One of the necessary discussions of educational sciences, especially of the philosophy of education, is to present a critical knowledge of the schools of education, with a comparative study of these schools and some contemporary religious philosophical schools. This research tries to criticize Tao’s aims and educational principles, based on the transcendental wisdom of Molla Sadra, to achieve this goal. Using an inferential method, I have first extracted the goals, principles and educational methods of Taoism; and second, I have criticized Taoism and its philosophical foundations based on the transcendental wisdom. The most important educational goal of Taoism, as I have researched, is educating human in harmony with the true tariqa (method), i.e. Tao. Examining these goals and principles on the basis of the transcendental wisdom, I will show that the lack of proper theology and the philosophical gap between ontology and anthropology has made Taoism - as an educational philosophy - incapable of correctly interpreting its goals and principles - such as balance and complete obedience of tariqa - in the first place. Nevertheless, some of the educational teachings of Taoism, such as simplicity, return to nature and balance between physical and mental education, can have a positive messages for education and training.