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The study investigates two educators’ critical reflections on their transformative multicultural experiences, wrestling with the Chinese traditional virtue of modesty that emerged from Taoism. This study draws the original concept of humility in education from Ch’ien hexagram of I-Ching and chapter 8 of Tao Te Ching. Mezirow’s transformative learning theory is adopted to explore the intersectionality of multiple identities and further negotiate the meaning-making processes through critical reflections and dialogues. Reflecting on primary and secondary literature on these two Chinese classics, this study engaged in a critical philosophical inquiry to scrutinize their teaching practices through reflections, journals, and conversations. Findings revealed that both authors extended their teaching practices by cultivating modesty and cultural humility in the international higher education landscape.