“The Moon and Sixpence” is one of the most important novels of Maugham, laying the foundation of his early reputation. This novel is a representative work reflecting the spiritual world of Western dreamers in the 20th century. It mainly explores the contradiction and interaction between life and art, and deeply reflects the social condition of Western capitalist countries, where people have abundant material but are spiritually barren in the late 19th and early 20th centuries. In this paper, the methods of textual analysis, generalization, and summarization are employed to discuss the psychological view of Strickland on his way to self-redemption under the Hierarchy of Needs Theory. It is his gratification of the “deficiency needs” and the emergence of the highest needs—self-actualization that makes him escape from reality and decide to pursue art. After analyzing his motivation, this paper explores the internal and external obstacles on his way to self-redemption through analyzing his psychology and the background at that time. Finally, it is found that his self-redemption is achieved by returning to nature and resorting to art, which can bring a guidance for the confused later generation on spiritual redemption. Also, through the process of analysis on Strickland under the Hierarchy of Needs Theory, the practical value of Maslow’s theory can be further confirmed, and the understanding of the character of Strickland can be broadened from another perspective.