Abstract: The distinction between naive and sentimental poetry had ever inspired Jung’s psychological view on introversion and extroversion, then Jung interpreted Schiller’s aesthetic education thoughts from the perspective of “introverted thinking type”. Jung highly appreciated Schiller’s insistence on person, since the perfection of person were both the ultimate goal of aesthetic education and psychology therapy. However, Schiller’s comprehension on person mainly based on the constructing will of transcendental subject, and his aesthetic reconciliation mainly based on rational subject’s autonomy, thereafter, the symbolic potential of gods image were deprived by aesthetic ideal. Jung’s emphasis on the symbolic origin of idea led him to regard resurrection of gods image as a natural psychological process, which paralleled to the individual’s combination with one’s inner self. This paper will discuss Jung’s interpretation and diagnosing on Schiller’s aesthetic thoughts, and aims to illustrate the personification dynamic process of aesthetic education from the perspective of subjective transformation, which not only parallels to the individualization process of analytic psychology, but also is the foundation of the wholeness of cultural order. Besides, the personification process also provides us with a critical reflection on the legitimacy of the enlightenment subject.