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Timeless Wisdom From Winnie the Pooh

Lovable, huggable Winnie the Pooh has long captivated audiences with his jolly laugh and zest for life (and honey). But this sweet bear and his beloved buddies do more than entertain fans with tales from the Hundred Acre Woods. The characters navigate life’s ups and downs, with helpful advice that’s relevant well beyond Christopher Robin’s neighborhood.

It all starts with author A.A. Milne. The mastermind behind the original four-volume Winnie-the-Pooh series is renowned for his children’s stories — his gentle Pooh Bear gave rise to a wildly popular franchise beloved around the world, with the help of Walt Disney’s animated films and television shows. But Milne was also an intellectual writer and deep thinker, which is reflected through the abiding wisdom of Pooh and his pals.

Milne graduated from the University of Cambridge, and wrote his first play, Wurzel-Flummery, while serving in the British Army’s Royal Corps of Signals during World War I. He went on to make a name for himself as a playwright and, later, a novelist. All along, his calling as a children’s author was taking shape — and it’s largely thanks to his own son, Christopher Robin Milne, proud owner of the sweet little stuffed bear audiences worldwide now call Pooh.

From the first Winnie-the-Pooh book in 1926, Milne and illustrator E. H. Shepard took Pooh and his pals through many of life’s twists and turns, much to the despair of eternally gloomy Eeyore. Through it all, Pooh, Piglet, and the Hundred Acre gang showed readers how to cherish life’s best moments and navigate through the worst of them. Almost 100 years later, this Hundred Acre wisdom couldn’t be more relevant.

You can't stay in your corner of the forest waiting for others to come to you. You have to go to them sometimes.
Pooh, "Pooh's Little Instruction Book"

As Pooh “notes” in his little instruction book, life is about more than cozying up in our favorite corners, or staying in our safe spaces to avoid the unknown. Putting ourselves out there leads to new experiences, important lessons, and valuable friendships we’d never form staying safe at home. There’s a dazzling, enriching world just waiting beyond our comfort zones, if we’re brave enough to leave our corner of the forest.

If ever there is tomorrow when we're not together, there is something you must always remember. You are braver than you believe, stronger than you seem, and smarter than you think. But the most important thing is, even if we're apart, I'll always be with you.
Christopher Robin, "Pooh's Grand Adventure: The Search for Christopher Robin"

This sweet conversation between Christopher Robin and Pooh is relatable, and even tear-jerking, for anyone who has experienced loss. The young Christopher Robin wants his best friend Pooh to know that if they were ever to be separated one day, Pooh has everything he needs to carry on and fulfill his dreams. It’s a lesson for us all. While our loved ones may be gone, their spirit and memories live on, and the strong bonds we’ve built make us braver, stronger, and smarter than we realize — just like Winnie the Pooh.

You find sometimes that a Thing which seemed very Thingish inside you is quite different when it gets out into the open and has other people looking at it.
Pooh, "The House at Pooh Corner"

He may be a silly old bear, but Pooh was onto something with his knack for collaboration. In chapter six of The House at Pooh Corner, Pooh came up with a new game. But like most ideas, the game didn’t blossom until he shared it with others. In this case, it took Eeyore joining in for Pooh’s little game to take shape. This lesson extends well beyond lighthearted fun; the more we share our ideas and collaborate on our work and dreams, the better we can see and understand them ourselves.  

The things that make me different are the things that make me me.
Piglet’s song, You’re the One and Only One, "Welcome to Pooh Corner"

As Piglet and Eeyore sing a duet about individuality, this line strikes a chord. Differences set us apart from each other; they fill our world with vibrancy, variety, and beauty. We need all people, from all walks of life, to use their unique skills and personality traits to make this world a better, creative, and inspiring place. Because, as Piglet concludes, “If everybody were like everybody else, how boring would it be!”

They’re funny things, Accidents. You never have them till you’re having them.
Eeyore, "The House at Pooh Corner"

Cautious and nervous Eeyore worried a lot about life, but deep down this donkey knew that anxiety would only get him so far. Life’s mishaps don’t wait for us to feel prepared. Ready or not, accidents hit us full force — and to be fair, that’s not all bad. Acknowledging that accidents will always happen means we can stop overanalyzing the risks. We should resist the temptation to keep endlessly planning and preparing but never getting started,  because at some point, procrastination is simply fear of failure in disguise.

Don't underestimate the value of doing nothing, of just going along, listening to all the things you can't hear, and not bothering.
Pooh, "Pooh's Little Instruction Book"

If only Pooh knew how relevant this advice would become — especially to the parents of Winnie the Pooh’s youngest fans. Western society praises the go-go-go work ethic, but “always on” does not lead to a life of happiness. When we take time to unplug, close our emails, and simply look at the world around us, we can connect with ourselves on a deeper level. In fact, while staring into the ocean may feel like doing nothing, this kind of “nothing” is one of the most enriching and gratitude-building experiences on the planet.

A little Consideration, a little Thought for Others, makes all the difference.
Eeyore, "Winnie-the-Pooh"

It’s no secret that Eeyore is prone to sadness; this makes him the perfect case study on why we should treat everyone with kindness. We never know a person’s backstory, or the troubles they’re currently navigating. It’s best to treat each person with a dose of compassion, thinking about how we can help them instead of how much we have going on in our own lives. Even the tiniest bit of consideration and thoughtfulness could make a world of difference for someone else — whether it’s gloomy Eeyore who needs a pick-me-up, or the taxi driver who’s burnt out trying to make ends meet for their family.

We can’t all, and some of us don’t. That’s all there is to it.
Eeyore, "Winnie-the-Pooh"

On the surface, this may sound like another one of Eeyore’s pessimistic musings, but Pooh’s buddy is right. The sooner we know and accept our limits, the sooner we can find happiness and contentedness — and it all starts with removing “should” from our vocabulary. “Should” is one of the most dangerous words in the English language. If we dislike doing something but feel guilty because society tells us we “should,” we’ll forever feel less-than or inauthentic. Eeyore’s simple statement reminds us to ditch the guilt, dig deep, and understand what you can do, especially the things you enjoy. .

And he respects Owl, because you can't help respecting anyone who can spell Tuesday, even if he doesn't spell it right; but spelling isn't everything. There are days when spelling Tuesday simply doesn't count.
Rabbit, "The House at Pooh Corner"

Rabbit was perhaps the most intelligent of Pooh’s pals, but that wasn’t always a good thing. Sometimes Rabbit judged his neighbors for their silly ideas, or put them down because he knew better. Over time, though, Rabbit realized that smarts aren’t everything. He saw how Christopher Robin respected Owl deeply, despite his mistakes. And this lesson — to respect everyone, mistakes and all — is more than advice for Rabbit; it’s a reminder for us all.

Photo credit: Claudio Testa/ Unsplash

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About the Author
Stephanie Vermillion
Stephanie is an Ohio-based writer and photographer who's never met a slice of pizza she didn't like — or inhale.
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