This exegetical article seeks to offer a close reading of Ecclesiastes that would allow us to surmount the difficulties associated with its exegesis. The book’s text is widely known to be replete with contrasts and antinomies that introduce a certain vagueness to its writer’s intentions. The article suggests that the reader should approach the book as if it was written as a first-person logbook which appears, superficially, to have been written in no logical order, at random, and at different times (...) according to the order of the writer’s experiences and meditations. Such an approach would reduce the readers’ expectations for a logical order and would direct them to a deeper examination of the logical contexts scattered throughout the book. The article also presents the determinist con­texts of reality and their association with a wise person’s perspective as opposed to the randomness associated with a fool’s perspective. The writer’s sceptical descriptions of his encounter with reality and his first-person thoughts about this reality express an explicitly critical view of reality. The writ­er’s pre-reflexive doubt is thus nothing but a methodical doubt akin to Descartes’ pre-cogito doubts. An attentive reader will identify that the book’s text encompasses a reflexive/critical perspective on a sceptical view of reality. As such, the writer’s critical view voids the fool’s non-reflexive sceptical perspective (which is reflected in a superficial reading of the book’s text). The article’s close read­ing of the book thus posits a fool’s vanity which is a “vexation of spirit” (KJV) [re‘ut ruah․] among those who view reality as being coincidental. Conversely, it also posits a wise person’s vanity, which is a “vexation of spirit” [ra‘ayon ruah․], which critiques the fool’s pre-reflexive random view of reality as vanity and as a vexation of spirit [re‘ut ruah․]. This view of the wise person, whose “eyes are in his head” (2:14), is the true free will the writer is alluding to. (shrink)