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The declaration of dependence and subordination in a hierarchical relationship can be an adequate individual response to today's social challenges. The study seeks to answer the question why someone chooses a less independent situation compared to their current state and within what model framework such choices can be examined. In this context, it is important to distinguish between the concepts of dependence and freedom. According to the study’s proposal Amartya Sen's concept of freedom, which also includes positive freedoms, is a suitable conceptual framework for analysing such decisions. Of the positive freedoms, security is particularly important. The paper will explore this issue on the basis of Zsuzsa Ferge's writings. Three specific examples (freedom and security in postsocialist Hungary, public sector employment, and Southeast Asian peasant farms living on the edge of subsistence) illustrate that, by choosing Sen's extended concept of freedom as a framework for analysis, Kahneman and Tversky's prospect theory can be an adequate tool for the formalised study of the trade-offs between different types of freedom.