The rupture of metaphysics not only showed the limits of modernity and its educational project, but also put into question Western thought itself, in its structure, generating estheticist relativism, and at the same time, enabling the emergence of diversity. What, then, are the prospects for new ways of understanding and transcending the self and knowledge of the modern educational project, amidst the challenges of contemporary education? Faced with this challenge, this paper, in the horizon of the dialog between the Complex Thought of Edgar Morin and the Philosophical Hermeneutics of Hans-Georg Gadamer, aimed at educational proposals seen beyond the dualism, in the scope of the Hermeneutic Complexity. A dialog was carried out between these proposals, given their importance among the themes of reflection in education: the first, because it signifies a production from the natural sciences, and the second, a production from the sciences of the spirit. Both proposals are proposed beyond the modern purposes, both regarding science and education. Each, in its way, presents structures and reflections that, when interwoven, can enhance references to the challenges of the fragmentation between matter and spirit, natural and human sciences, and linear and homogenizing processes in education, enabling us to understand humans as historical modes of being.