What is the essence of Chinese Calligraphy? It is the most important and difficult question in the history of Chinese Calligraphy art. The explorations that ancient Chinese artists had made on this question can be classified into three main schools: the first school emphasizes the objective manifestation form, which is represented by Cai Yong’s doctrine, “Calligraphy originates in the nature”, and also is represented by Kang Youwei’s “Calligraphy form theory”; the second school emphasizes the subjective information intention, which is represented by Yang Xiong’s doctrine, “Calligraphy, the drawing of mind”; the third school emphasizes the combination of subjectivity and objectivity, which is represented by Liu Xizai’s “theory of meaning and image.” In my opinion, it is necessary to combine the subjectivity and objectivity when we want to understand the essence of Chinese calligraphy. To understand it, however, we cannot just depend on the ways, like savvy, metaphor and analogy, which are treated as Chinese philosophical methodology. We need to analyze the dialectical unification relationship in mind-form and meaning-image under the system of speculative philosophy, which means we have to use the logical thoughts in western philosophy. It is just that the traditional western philosophy cannot provide a reasonable explanation to the essence of Chinese Calligraphy, due to its dualism worldview of subject-object separation. But the information philosophy in contemporary China, which is built on the basis of criticizing such traditional dualism, can afford an explicit and systematic explanation to the essence of Chinese Calligraphy, and no matter the subjective mind and meaning or the objective form and image can be dialectically unified on the basis of information mediums.