This article focuses on the importance of reflective experiences in education. It firstly reviews and compares the Humboldtian Bildung and the Kyoto School, represented by Nishida Kitaro. Both philosophies emphasize the importance of reflective experiences in education, criticising the specific knowledge-skill-based instruction approach. In this sense, the two views are similar. However, this article further explains the significant difference in how the self is considered in relation to the world within each thought, and therefore, how each educational approach is different, namely as seen in the idea of negative education from the Kyoto School. In the latter section, this article develops the discussion of reflection in the process of learning provided in the OECD Education 2030 framework, which was initiated in 2015 and that is still ongoing. Criticising didactic learning as the sole approach for knowledge and skill acquisition, the OECD Education framework advocates instead for the importance of student self-reflection in relation to society to support a broader development of necessary competencies. By comparing the two schools of thought, the article reveals the underlying assumption of self in Western mainstream educational philosophy, and it argues for the importance of open-mindedness toward the other worldview.