“You Shall Love Your Neighbor As Yourself” (Leviticus 19:18)

Winnie the Pooh says, “How Lucky I Am To Have Something That Makes Saying Goodbye So Hard.”

Winnie The Pooh


Most people don’t realize how much effort it takes to write something that is simple yet meaningful. Yet, the author of Winnie the Pooh, A.A. Miline, was able to communicate the meaning of a message that readers of any age could understand. That is one of love, friendship, responsibility, and profound loss.

A.A. Miline told us through Winnie the Pooh that love is precious and friends are forever. She also told us that life is fragile and the richer and deeper our relationships the more painful it is to say goodbye.

But is Winnie the Pooh correct? Was the Pooh Bear lucky to have experienced a depth of love so great that saying goodbye was hard? And what about when one has to say goodbye to a child, a spouse, or a parent? Are we lucky when the pain of saying goodbye is so great that it seems unbearable?

A.A. Miline decided to also write about Eeyore, the donkey. Eeyore had a very different view of life, friendship, and fellowship.

Eeyore is always depressed and avoids emotion. He doesn’t have deep connections with the other characters in The Hundred Acre Wood.

Instead of going out of his way for others, Eeyore makes little effort to be anyone’s friend. He is unhappy. He disconnects from the society around him. He does not even think he is worthy of friendship or happiness. Eeyore is neither selfless nor kind. He essentially lives by himself and goes weeks at a time without contact with the other animals.

But Eeyore has some attributes that we value in today’s society. He is independent and smart and can take care of himself without help from others. Eeyore isn’t a very needy character and like real-life donkeys, Eeyore can make it in the wild for extended periods of time on his own.

Picture of EEyore from Winnie the Pooh.

But, Winnie the Pooh is a flawed personality; he isn’t smart, sophisticated, or worldly. He is always hungry, has an insatiable appetite, little self-control, and a desire to eat honey (a flaw I have in human form). Winnie the Pooh is always getting into trouble that only his friends can get him out of, and it seems he can’t survive even for a day on his own. In short, Winnie the Pooh is a needy character which is generally not a trait that is prized.

But Winnie the Pooh is happy. He is comfortable in his own skin and is sociable, kind, and loyal. Winnie the Pooh knows how to live life to its fullest and is a role model for the animals in the Hundred Acre Wood. And, in case anyone didn’t understand the importance of Winnie the Pooh, he is the best friend of Christopher Robin and all of the animals in Hundred Acre Wood.

A.A. Milne presents a clear choice; do we want to live and love like Winnie the Pooh despite the Pooh Bear’s obvious flaws and shortcomings? Or is it better to get along and be alone like Eeyore, but without being invested in the society around us?

Do You Live Life Like Winnie The Pooh?

I choose to live my life like the Pooh Bear.

Laughing Winnie The Pooh.

A Life Well Lived can only be a life that is full of love, fun, food, and relationships. I know that one of the downsides of the life I have chosen is it is unpredictable and sometimes chaotic. And, I know that sooner or later I will suffer the pain of saying goodbye to people I love. But until then, my life is rich and full.

Like Winnie the Pooh I am lucky because I have many relationships that will make saying goodbye so very hard; almost unbearable.

I knew as I wrote this that some people will criticize me for being trite and cutesy by gleaning meaning from a children’s book. But what is trite about the most fundamental lessons that we teach our children? What is cutesy about A.A. Milne words penned almost 100 years ago, even if they were written for children?

Winnie the Pooh is foundational, classic, and non-pretentious. For those that want a more sophisticated version of Winnie the Pooh, we only need to read the words of The Right Honorable Lord Alfred Tennyson’s immortal poem In Memoriam A.H.H. In this poem, Lord Tennyson wrote about the loss of his closest friend and the pain of his loss.

I hold it true, whate’er befall;

I feel it when I sorrow most;

‘Tis better to have loved and lost

Than never to have loved at all.

Mark Sunshine

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