12 Winnie-the-Pooh Philosophies To Help Make Sense Of Life

Kirstie Taylor
Jun 18 · 6 min read

I have fond memories of a bare-bottom yellow bear venturing around the forest with his eclectic group of animal friends. His obsession with honey was endearing, and every time he exclaimed “Oh, bother!” it felt all too familiar; a dear friend just up to his own antics again.

But as a child, I experienced Winnie the Pooh from a surface level. I consumed the TV show version of the tales that went off the air a mere six months before I was born. I collected the gold and black spined-books of the Little Golden Book series that chronicled the Hundred Acre Wood adventures.

I never knew of the more profound meaning that lurked behind the words my mother read aloud to me. I was completely unaware of the ideas A.A. Milne tried to convey to his son, the real Christopher Robin, through innocent ventures of misfit animals.

But now that I’ve grown up, and I’ve come across Winnie-the-Pooh’s wisdom applied to the way people make sense of the world today, I am enchanted once again. The words are no longer a fairytale to me, they’re something much deeper.

Being in my 20's — a time I have come to accept as my formative years — the words of the Hundred Acre Wood clan are much needed and ring true to me more than ever before.


So here is my interpretation and application, as a young adult still figuring out life, of the philosophies of Winnie-the-Pooh:

“You can’t stay in your corner of the Forest waiting for others to come to you. You have to go to them sometimes.”

You can’t wait for things to happen to you. Sometimes, you have to go out and make them happen for yourself. When you play it safe and stay in your comfort zone, you won’t achieve your dreams. Sometimes it seems easier to sit back and wait for things to come to you; blame others for how life plays out; makes excuses as to why you need to keep in your safety bubble.

But the most rewarding parts of life lie in the fray. They’re in the unknown and require bravery and effort. Sure, it’s scary. But the best does not come easily.


“Some people care too much. I think it’s called love.”

What a beautiful way to think about love. Or is it pessimistic? Coming from Pooh Bear, I’d say it’s a mixture. Caring for someone genuinely is the essence of Pooh’s being, but at the same time, I think he realizes when someone’s care can be taken for granted.

Some people are willing to give there all to those they care about. Then there are those that receive that care and don’t appreciate it. This phenomena between people isn’t black and white. But somewhere in there, there’s love.


“Rivers know this: there is no hurry. We shall get there someday.”

Rushing to get through milestones in life is going against the flow of life. There’s no need to hurry to accomplish something, find a partner, or have kids by a certain age. As long as you’re making progress, doing what brings you joy, and living in alignment with what your heart wants, things will come into your life when they’re meant to.


“If the person you are talking to doesn’t appear to be listening, be patient. It may simply be that he has a small piece of fluff in his ear.”

I love this quote. I actually first heard it in Tony Hsieh’s book, Delivering Happiness.

Not everyone is going to understand you right away; not everyone will see things from your perspective from the get-go. Give people time. You don’t know what’s going on in their life. Patience is key when it comes to human interaction.


“I don’t feel very much like Pooh today,” said Pooh.
“There there,” said Piglet. “I’ll bring you tea and honey until you do.”

Sometimes, you’re going to have some off days. Take care of yourself; have some tea and honey. Don’t create unnecessary pressure for merely being human. You’re allowed days when you just need to rest and pick things up again tomorrow.


“Well,” said Pooh, “what I like best,” and then he had to stop and think. Because although Eating Honey was a very good thing to do, there was a moment just before you began to eat it which was better than when you were, but he didn’t know what it was called.”

Have you ever considered how good it feels to plan a trip? The days before you get on the plane, you’re so excited for everything to come and perhaps that feeling is as good, if not better, than actually being on the trip.

Excitement mixed with anticipation is a strong emotion. We often don’t stop and indulge in this feeling. Next time you find yourself in this state, allow yourself to really enjoy it.


“Just because an animal is large, it doesn’t mean he doesn’t want kindness; however big Tigger seems to be, remember that he wants as much kindness as Roo.”

Simply, don’t judge a book by its cover. Tigger may be big and would lead to assumptions that he’s scary and aggressive. But deep down, he’s just wanting to be loved like everyone else.

People are innately the same. Just because someone looks different than you, doesn’t mean they don’t have the same desires and emotions. And you’ll never be able to tell that about someone by merely looking at them.


“You’re braver than you believe and stronger and smarter than you think.”

We underestimate ourselves all the time. We question our abilities, but it’s human nature not fully to realize how much we’re capable of. Next time you find yourself doubting what you can accomplish, remember this quote.


“Rabbit’s clever,” said Pooh thoughtfully.
“Yes,” said Piglet, “Rabbit’s clever.”
“And he has Brain.”
“Yes,” said Piglet, “Rabbit has Brain.”
There was a long silence.
“I suppose,” said Pooh, “that that’s why he never understands anything.”

Intelligence sometimes inhibits a person from understanding a simple situation. Not everything needs to be overthought. Not everything needs to be deeply evaluated.

Sometimes the answer is simple and straight forward.


“It is more fun to talk with someone who doesn’t use long, difficult words but rather short, easy words, like ‘What about lunch?’”

Writers may relate to this on a deeper level than most. But what I think this quote comes down to is that people don’t need to complicate simple interactions. There’s really no need to impress; no need to make a big deal.

Sometimes, it’s the smallest of interactions that mean the most.


“Don’t underestimate the value of doing nothing, of just going along, listening to all the thing you can’t hear, and not bothering.”

It’s ok to do nothing. It’s perfectly fine to take a break.

In fact, in a culture where we’re used to be told to always “hustle” and go, go, go, we see doing nothing as a detriment to our character. That we’re in fact lazy or not ambitious if we take a break.

But breaks are good for our sanity. Sometimes we just need to stop: let our body and mind take a little pause. We don’t need to be constantly going.


“I’m not lost for I know where I am. But however, where I am may be lost.”

Uncertainty in life is inevitable. We can never be sure of the path we’re going down. But not knowing what is exactly going on doesn’t mean you’re wrong. And you can feel secure in the uncertainty.


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Kirstie Taylor

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Writer and podcast host for relationships and psychology. Newsletter: https://kirstietaylor.substack.com

The Startup

Medium's largest active publication, followed by +477K people. Follow to join our community.