Harmonious Tales from the Hundred Acre Wood — Life Lesson’s Through Pooh’s Wisdom

The Podcasting Store
3 min readOct 5, 2023

By Drew Holmes

Timothy and Sam enjoying tales from the Hundred Acre Wood

“Read to me, dad!” came the urgent request.

Sam, my five-year-old, was ready for his bedtime story and, just like each night for the last few weeks, wanted a story from Winnie the Pooh.

“Of course, buddy! I’d be glad to.”

I had last read A. A. Milne’s work when I was his age and the renewed acquaintance with familiar friends was long overdue.

As we shared stories of Pooh tracking a Woozle, Eeyore losing his tail, or Piglet’s house getting flooded in a rainstorm, my perspective on the Hundred Acre Wood was slowly changing. These were children’s stories, no doubt, but the lessons ran much deeper than I had realized.

Most obvious is Eeyore who, to modern eyes, is clinically depressed. Nothing good is ever expected in his world nor does he typically revel in joy. Losing his tail or falling into the river is just the way things are in his mind. Despite the negativity, Eeyore sets two positive examples. First, he is mentally tough and resilient. Nothing gets him so down that he withdraws from the world or opts out of new experiences. And second, no one avoids, taunts, or tries to change him. Eeyore is unconditionally loved and accepted just the way he is.

Diminutive Piglet teaches us something different but equally important. He is always self-conscious of his small statue, unsure of how to contribute. But time and time again the Friends include him, even using his size to everyone’s benefit when Owl’s house collapses and he, Owl, and Pooh need to escape. Piglet demonstrates that even the smallest person can have a big heart.

Owl is an interesting character as well. Though he is one of the more educated Friends, he frequently makes up facts and misspells words. Once again, everyone accepts him and his eccentricities without question, frequently looking to him for his vast knowledge. Owl is clearly a reminder that the wise don’t know everything, but you don’t need to know everything to be wise.

And who can forget the exuberance of Tigger? His over-the-top enthusiasm and limitless supply of positive energy is a direct foil to Eeyore and, just like Eeyore, he is accepted unconditionally by the Friends. Though his constant bouncing and extreme extroversion can be frustrating at times (especially to Rabbit), he is loved and included just the same.

Pooh is characterized time and time again as a Bear of Very Little Brain. However, at every turn he proves that to be an oversimplification. Whether building a boat during the flood or making a house for Eeyore, he proves that you do not need to be a genius to have good ideas. And all of Pooh’s best ideas come when he is trying to do something to help someone else. Once again, the size of your brain is eclipsed by the size of your heart.

These lessons are not specific to the Hundred Acre Wood, but also have profound relevance to music making. When in an ensemble, everyone has something to contribute. An individual musician may not be the flashiest, smartest, or outgoing, but they add something vital to the group. Music creates family. Supporting each person’s unique strengths and accepting them for who they are is the foundation of that family. After that, the notes take care of themselves.

We finish reading the story of Pooh, disguised as a rain cloud, and the Bees trying to protect their honey. I can’t help but marvel at the joyous smile on Sam’s face as he drifts off to sleep. Someday he will understand the real lessons behind these tales and know he was learning how to be a good friend. But for now, he can just love that silly old Bear.



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