American literature is rich in stories of individualists who succeeded only by their own merits and faced the unknown, unexplored territory also called the frontier. This idea defines the identity of the nation to the point that even long after the literal frontier has been conquered and explored, the American spirit is to find new frontiers. This paper provides a brief sociohistoric overview in order to explain why individualism and self-reliance marked the American identity and what conditions those created in America. It also discusses the problems of society which clashed with those ideals, and thereby created the new moral frontier. The analysis focuses on three works: Walden or, Life in The Woods (1854) and Civil Disobedience (1849) by Henry David Thoreau and Narrative of the Life of Frederick Douglass, an American Slave (1845) by Frederick Douglass, all of which uphold the unadulterated idea of individualism and self-reliance. Whereas Thoreau intended to overcome the materialistic, superficial way of modern life and live only on the factual necessities in order to seek out what makes a happy and fulfilled life, Douglass wanted to overcome the hurdles of his life and the life of all other slaves, which he managed to do through his own hard work and expediency. The paper also provides a comparative analysis and synthesis of Thoreau’s and Douglass’s works and their philosophies and differentiates between two kinds of frontier – the internal, or personal, and the external, or the socio-political one – by analysing how those frontiers are overcome by perseverance.