Abstract: Following his demotion to Huangzhou in 1081, the fourth year of the Yuanfeng era in the Northern Song dynasty, Su Shi experienced a profound shift in his worldview. During this period, he began writing a series of essays capturing his diverse thoughts and observations. These writings were later compiled posthumously into the five-volume Random Jottings of Dongpo. The collection conveys Su Shi's deep understanding of human nature, his philosophical outlook on life, his acceptance of fate, his insights into health and well-being, and his retrospective critiques of historical figures. Random Jottings of Dongpo offers a window into Su Shi's genuine character and life philosophy, encapsulating his nuanced and thoughtful reflections on life. Its enduring relevance invites fresh interpretation and analysis.