As might be expected, a degree of comparison has also been explored between Winnie-the-Pooh's companions and the enneagram (Kendra Jernejcic, The Enneagram in the Hundred Acre Wood, 10 September 2018; The Enneagram According to Pooh, The Enneagram in Business, 23 December 2009; The Enneagram as Explained by Winnie-the-Pooh, Reddit, 2018). Aug 14, 2014 · The way I will present the personality types is with the Merrill-Wilson breakdown. There is also Meyers-Briggs (more complex) and the classic Four Temperaments. The Merrill-Wilson has the best ROI. Simple to understand and identify fast. The four personality types are: Driver, Expressive, Amiable, and Analytical. Eeyore is usually described as having a depressive personality and in the first book that is mostly true. Later on, however, his gloomy outlook becomes more revelatory. He is depressed because he looks around him and see he is surrounding by idiots. Nice, loyal, friendly, supportive idiots, sure, but idiots nevertheless.