Dong Qichang is one of the central figures in the history of calligraphy, painting and theory of art of the Ming Dynasty period (1368–1644). Dong Qichang's art gave rise to a separate movement known as Songjiang Pai that strongly influenced the visual arts of the XVII–XVIII centuries. Dong Qichang’s life was focused on two ambitious goals: taking the post of the empire’s high-ranking dignitary and becoming the first calligrapher and painter of his era. Dong Qichang's biography is unique in that he succeeded in achieving both goals, for he saw no contradictions between the two. Art critics consider Dong Qichang's art separately from his career path. The purpose of this study is to understand which aspects of traditional calligraphic aesthetics and Dong Qichang's own views allowed him throughout his life to successfully combine his work with the time-consuming career as an official. The study subject is Dong Qichang's album known as “Own Uncial Transcription of Imperial Decrees on Appointments to Public Positions” from the Shanghai Museum Collection. In his art, Dong Qichang aspired to the ideal of "naturalness of celestial reality" combined with the requirement for constant hand movement control that provided a healing effect of the creative process on the author's psychosomatic state. Dong Qichang regularly presented his works to influential people at court, cultivating the right connections for career purposes. Creativity allowed Dong Qichang to cope with temptations and risks of the high social status. Art elevated Dong Qichang over the harsh social realities, without disengaging him from them. The path of solitary seclusion was not something that appealed to Dong Qichang; instead, he was inspired by examples of socially active calligraphers and painters of the past. It is natural, therefore, that Dong Qichang's life and creative experience continue to be relevant for many artistically gifted businessmen and politicians of modern China.