The focus of this research are the ways of conceptualizing the phenomenon of social entrepreneurship, which in transitional and developed capitalist societies alike, rely on cognitive models shaped by divergent cultural and socio-political contexts. To be more specific, these cognitive models emerge from different theoretical concepts of social entrepreneurship, as well as from contextually different ways of combining the invariant, structural elements of the concept, both of which are dialectically positioned within the neoliberal capitalism ideology discourse. Within the interaction among the elements constituting the structure of the concept of social entrepreneurship (such as social innovation, civic collectivism, an employment of members of marginalized social groups) and the overall neoliberal ideology discourse, which on its own behalf, operates in accordance with certain logical rules as any other discursive formation does, numerous contradictions and paradoxes emerge. The first chapter of this study critically examines the role of social entrepreneurship within the neoliberal capitalism framework through a comparative analysis with philanthropic endeavors and commercial (traditional, profit-oriented) entrepreneurship, as well as by comparing the diverse ways in which this phenomenon is defined in various socio-political contexts. The process of establishing the social entrepreneurship sector in Serbia, initiated in the post-2008 period reached its normative conclusion with the enactment of a unified law regulating this entrepreneurial activity in 2022. However, it remains incomplete both in terms of the cultural conceptualization of the phenomenon and its practical implementation perspective. This assumption is further examined in the second chapter of this paper in relation to the ideas regarding the social and political cultural heritage legacy, constructed by both policy makers and non-governmental organizations (NGOs) engaged in the social protection system which, on their behalf, during the specified period assume the role of social entrepreneurship promoters and emerge as primary contributors to its development. In the third chapter of this study, an exploration of the conditions and operationalization possibilities of key elements within the social entrepreneurship concept is undertaken. This analysis is illustrated through the services provided to the elderly citizens, which provides a framework for developing the thesis on the incomplete process of establishing the social entrepreneurship sector. Subsequently, the fourth and concluding chapter contextualizes these findings within the processes of constructing social issues pertaining aging and unemployment. In addition to drawing the attention to the distinct characteristics and the potential of social entrepreneurship, this research seeks to initiate a discussion focused on exploring possibilities of overcoming the predominantly constraining conditions and factors that influence the further development of this type of entrepreneurial activity within the transitional Serbian society.