allen, and Jacques Derrida. This topic and paper has eluded me over the years as I tried to gapple with various formulations. The paper that follows the history of my failed attempts is an exercise in self-therapy, confession and self-examination about my continuing in- ability to produce this paper.