Will my children's creativity be hindered if I place them within the rigidity of an East Asian school? Conversely, could my children's math and science skills benefit from the high expectations of an East Asian curriculum and teacher? The purpose of this study is two-fold. Firstly, it aims to demonstrate that comparison between Eastern and Western educational traditions can be framed in terms of a dialectic concerning students' development, autonomy, learning environment, and curricula. Secondly, it is to analyze the substance and effects of this dialectic in the context of 15 families of mixed educational background situated between Eastern and Western educational traditions. These families in Hong Kong have access to educational opportunities for their children in adherence to educational styles associated with either Eastern or Western culture, or a combination of both. This study seeks to illuminate the possible dominance, abandonment, and/or synthesis of cultural background when evaluating schooling options for children in families of mixed educational background. The study finds that these families largely inclined towards educational ideals more associated with Eastern characterizations while their children were at the primary level of education. In stark contrast, they unanimously favored Western propensities in education when their children were in secondary school and beyond. This study concludes that there may be wider ramifications of this model of intercultural compromise beyond the level of the intercultural family, particularly as it relates to broader global and comparative educational discourse surrounding notions of how creativity and innovation may be fostered in culturally defined educational contexts. A bibliography is included.