The relationship between education and entrepreneurship is a pressing need in the contemporary world and is increasingly present in educational agendas at a global level. With the emergence of the OnLIFE Education paradigm, which refers to an education connected to life, resulting from the hybridization of the biological world, the physical world and the digital world, it is increasingly urgent to rethink the current epistemologies and theories, which are unable to encompass the complexity of this paradigm, since they limit action only to humans, in an anthropocentric view of the world that is evidenced, above all, by instrumentalist approaches that do not consider ecosystemic relationships, made possible by the connective act. In this context, the main objective of this research is to analyze how the OnLIFE Education paradigm problematizes and reconfigures the relationships between education and entrepreneurship, based on well-founded practices that can contribute to the emergence of a new conceptual elaboration. In order to achieve the proposed objective, the research is developed based on the cartographic method of intervention research through three interconnected territories. The first refers to the literature review, the second to the theoretical intercessors, and the third to the devices. The research is based on the analysis of the emerging concepts from the literature review on education and entrepreneurship, as well as entrepreneurial skills, and investigates how the theoretical-practical devices—TARDIS Mission and Feline Project—challenge the established traditional concepts. The results of this triangulation have allowed us to understand the urgency of developing more disruptive educational approaches based on the concept of OnLIFE Entrepreneurial Education, which necessarily implies a profound transformation in the cognitive regime that guides education at different levels and contexts, since it proposes working with the problematization of the world, invested with a transubstantiated entrepreneurial attitude that permeates the different domains that constitute OnLIFE.