In cultivating a Western inclination toward Eastern wisdom, it is important to seek the foundations that sustain traditional practices toward such end. In a secularised and modern world view, the tendency has been to extract and abstract foundational practices such as mindfulness meditation and contemplation within an objectivist or scientistic prejudice. While leading to interesting results, it cannot ascertain a wisdom that is quantified and decontextualised. In response, contextual effort in postmodern pedagogical literature—while well placed—is often marred with confusions concerning Eastern and metaphysical foundations. As a result, one is led away from the very wisdom being qualified; furthermore, conceptual and theoretical paradoxes arise and consequently elude those that formulate them. Thus, in feeling secure in response to a particular ‘yáng’ world view of modernity, many postmodern criticisms suffer an exclusively ‘yῑn’ character. For us, imbalance in any direction forfeits the path Eastern education approaches wisdom. In our conceptual analysis, we contextualise that modernity was never too yáng, but too yáng-in-yῑn. Therefore, what is missing in pedagogical theory is not the yῑn element, as presumed by postmodern critique, but the yáng element, in continual balance with the yῑn, and vice versa.