The misunderstood Bravery of Eeyore

I won't say no, I won't say can't, I won't say I won't try

.

Eeyore's bravery in Winnie the Pooh is not demonstrated through grand heroic acts but through his quiet resilience and acceptance of himself. Although he's often seen as melancholy with a negative outlook, he consistently takes part in his friends' adventures, showcasing a bravery of spirit in facing the world despite his pessimism.

I read an article years ago that shed a entirely new light on the character of Eeyore from Winnie the Pooh. It was by someone I don't know named Donna Dickens, and I thought it was very insightful. I will try my best to accentuate the ideas and add the her post below

Here’s a more detailed look at Eeyore’s subtle bravery:

Participating Despite Negativity:
Eeyore frequently expresses doubt and fear, yet he rarely refuses to join his friends. He attends Pooh’s parties, explores the forest, and even helps in tasks like finding Owl a new house.

Accepting His Flaws:
He embraces his melancholy and pessimistic tendencies, making him a relatable character. Rather than trying to force positivity, Eeyore accepts and shares his unique perspective.

Loyalty to Friends:
Despite his own struggles, Eeyore remains loyal and supportive. He offers helpful advice—even if delivered with negativity—and is always willing to lend a helping hand.

Being True to Himself:
Eeyore’s bravery lies in his willingness to be himself, even when others might not fully understand or appreciate his outlook. His comfort in his own skin, flaws and all, exemplifies a form of bravery in itself.

For nearly a century, children have adored A.A. Milne’s characters from Winnie-the-Pooh. These timeless stuffed toys, brought to life through stories and adaptations, resonate with both children and adults. Pooh embodies innocence, Piglet symbolizes anxiety, Tigger represents boisterousness, and Eeyore? Eeyore embodies bravery.

As a child, I watched countless Disney adaptations of Winnie-the-Pooh—times I spent playing Poohsticks, getting muddy, and daring physics-defying stunts. Yet, one thing puzzled me: why couldn’t the gang make Eeyore happy?

I often saw Eeyore feeling dejected and wished I could cheer him up. I’d quietly think, “Someone hug him,” while eating my Rainbow Brite cereal. It seemed like every moment, Eeyore was sad—whether playing Poohsticks, living in his stick house, or mourning his lost tail. I wondered, why wouldn’t someone just sew it back on so he wouldn’t be sad?

Growing older, my empathy was clouded by teenage cynicism. I began to believe that every character in the Hundred-Acre Wood needed psychological help. I couldn’t see the real Eeyore clearly—until I became a parent myself.

Revisiting Winnie-the-Pooh as an adult revealed new layers—especially regarding Eeyore. With my children asking to watch the series repeatedly, I realized Eeyore was teaching two vital lessons simply by existing. He showed children how to include those who aren’t as cheerful and how it’s okay to feel gloomy as long as it doesn’t take over your life. Growing up in a household where negative emotions were stigmatized and depression was unseen, I was conditioned to try “fixing” others’ sadness. Eeyore reminded me that sometimes, acceptance is enough.

In the episode “Winnie-the-Pooh and a Day for Eeyore,” the gang discovers Eeyore is especially sad because no one remembered his birthday. Pooh and Piglet rush to get him gifts; Pooh attempts to give Eeyore honey, but ends up eating it himself, suggesting the idea of a labeled jar for future use. Piglet tries to give him a balloon, which pops, but Eeyore loves the color red and finds joy in the scrap of it he keeps. Ultimately, Christopher Robin hosts a party for Eeyore, and Pooh teaches him how to play Poohsticks—Eeyore’s a natural at it.

What’s truly brave here? Eeyore simply shows up. He accepts his friends’ efforts and kindness. For anyone living with depression, that alone is a monumental feat. Despite his gloomy outlook, Eeyore doesn’t shut himself off. He demonstrates that happiness is an emotion—one that fluctuates—and that being a friend, hanging out, and helping others aren’t necessarily linked to constant cheerfulness.

Throughout his time in the Hundred-Acre Wood, Eeyore consistently shows up for his friends. When Owl loses his house in “Winnie-the-Pooh and the Blustery Day,” Eeyore braves a flood to find him a new home, understanding what it feels like to lose one’s dwelling. When Tigger feels lonely, Eeyore writes “Keep smiling” in a card to lift his spirits. Perhaps most emblematic is his song from the live-action “Welcome to Pooh Corner,” “Never Give Up.” While trying when happy comes easily, trying when feeling gloomy requires real bravery

Bill Bathurst

Donna Dickens