Lessons from a Donkey #2: Eeyore the Stoic, Part 1
- K.Imray
- May 27
- 4 min read
Updated: Jun 28
The old grey donkey, Eeyore, stood by himself in a thistly corner of the forest, his front feet well apart, his head on one side, and thought about things. Sometimes he thought sadly to himself, “Why?” and sometimes he thought, “Wherefore?” and sometimes he thought, “Inasmuch as which?”—and sometimes he didn’t quite know what he was thinking about. So when Winnie-the-Pooh came stumping along, Eeyore was very glad to be able to stop thinking for a little, in order to say “How do you do?” in a gloomy manner to him.
“And how are you?” said Winnie-the-Pooh.
Eeyore shook his head from side to side. “Not very how,” he said. “I don’t seem to have felt at all how for a long time.”
We first meet Eeyore in this opening passage of “Eeyore Loses a Tail and Pooh Finds One”, the fourth chapter of Winnie the Pooh (Milne 1926). Gloomy is the adjective most used of Eeyore by the books’ narrators and by the other inhabitants of Hundred Acre Woods. He might even (I will admit this much) be gloomy. But it is not a surface-level gloominess that Eeyore offers. His is the gloominess of someone given to deep philosophical thought.
As one ancient philosopher taught, increased knowledge is increased sorrow (Qoh 1:18), but then so too is sorrow better than laughter, “for by sadness of countenance the heart is made glad” (Qoh 7:3). Eeyore’s gloom might be seen as a kind of deep gladness, a serious engagement with the nature of things.
I’m not the only reader to notice Eeyore’s propensity to philosophical wisdom. In Pooh and the Philosophers, John Tyerman Williams (1995, pp. 3, 39) identifies Eeyore as a Stoic. I agree with this assessment. Stoicism, one of the schools of classical philosophy, taught that virtue and wisdom were the highest goods, to be pursued through reason, self-control and harmony with nature. Stoics sought apatheia, freedom from destructive emotions, and believed that living in accordance with nature and virtue would lead to inner peace and tranquillity. They taught that a well-lived life, floourishing or eudaimonia, comes not from pleasure or success, but from living in accord with reason and accepting what lies beyond our control.
Here is an example of Stoic thought from Roman emperor Marcus Aurelius (121-180 CE), who kept a journal of his aphoristic wisdom now known as Meditations (6:13):
How good it is when you have roast meat or suchlike foods before you, to impress on your mind that this is the dead body of a fish, this is the dead body of a bird or pig; and again, that the Falernian wine is the mere juice of grapes, and your purple-edged robe simply the hair of a sheep soaked in shellfish blood. And in sexual intercourse, that it is no more than the friction of a membrane and a spurt of mucus ejected. How good these perceptions are at getting to the heart of the real thing and penetrating through it, so you can see it for what it is.This should be your practice throughout all your life: when things have such a plausible appearance, show them naked, see their shoddiness, strip away their own boastful account of themselves. Vanity is the greatest seducer of reason: when you are most convinced that your work is important, that is when you are most under its spell. See, for example, what Crates says even about Xenocrates.
This blunt stripping-away of illusion is a Stoic habit of mind. The Stoic is to see things as they are. They are not to be seduced by appearances or emotional reactions.
Marcus Aurelius also wrote, “The happiness of your life depends upon the quality of your thoughts: therefore, guard accordingly, and take care that you entertain no notions unsuitable to virtue and reasonable nature” (Meditations 10:10). These reflections, on food as merely dead flesh, on sex as nothing more than friction and a spurt of mucus, on stripping away vanity to reveal the shabbiness of things and the insignificance of our work, are the kinds of virtuous and rational thoughts upon which, in Stoicism, true happiness depends.
Eeyore, though perhaps unaware of Stoic doctrines, embodies their spirit. Let’s call him a natural Stoic, one inclined by temperament toward the core tenets of Stoicism without needing to study its theory.

In his introductory story something is intruding into Eeyore’s customary thoughtfulness. He typically has a How, but that How has eluded him. The issue, it turns out, is that Eeyore has lost his tail, where his How resides. Without the How, Eeyore is cut off from his philosophical grounding and cannot live his life of harmonious rationality and self-control.
Pooh sees that Eeyore has lost his tail and offers to find it for him. Eeyore thanks him.
“You’re a real friend,” said he. “Not like Some,” he said.
And is that not simply the truth? Eeyore knows that real friends help each other on the path of Stoic virtue, and “some” friends are “not like” that. Real friends help us recover our How, the grounding, the reason, the internal coherence that allows us to live well.
For the Stoic Eeyore, virtue and wisdom are the highest goods, far above pleasure, reputation or material success. A lost tail is a minor tragedy by ordinary standards, but for Eeyore, it is a disruption of reason, and therefore a disruption of virtue. Friends, for the Stoic sage, are fellow travelers on the path of virtue. In offering to help Eeyore, Pooh becomes a companion in the pursuit of the good, performing not just a kind act but a virtuous one.
Pooh does indeed find Eeyore’s tail. Owl, thinking it a door knocker no one wanted, had taken it home for that purpose. After Christopher Robin nails the tail back on, “Eeyore frisked about the forest, waving his tail so happily that Winnie-the-Pooh came over all funny, and had to hurry home for a little snack of something to sustain him.”
Eeyore got his How back.

