This book aims to bring pedagogy into dialogue with the current challenges of future sustainability. The reflections are developed as a dialogue within a shared framework aimed at keeping alive the urgency to question the meaning of education. Consequently, the intention is to address the issues that most characterise the peculiarities of the educational professions, in particular that of the adult teacher-guide in his-her relationship with the child, representative of an education to life, for life and through life, in the plurality and complexity of its dimensions. In the first part, Rita Casadei reflects on the dual role of education, in its being both objective and resource of transformation and for the recovery of an ecological, eco-systemic, profoundly human and unreserved awareness. In the second part, Italian and Japanese researchers discuss the topic, according to their professional experience, cultural sensitivity, theoretical conviction and interpretation. The emphasis on dialogue stems from the awareness that on education, as on life, a definitional and definitive discourse is inadequate.