The article is concerned with the cognitive aspect of the entrepreneurial mindset when teaching entrepreneurship. To encounter the escalating complexity underlying the discipline of entrepreneurship, the Hegelian dialectical method is applied to the conceptual pillars of Shane’s individual-opportunity nexus: opportunity and knowledge. Step by step Hegelian sublations in each dimension lead the concepts to their opposites and ultimate synthesis in an integrated dialectical framework. Opportunity is contrasted with support and knowledge with ability. The dialectical tensions reveal the dynamic emergence of entrepreneuring by unifying the contrasting concepts into the entrepreneuring milieu and the entrepreneuring competence. Pairs of opposing concepts from each dimension reveal four complementary entrepreneurial styles. The emerging typology introduces new, inherent, and spontaneous conceptualizations of the plethora of entrepreneurial factors that individuals perceive as critical to success. Implications of the dialectical method pertain to reconceptualizing the relationships among fundamental entrepreneurial notions while teaching entrepreneurship to diverse audiences. The present approach delves into the promising philosophical underpinnings of dialectics with a potential to develop a new tool in educational practice.
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