The aim of this paper is to examine the relationship between education and technological rationality from the perspective of the philosophy of education, and to show that while education is deeply related to technique, skills, or technology, it can never be reduced to technical knowledge, and that there are things in education that overflow technical knowledge. I will here ask why there is something in education that overflows technical knowledge -- I will define it as "knowledge of pathos" -- and why it is necessary to redefine the meaning of education in terms of knowledge of pathos. In order to address this issue, I will first examine the relationship between technology and transcendence in the world of education in Kei Hachiya's "Education and Transcendence." Second, I will show that recent outstanding theoretical achievements of Japanese philosophers of education -- Satoji Yano's "Education from the Perspectives of Gift and Exchange," Yasuo Imai's "Medial Perspective on Education," and Tsunemi Tanaka's "Clinical Theory of Human Becoming" -- are all located within the problematic area of 'technology-pathos-education'. Finally, I would like to propose a 'philosophy of education built on fragile parts', with a view to redefining education through the knowledge of pathos, paying attention to the experience of "pathei mathos" and the opportunity of weakness in the philosophy of education.