In this essay, the author provides a working definition of philosophy from a cultural point of view, and argues the need for mathematics educators to develop their philosophy of mathematics teaching and learning or, to speak more broadly, their philosophy of education. He then historically situates three scholars—John Dewey, Paulo Freire, and Michel Foucault—who have been instrumental in the formulation of his philosophy of education. Next, he shares how the philosophies of these three scholars provide different languages to critique three aspects of education. He concludes with brief discussions on the process of his ever-evolving philosophy of mathematics teaching and learning and the emerging debates about the “grand challenges” for mathematics education.