Changes in the line of the development of the culture of contemporary society, which until recently stayed within a common mainstream globalization trend, have exacerbated the issue of changing the paradigm in urban approaches in the era of postmodernism. The involvement of axiology tools in the discussion of architects, city-planning councils, and investors about finding new horizons for high-rise construction is quite timely. The system-structural method, as well as the method of philosophical interpretation, made it possible to formulate the problem of finding analogies in the interpretation of the phenomenon of a skyscraper. The objective of this paper was to study a skyscraper as a special cultural phenomenon, symbolizing the strive for power. The implicitness of the hermeneutics allowed us to articulate new meanings in the modern perspective of the skyscraper phenomenon. It has been established that, as a symbol of power and cultural leadership, the architecture of a skyscraper, while maintaining its relative independence from the cultural landscape, affect the infrastructure of urban space and represents globalization processes in the contemporary cultural environment. This study used a feature of the metaxological method, which captures new meanings in the dialectical flow of choice. Thus, realization of the consequences of the connotation “height is the power over nature” can discover new axiological tools and, with a holistic approach, correct the imbalance in terms of the prospects for high-rise construction.