After a philosophical presentation of security as a property of being, its origin, structure, functioning and future, as stemming from the Initial Conditions of the Universe (mass, energy, space, and time), from the primary identified by Aristotle (material, effective, formal and teleological), and from the elements of the system distinguished by social cybernetics (sociomass, socioenergy, sociostructure and socioculture),the author attempts to argue that the pillars of a holistically analyzed security are: (1) Procreation and Education; (2) Affluence and Welfare; (3) Law and System; (4) Freedom, Equality, Fraternity and Responsibility. At the same time, the author asserts, invoking Aristotle, that the methods and ways of shaping those pillars and thus security are: necessary things (war and work) and beneficial things (peace and rest). The author tries to analyze those things and the holistically understood pillars of subjective security by differentiating such fundamental spheres of subjective security as the demographic, economic, political-social and cultural-civilizational spheres. Relations between subjective security (its pillars) and objective security (its spheres, tools and instruments), are presented as atendency that appears in the research of the so-called Kopenhagen School with the intent to deepen (subjective) security, expand (objective) security and thicken security (preferences for certain subjective-objective relations). Accepting the division of security into, on the one hand, positive security identified rather with the so-called nonmilitary security, following Johan Galtung (security through work, peace and renouncement of violence), and, on the other hand, negative security often identified with military security (security through war, destruction and violence), the author focuses on relatively evaluated security (in relation to somebody or something). This relative evaluation of security is analyzed in the perspective of the deepening and thickening of the transregional security of Poland, after several critical remarks about the understanding of such security and the so-called regional and transregional security complexes. The author assumes that, among the pillars, elements, sectors and complexes of security, the most dynamic and binding seems to be the demographic and economic sphere, whereas the political (legal-systemic) sphere and the cultural sphere belong, in comparison, to the more static (less dynamic) ones. Invoking J.J. Rousseau’s distinctionspertaining to this sphere (among others, the distinction between small, medium-size and big states), the author hypothetically concludes that Poland already was a big and monarchic state at the time of the First Commonwealth, a medium-size state at the time of the Second Republic and maybe also the Third Republic, and that Poland has a future as a small state composed of city-states (as anticipated by A. Toffler) of a democratic and perhaps a deliberative model (promoted by, among other, J. Habermas) – a structure of citizens competently communicated with each other, more democratic than any structure known from today, and also assisted by Artificial Intelligence.