The book starts with a description of the vinegar tasters, which is a painting portraying the three great eastern thinkers, Confucius, the Buddha, and Laozi over a vat of vinegar. Each tasting the vinegar of "life," Confucius finds it sour, the Buddha finds it bitter, but Laozi, the traditional founder of Taoism, finds it satisfying. Then the story unfolds backing up this analogy.
Hoff presents Winnie-the-Pooh and related others from A. A. Milne's stories as characters that interact with him while he writes The Tao of Pooh, but also quotes excerpts of their tales from Milne's actual books Winnie-the-Pooh and The House at Pooh Corner, in order to exemplify his points to the reader and the characters. Hoff uses many of Milne's characters to symbolize ideas that differ from or accentuate Taoist tenets. Winnie-the-Pooh himself, for example, personifies the principles of wu wei, the Taoist concept of "effortless doing," and pu, the concept of being open to, but unburdened by, experience, and it is also a metaphor for natural human nature. In contrast, characters like Owl and Rabbit over-complicate problems, often over-thinking to the point of confusion, and Eeyore pessimistically complains and frets about existence, unable to just be. Hoff regards Pooh's simpleminded nature, unsophisticated worldview and instinctive problem-solving methods as conveniently representative of the Taoist philosophical foundation. The book also incorporates translated excerpts from various prominent Taoist texts, from authors such as Laozi and Zhuang Zhou. However, one poem included in the book attributed to Lu Yu of the Tang Dynasty was actually written by Song Dynasty poet Lu You.
