In the beginning of Analects, Zi Lu sat beside Confucius and kept records as he asked his disciples about their ambitions. Zi Lu's ambition was to make the people bold and make them understand righteousness; Ran You's ambition was to provide plenty so that the people could live comfortably; Gong Xi Hua's ambition was to be a moderator; Zeng Dian's ambition was to bathe in the Yi River, enjoy the breeze among the rain altars, and return home singing. After hearing this, Confucius sighed and gave his approval to Zeng Dian. Why did Confucius approve of his ambitions? Each scholar gives their own explanation. This study analyzes the opinions of 37 commentators, compiling twelve commentaries into four categories. In order of appearance, the first commentaries are on understanding the world and reveling in preaching, the second commentaries are on heavenly principles, the third commentaries are on traveling the world, and the fourth commentaries are on rain sacrifices and the code of ethics. There are large differences between these four categories. Understanding the world and reveling in preaching were proposed by He Yan, which denoted that Zeng Dian was familiar with the state of the world, was unwilling to serve as an official in those chaotic times, and lived his life freely. The heavenly principles and humanly desires and sagely astrology were later written by Zhu Xi, which stated Zeng Dian's ambitions were above those of Zi Lu and the rest and elevated him to a lofty level. Huang Zhen put forth consideration about the commentaries on traveling the world, in which Confucius experienced world's chaos and heard Zeng Dian's idea unexpectedly. This stirred his thoughts of traveling abroad which caused him to sigh in grief. Rain sacrifices and the code of ethics were raised by Wang Chong, which were reinterpretated by the Qing Dynasty commentators. These mentioned Zeng Dian's code of ethics and harmony which sought to reform people from within and was separate from the methods used by Zi Lu and the others. These four types of commentaries each quote the classics; the author followed the order of their appearance to describe the process by which they were created. Then Kuhn's paradigm shift was used to explain the paradigm shifts that occurred during the creation of these commentaries.