'Winnie the Pooh' by A.A. Milne

5 Life Lessons from Winnie the Pooh

As the autumn leaves dance around your feet and the old oak trees bow over tangled forest pathways, take a trip down memory lane as we commemorate the best quotes and life lessons from Winnie the Pooh.  

There is a deep connection between the inner child and that clumsy yellow bear. As children we didn’t notice, but Christopher Robin, Pooh, Tigger, Rabbit, Eeyore, Kanga, Roo, Piglet, and Owl were responsible for many life lessons that have guided us through our teen and adult years. We’ll blow the cobwebs off a few timeless Winnie the Pooh friendship quotes and show you some stunning pieces from Short Story’s collectors’ range along the way. 

Put on your wellingtons - it’s time to explore the Hundred Acre Woods.

Winnie the Pooh Books

A.A Milne based the Winnie the Pooh books on his son Christopher Robin Milne. After a brief yet inspiring encounter at the London Zoo with a very real bear named Winnie and a swan named Pooh, Christopher decided to call his beloved teddy bear Winnie the Pooh. 

A.A Milne processed the hardships and obstacles children face in friendships, including the physical and emotional challenges, love, and hard goodbyes, into a fantasy format constructed around the plush toys that belonged to his son.

The first publication of the adorable honey-loving bear appeared in 1926. In 1960 Walt Disney attained the licensing to develop Winnie the Pooh’s television identity, starting with the featurette film ‘Winnie the Pooh and the Honey Tree’ that was released six years later. Walt Disney Studios has since created an empire from the franchise, and today it records $5.5 billion of the $25 billion total that Disney generates each year. One of the many reasons that it has lasted almost 100 years since its primary conception is the genuine nature of the show, with parents continuing to support the franchise because of its moral teachings and the impression it makes on children. 

So let’s take a look at the 5 life lessons from Winnie the Pooh and the Hundred Acre Woods gang that have influenced our lives to this day.

Lesson No. 1 - Acceptance and Friendship

Each character in this beautiful world created by A.A Milne is said to represent aspects of mental health that most individuals will experience in their teen and adult lives. Conveying this normality in the animations helps children understand what it’s like to feel sad, anxious, hyperactive, or obsessive over something, even if it is just honey.

But in the Disney short ‘Day for a Donkey’, Piglet is exposed to the fact that people deal with their emotions differently. 

While Eeyore sits glumly, grazing on the hill, Piglet notices how sad he looks and decides to try and cheer him up. With how supportive and involved the whole Acre Woods community is, they decide to take Eeyore on their favourite activities in the pursuit of happiness.

As honey eating, flying, jumping, and gardening all seem to end in a terrible crash, bang, and boom, Piglet struggles to think of what makes him happy and what activity he will share with Eeyore. As he clambers up the hill to apologise, Eeyore insists that he is happy and that he comes to this hill for his favourite activity of all - cloud gazing. 

What to Take Away

Everyone is unique in the way they process their emotions and develop activities that make them feel happy. Friendship is about accepting these differences along with each other’s similarities.

One of the best Winnie the Pooh friendship quotes from A.A Milnes’ ‘Piglet’ states;

“The things that make me different are the things that make me, ME.”

Accepting your friends for who they are and what they like is the key to a strong friendship. One of our favourite Winnie the Pooh friendship quotes here at Short Story captures the innocence and beauty of how a pure friendship can make you feel.

“How lucky am I to have something that makes saying goodbye so hard” - Winnie the Pooh.


Lesson No. 2 - The importance of love and being present in the moment

With Winnie the Pooh, love is at the heart of everything. But Rabbit, a character so caught up in order and the maintenance of his garden, tends to only choose friendship over order as a result of guilt. This remains true until the episode titled ‘Find Her, Keep Her’, where Rabbit discovers the true meaning of unconditional love and remaining present in the moment.

A harsh storm sweeps over the Hundred Acre Woods, leaving a baby bird named Kessie stranded in the cold. Rabbit takes her under his wing - so to speak - and develops a father-daughter-like relationship. As winter turns to spring, Kessie starts to discover her origins and takes flying lessons with Mr Owl in preparation to fly South the following winter. 

Rabbit, who is afraid of heights, forbids Kessie from flying in case something terrible happens. As a result, Kessie is forced to rebel against Rabbit and prepares to migrate. Flooded with guilt, Rabbit decides that he must give his blessing to Kessie before she takes off without saying goodbye. As they embrace for the last time in a long time, Piglet tells Pooh that for the longest time he thought that Rabbit didn’t like Kessie, to which one of the best Winnie the Pooh quotes arises:

“Sometimes, people care too much. I believe it’s called… love.” - Winnie the Pooh.

What to Take Away

Love outweighs any reason or logic. This is a lesson for children and parents, because Rabbit learns that he must trust Kessie and let her live up to what she was destined to do… fly! That doesn’t mean you should let your children attempt the art of flying, per se, but instead to test themselves and evolve their independence to eventually shape the amazing and unique individuals they are destined to be!

Throughout life, we are faced with hard goodbyes and things that must come to an end. This specific tale teaches us to stay present and live in the moment. Rabbit was so focused on the inevitable fact that Kessie would leave one day that he forgot to enjoy the time that he did have looking after her and creating memories. This springs to mind a gorgeous Winnie the Pooh quote:

”What day is it?”  “It’s today.” “My favourite day.”  - Pooh and Piglet.

So love immensely and live presently. 

Lesson No. 3 - Enjoying food with gratitude

We all know that Winnie the Pooh loves food, particularly that golden nectar we call honey. Now, this life lesson coincides with the last - living in the moment and appreciating the small things, like a home-cooked meal, going out for dinner at your favourite restaurant, or finding the best snack to watch with your favourite Disney movie. If you love food as much as we do, you can agree that it feeds the belly as much as it feeds the soul. 

“What could be more important than a little something to eat?” - Winnie the Pooh.

What to Take Away

Even when we are going through a bit of a rough patch, it’s important to be grateful for both the small things, like food, exercise, and the nature that surrounds us, along with the bigger things like friendships and families. Gratitude shows appreciation, which contributes to the longevity of that very thing that’s bringing you happiness. 

Winnie the Pooh eating honey.


Lesson No. 4 - Keep smiling and be kind to others

It’s hard to know what people are feeling. As we grow older, we learn to put on masks of confidence, assuring the people around us that we are okay. Have you ever had a particularly bad day for no reason at all, and with one smile or act of kindness, someone turned your mood around? That is the life lesson that Winnie the Pooh and the gang are constantly trying to tell us. 

“Always wear a smile, cause your smile is the reason for others to smile.” - Winnie the Pooh

A common theme in the Winnie the Pooh series involves someone getting into a spot of trouble, with the resolution brought along by the remainder of the forest creatures showing consideration to the friend in need. In one particular episode, Eeyore states:

“A little consideration, a little thought for others, makes all the difference.” - Eeyore.

What to Take Away

Remember that anyone could be going through a tough time, and greeting someone with a smile and a little consideration could change the trajectory of their day and even their life. It’s funny how a small gesture can have a massive impact!

Lesson No. 5 - Be Brave

During ‘Winnie the Pooh’s Grand Adventure’, the Hundred Acre Woods crew are faced with a hairy predicament where they must find young Christopher Robin who’s lost in the woods...or so they think.

Christopher Robin says to Pooh at the start of the movie:

“You are braver than you believe, stronger than you seem, and smarter than you think.”  - Christopher Robin.

Along their journey to find the young lad, they discover the true meaning behind what their dear friend meant.

What To Take Away

It’s easy to forget that as kids, everything is bigger, scarier and unknown. One of the many life lessons from Winnie the Pooh teaches us that it’s okay to be scared, but we must respond with bravery. The unknown is only scary if it remains unknown.

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