The article deals with the analysis of situations of uncertainty in various spheres of modern society life which have arisen as a result of the rapid development of digital technologies; virtualization of many components of modern human life; the increasing role of visual information in communication; drastic changes in the labor market, in intellectual practices and the formation of new requirements for the education and vocational training system. We have proposed to analyze such situations using the principle of "incomplete comprehension of the object", and we carried out a consideration of its content and indicated its methodological role. To our mind, one of the most important features of this principle is the focus on a set of ambiguous, non-obvious links between the internal elements of an object, as well as while its interactions with agents of external influence in a situation of uncertainty. Besides, we examined its heuristic and predictive capabilities using examples of analysis of specific typical situations in various spheres of social life, primarily related to the labor market and education in a digital culture.