The paper focuses on the analysis of phenomena involving the individual’s handling of difficult life situations (DLS). Handling DLS is interpreted in the context of ‘three cultures’: in the interrelation of the culture of scientific knowledge, the “ideofield of culture” and the culture of individual experience. Existing theories of individual response to difficult situations are analyzed; it is shown that the methodological core of most concepts is the ‘postulate of conformity’ (‘adaptability’) when interpreting human behavior. Along with the well-known ‘defensive’ and ‘coping’ behaviors that are adaptive in nature, non-adaptive forms are distinguished (‘self-destruction’ and ‘mastering’), and a two-dimensional typology of addressing DLS is proposed based on the distinction between ‘activity/passivity’ and ‘adaptability/non-adaptability’. Self-destruction is characterized as passive non-adaptive behavior (disadaptation); ‘defense’ means passive adaptive behavior (actually, adaptation to the situation); coping is active adaptive behavior (overcoming the situation); and mastering is active non-adaptive behavior (overcoming difficulties). Three ways of mastering are described: post-factum simulation of situations; a testing of the individual’s capabilities in a previously unknown situation (‘emotional flutter’); and ‘emergency simulation for future use’. The ways to reflect upon the person’s own behavior in a DLS are also considered to transform the two-dimensional model into a three-dimensional one to reveal the attitude of an individual to difficult life situations. It is demonstrated that in the subjective plane (the semantic aspect of self-reflection) a picture of the methods used to handle a DLS that is ‘drawn’ by an individual may significantly differ from the objective picture of what is happening (that is established according to the criteria of scientific knowledge). This paper presents a model of the personological synthesis of the three cultures for interpreting and correlating the forms of the person’s handling DLS. In this context, some techniques are described that enable the co-organization of individual experience, elements of the ‘ideofield of culture’ and scientific knowledge to contribute to altering the individual’s attitude to difficult life situations and increasing the meaningfulness of their personal behavior.