Egon Schiele (1890–1918) is one of the most significant representatives of Austrian expressionism, whose works influenced not only numerous painters and graphic artists, but dancers and theatrical stage employees as well. However, few academic publications are devoted to E. Schiele’s creative work, and among the existing ones, there is a significant proportion of those where his paintings are considered as the evidence of deviations in the painter’s mental health. The main method used in the present work is the philosophical and art studies analysis, appealing to the universal meanings of works of art. Three paintings: Self-Portrait with Black Vase (1911), The Holy Family (1913) and Death and the Maiden (1915), which can be combined into one series demonstrating the genesis of Egon Schiele’s ideas about art in general and about his creative work in particular, are the material for this study.