The notion of the “Self” is one of the most critical issues in contemporary cognitive science. Whether the self is a single and independent real entity or a collection of constantly changing experiences has been at the core of debates between the substance theory and the illusion theory. Compared to the neglect of this issue in Western tradition studies, the meticulous practice of mindfulness/awareness in Eastern research traditions has long focused on this contradiction. This paper navigates the intricate dimensions of the “Self” by weaving together the Oriental framework of the five aggregates with the Middle Way, the principles of constructivism, and the empirical methodologies of experimental philosophy. This approach bridges the gap by synthesizing introspective first-person experiences with objective third-person scientific observations to enrich the understanding of self-constructivism. The implications of these findings extend into the practical realms of psychology and philosophy, offering a scaffold for future research to elucidate the multifaceted nature of the self further.