Purpose This study re-examines the relationship between jiao (lit. teaching) and xue (lit. learning)—the foundational education concepts in the traditional Chinese cultural context—to enlighten our contemporary understandings of education and educational research. Design/Approach/Methods This study first lays its foundation on an etymological investigation. It then integrates two mutually connected approaches— the classics and the self as method—to present a comprehensive analysis. Finally, it critically reviews the methodology used in this study. Findings The interdependency of xue and jiao has an etymological foundation, supported by canonical doctrines and verified by individualized experiences. The interpretation of xue as xiao (to imitate) describes the origin and process of education in which the junior imitated and followed the elder, while the extended interpretation of xue as jue (to awaken) stresses the effects and functions of education. In the classical Chinese context, greater significance was placed on xue—the keyword concurrently connoting the meaning of teaching and learning in the modern sense. It is misleading to narrowly render the originally meaningful word group xuexi as learning in modern English. Originality/Value This study consults sources in multiple languages and integrates both the classics and the self as method. Based on this, the etymological investigation, canonical analysis, and experiential reflection are collated to provide a rich and deep discussion. By focusing on the core characteristics and the concepts they imply, this study also touches on the key characteristics of the hieroglyphic system and the unique way of thinking it represents.