Prior to the first chapter, Taleb writes briefly about the library of writer Umberto Eco. He calls it an "antilibrary," in which Eco valued the books he hadn't explored much more than the ones he had already read. The central premise is this: The knowledge we have not yet acquired leads us to being openminded to life's possibilities, informed by knowledge but not protective or possessive of it like personal property. Taleb then delves into the first chapter, which deals mostly with his formative years in Lebanon and his subsequent departure during Lebanon's civil war. These experiences led to him becoming a skeptical empiricist, as he tried to process highly impactful global events, such as the war in Lebanon and the stock market crash of 1987. These Black Swan events revealed to Taleb that humanity by and large is blind, given the pervasiveness of these types of highly unlikely, virtually unpredictable events.

Thematically, the first chapter is most connected to the concept of human nature, particularly around the human tendency to oversimplify or overlook Black Swan events. According to Taleb, human beings claim to know much more than they do, as suggested by the total shock that accompanies a Black Swan.