The complexity of issues related to entrepreneurial activity is reflected in the discourse in the world of economic sciences that has been continuing for over 200 years. Nowadays, the development of organizational management environment is more and more extensive and, as well as in other highly developed countries, the sector of small and medium-sized enterprises in Poland plays a fundamental role in the economy. Yet, there are rising concerns towards the entrepreneurial education direction in world of science. The growing concern in the context of entrepreneurship education has caused a discourse on whether this scholar activity can affect the entrepreneurial effectiveness in practice. We conclude that the contemporary academic management papers are, in a vast majority, focused on theoretical aspects of entrepreneurship, students, granted programs and trainings, while the opinions of real entrepreneurs toward abovementioned valuable efforts are omitted. Therefore, we decided to explore practical entrepreneurial environment to address this gap. The research participants included 189 entrepreneurs (SMEs based) that had been operating continuously for minimum 20 years. We established three objectives of this paper: to analyze the relation between the individual level of education, its characteristics and entrepreneurial success; to evaluate the state educational support in real world entrepreneurial operations effectiveness; to identify educational opportunities and threats and estimate the future research trajectories in this area. Finally, the first attempt, in the world of science, was undertaken to verify whether there is a positive correlation between entrepreneurship teaching and its real effect on entrepreneurship in practice. We empirically prove that the (higher) education can be an obstacle on the path of entrepreneurial success. Additionally, conclusions establish a new perspective on the existing state of knowledge through constructing a bridge which will enable connecting academic efforts and expectations on the part of firm owners.