During the middle to late periods of the Ming Dynasty, the commercial economy experienced striking development, yet political corruption and congestion of the imperial civil service examination system deprived many scholars of a pathway for elevation. Many people therefore opened up new avenues, preparing for the examinations while simultaneously exploring different ways of life, expanding new fields of activity so as to realize value in life. Zhang Dai 張岱, who originated from a great clan in Shaoxing, was one such person. Whilst reading, assembling scholars, critiquing theater, and engaging in other activities, he gradually created considerable renown and achievements for himself. In reviewing Zhang Dai’s life, his inability to enact change in the face of the incoherent society of the late Ming Dynasty was the first great tragedy of his life. He endured by leading a life of pleasure, realizing his ambition of accomplishing great things in a roundabout fashion. After the fall of the Ming Dynasty, he experienced the second tragedy in his life, which caused him to nostalgically ponder the events of the past and, in his extreme grief, he resorted to the writing brush to express his thoughts and emotions, including writing history to pass on what was left of his life. Throughout his life, Zhang Dai produced many written works, perennially relying upon his writing to make a living, and leisure, extravagance, comfort, sorrow, lamentations and grief for the world all became subjects of his writing, ultimately allowing him to find a different path in life and achieve longevity in academic and cultural history.