With the opening of Chiang Kai-shek's diary and publication of related materials such as President Chiang Kai-shek's Five Records (Jiang Zhongzheng zongtong wuji), we are amply helped to understand the details of his private life and its relations to his public behavior. This paper uses ”Xingkeji” (the Record of Self-Reflection and Self-Control) in the ”Wuji” as the major source for analyzing the origins of his xingke ideas and practices. Chiang's notion of xingke was based on two foundations: his Neo-Confucianism and his Christian background. Under the influences of Neo-Confucian self-cultivation and Christian introspection, Chiang examined his moral flaws and other serious malpractices. He adopted a traditional Chinese way of correcting oneself known as ”the evaluation of merits and demerits”(gongguoge). Besides, he also developed and used persistently a meticulous and effective mnemonics to remind himself of lessons of failure for self-improvement. Furthermore, Chiang's xingke included the dreams that he had as reflections of his daily expectations and fears. All of these practices reveal very probably that he was quite an introspective, moral, and responsible person. These traits and practices seemingly aided his career. After 1949, as President, his character also had a deep influence on the Republic of China in Taiwan, as be added ”ethics” to the twin objectives of ”democracy and science” as advocated by May Fourth scholars as the most basic principles to construct a modern Chinese state.