The purpose of this paper is to find how Washington could succeed as a great leader even though he had no land ownership and educational background, which served as a success factor in the Virginia society in the 18th century. Washington has persistently pursued a path to becoming a successful gentry in the Virginia community and, to this end, he constantly pursued learning through reading to gain the knowledge. The first path Washington chose was a path of self-development to thoroughly become like his older brother. Washington had his brother Lawrence and his brother’s father-in-law Fairfax as his mentors and absorbed their teachings like an absorbent sponge. Washington was certified as an independent surveyor and worked as a full-time surveyor. And he bought his own land with the money he earned as a surveyor. He volunteered for the Virginia militia, became an officer like his brother, and even advanced to the colonel. Washington did his best to become, like his brother, a successful gentry, a successful soldier, a successful politician, and to be recognized by the United Kingdom. Washington s second choice was reading. For Washington, reading was not far from self-development, but closely related. Washington filled up his lack of education through reading. He bought and read books to be successful as a surveyor, to become a successful soldier, to become the best gentry of farming, to become a successful politician who cares for the community and other inhabitants, and to become a president who makes people in his country happy. Washington read not only the books necessary for farming and military life, but also humanities books such as literature, history, and philosophy that enable people to understand humans and nature. Washington was, through self-development in a competitive society, a successful soldier, a gentry, a politician, but he did not become such a person who abused money and power. Perhaps it is because Washington used reading as a best tool to cleanse humans while developing himself. I think it is because of his reading that Washington, with the greatest strength, went the path of a humble and classy great leader, abandoning the violent savagery dominated by money and power. He could become king or emperor as long as he wanted at that time. However, he became a leader of a finite republic, possibly influenced by the power of reading he constantly pursued until his death.