In our philosophical exploration we shall originally analyze dialectical contradictions of predispositions and skills as a source of memory phenomenon development; the patterns leading to the human professional activity evolution, as well as the identification of obstacles and barriers. The area of human orientation in the world of changing opportunities under the influence of the information society formation, hyper-reality and Smart Society in the cognitive innovation perspective, which is defined in the twenty-first century in the novelties of the labor market, new professions, in the processes of technological development, digitization, and transition to the virtual world of communication networks and the Internet, is justified. Moreover, studies of the memory environment reveal a search for "a certain space of inclination," as well as "corresponding features of each block" of the memory environment, determining the patterns of individual professional selection and prospects of a figure, as the subject not only of professional activity in particular, but of life in general. The correlation of the activity approach developments within the development of the subject’s life as well as the model of predisposition realization by M. Achtnich mentioned as holistic and optimal one, maintained by the specific-historical conditions of the figure, have mostly determined the key problem, which this article is devoted to. The purpose of this scientific exploration is the philosophical understanding of predisposition and skill dialectic in human professional activity (on the example of models by Martin Achtnich and Gregory Popov). The achievements of the theoretical model of Gregory Popov represent the significant results of the solution of the issue, to which P. Drucker reached himself in his formulation of "Smart Approach." It is the aforementioned concept that stands now decisive for the prospects of a "smart society" dispute in various activity spheres. Furthermore, the following disposition considers the praxeological perspective of knowledge of the patterns of the "inclination-skills" contradiction resolving application based on the models of G. Popov and P. Druker.