This paper endeavours to inquire into the multi-dimensional nature of psychoanalytical knowledge, and the narcissistic investment of analysts in their theories. It will explore the challenges this combination poses to a profession where the object of study is, in part, constitutionally elusive to logical-rational argumentation, or empirical findings, and how the lack thereof is often substituted by a potentially blinding personal involvement with it that is, at the same time, indispensable to function as an effective clinician. This thorny paradox can leave psychoanalysts in an ineffectual position when it comes to controversies, particularly if they are unequipped with epistemological and methodological tools to resolve the category of problems they are confronted with. These tools include: establishing clear distinctions between orders of psychoanalytical knowledge, comprehending the leaps of inference made between the clinical-theoretical gap, being aware of the distorting effects uncertainty has on thinking, and discriminating between convictions and persuasions. Some ideas as to how we could fruitfully address these difficulties, and what direction we might consider going in to advance our discipline, will be offered in conclusion.