The research focus of the publication is the theory of the “Black Swan” of the modern philosopher N. Taleb, which is considered in the context of the risky measurement of society. “Black Swans” – events that have extremely low predictability, in terms of their impact, can dramatically transform the world. Today, the society is filled with extremely unpredictable events, which make its development as vague as possible. Existing systems of rational analysis, and as a consequence, control, can not see the “invisible” – the “Black Swans”, whose appearance drastically changes the course of events. One of the key reasons is the lack of desire for a systematic vision of processes and phenomena, trust in fact, and not in essence. The perception of social reality is dependent on a knowledge order: education, the sciences, the media, but at the core – the characteristics of human nature in its relation to the accidental, uncertain. The architecture of modern society can generate “black-whitewashed” events, but also, being a risky society, develops strategies for adapting to them, taking into account their not only negative, but also positive potential. Such accidents as black swans provoke both hyperconservatism and hyperventurism, and between them there is a diversity of forms of being of the multidimensional man of a risky society who must reject patterning in thinking.