The article presents results of an empiric research of the psychological content of difficult real-life situations and ways of overcoming them from the position of modern school children. Constructive and non-constructive ways of overcoming life difficulties are singled out; the article also discusses age-related and individual specific behavior of teenagers in difficult situations. The study of content characteristics of difficult life situations and ways of overcoming them was carried out in general educational schools of Ulyanovsk in proportional selections (n = 178 school children of different age groups – junior group (10–11 y.o.), senior group (13–14 y.o.), and teenage group (15–17 y.o.). Application of psycho-diagnostic tools, such as dialogue, frustration test of S. Rosenzweig, helped to single out social and age-related peculiarities of the content of difficult real-life situations and the ways of overcoming them. The results showed that the level of constructiveness in overcoming difficult life situations has an irregular pattern – the constructiveness level increases at the age of the 13 and decreases at the age of 15. Young adults and teenagers perceive and evaluate their behavior as constructive anyway. The data regarding types, subject, and ways of overcoming life difficulties in school children belonging to 3 age groups can be used as a foundation for school psychological activity that will help school children to behave constructively in case of difficult life situations.