About two years ago now, I shared a Sermon on lessons from the stories of Winnie the Pooh and his Friends. I remember that my reflections sparked a lot of conversation as people recalled with fondness their own memories of reading those precious stories. Winnie the Pooh seemed to evoke some wonderful and comforting memories from childhood for those who were with us that day. I don’t know about you, but I sense that we could use a big helping of comfort these days as life just keeps coming at us and as our hearts become overwhelmed by the sorrows of the world, so I thought it might be helpful to return to Winnie the Pooh and discover other lessons from these precious stories. “Sometimes,” said Pooh, “the smallest things take up the most room in your heart.” And so this morning, let us open our hearts once again in prayer, Let us pray, O God of hope and wonder, we thank you for the comfort you share with us; we thank you for the moments shared, the stories told, and the times of joy and quiet. Help us to continue to nurture such moments even today in the midst of the things that may weigh upon our hearts. Grant us times of solace and of peace. Amen.
Many of us may hold a special place in our hearts for memories of special childhood books and of the stories of Winnie the Pooh and his friends. These stories by A.A. Milne, were first published in October of 1926, nearly a century ago. Milne wrote the stories of Winnie-the-Pooh and its sequel, The House at Pooh Corner (1928), for his young son, Christopher Robin, whose toy animals were the inspiration for many of the characters and whose name was used for the young boy who appears in the stories as the loving companion of the animals. We all remember that Pooh Bear was a teddy bear with very human characteristics, an ordinary bear as he was sometimes called who was able to capture the imagination of children. The author used a bear, a tiger, a donkey and a piglet to teach children about some of the lessons in life—including friendship with all of it ups and downs.
As most of you may recall, the main character, Winnie-the-Pooh (sometimes called simply Pooh or Edward Bear), is a good-natured, yellow-furred, honey-loving bear who lives in the Forest surrounding the Hundred Acre Wood, modeled after Ashdown Forest in East Sussex, England. His friends included Eeyore, a gloomy gray donkey; Piglet, a timid pig; Owl, a rather opinionated bird; the meddlesome Rabbit; and Kanga, an energetic kangaroo whose inquisitive baby, Roo, lives in her pouch. Pooh, was described as a “Bear of Very Little Brain,” who finds himself in all kinds of sticky situations and the stories speak of his many silly adventures. As the author wrote, “Christopher Robin was sitting outside his door, putting on his Big Boots. As soon as he saw the Big Boots, Pooh knew that an Adventure was going to happen, and he brushed the honey off his nose with the back of his paw, and spruced himself up as well as he could, so as to look Ready for Anything.”
The stories are simply written, to appeal to young readers and notable for the rich insights into human behaviour. The characters are endearing but also complex and the sweet illustrations by E.H. Shepard helped make the books a children’s classic. In The House at Pooh Corner, another popular character arrives- the exuberant tiger named Tigger, known for his quote, “the wonderful thing about tiggers is I’m the only one!”
In his piece, The Hundred Acre Lessons: What Winnie the Pooh and Friends Still Teach Me Today, writer Andrew J. Mair
Shares his thoughts on some of the lessons we may draw from these ageless stories.
Mair writes, “Deep in the Hundred Acre Wood, where the trees whispered and friends wandered…
“Growing up with A.A. Milne’s Winnie the Pooh, I thought I was just reading sweet stories about a bear who loved honey and his quirky friends in the Hundred Acre Wood. But as an adult, I’ve come to realize that each character carries a deeper truth — lessons that resonated with me as a child and continue to offer guidance in adulthood. The simplicity of these stories hides profound wisdom, shaping not just how we see the world as children, but how we navigate its complexities as adults. Though the stories were simple, each character in the Hundred Acre Wood carried a depth that went beyond childhood adventures. They weren’t just a bear, a piglet, or a gloomy donkey — they were reflections of the emotions, challenges, and joys we all experience, no matter our age.”
This morning, as we seek out moments of contentment and peace, what lessons may we still learn from these stories that may inspire us in such times as these?
Winnie the Pooh — Contentment and Presence
Pooh teaches the simple joy of living in the moment. Whether he’s enjoying a pot of honey or sitting quietly with friends, Pooh shows kids that happiness isn’t about having everything, but cherishing what’s right in front of you. Pooh reminds me to slow down, appreciate the small moments, and find contentment in just being. His famous line, “Doing nothing often leads to the very best of something,” is a lesson in mindfulness, teaching us to embrace life’s pauses without guilt.
Piglet may teach us about Courage and Vulnerability
Despite being the smallest and most timid, Piglet faces his fears time and again. He teaches children that courage isn’t about being fearless; it’s about moving forward even when you’re scared. He says at one point, “The things that make me different are the things that make me ME.” Life often requires us to step into uncertainty — whether in relationships, careers, or personal growth. Piglet shows us that it’s okay to feel small or overwhelmed, and that leaning on friends (or community) isn’t a weakness but a strength. Piglet asks Pooh at one time, “How do you spell love?” Pooh: “You don’t spell it. You feel it.”
Eeyore shares important insights on Acceptance and Compassion
Eeyore’s gloomy outlook is met with patience and kindness by his friends. I recall a childhood show based on the adventures of Pooh. Many of Eeyore’s friends saw him sitting on a hilltop all alone and staring out in the distance. They were very concerned that he was alone and perhaps quite sad and so they decided they should go and keep him company. When they arrived and asked Eeyore why he was feeling so down, he told them that he wasn’t feeling sad, he was gazing out at the rainbow out in the distance in the sky and they all sat down and joined him in this precious moment. Eeyore helps his friends, as well as young readers learn the importance of accepting others as they are, even if they’re different or difficult to understand. Throughout our lives, we meet people (and even parts of ourselves) that carry a bit of Eeyore’s melancholy. His character reminds us to offer compassion to those who struggle, without trying to “fix” them. Sometimes, just showing up and listening to someone’s feelings is enough. It’s okay to not always be cheerful. The people who truly love us will accept us even when we are going through difficult or sad times.
Tigger is a character with incredible Enthusiasm. He possesses tremendous energy and self-confidence, and may teach kids to embrace life with enthusiasm and to be unapologetically themselves.
While Tigger’s exuberance is infectious, it’s also important to balance that enthusiasm with respect for others’ boundaries. Tigger reminds us that it’s great to be confident and lively, but it’s also important to recognize when our energy might overwhelm those around us. Finding the balance between joy and sensitivity is a lifelong lesson. Pooh observes wisely, “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.”
Rabbit — Responsibility and Flexibility
Rabbit is the planner, always trying to organize things and keep everyone in line. He teaches children about responsibility and structure. Rabbit also represents the challenge of wanting to find control in an unpredictable world. While planning is often important, Rabbit also reminds us that life often doesn’t work out as we plan. Sometimes, we need to let go of that search for perfection and embrace the unexpected — because often, that’s where the magic happens.
“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.”
Owl shares important lessons on Wisdom and Humility
Owl is considered the “wise one” in this special group of friends, often sharing advice (whether it’s needed or not). Readers may learn that wisdom isn’t just about knowledge but also about understanding and listening. For us as adults, Owl shows the fine line between confidence and arrogance. True wisdom often comes with humility — the ability to admit when we’re wrong or don’t have all the answers. Owl reminds us to stay curious and open-minded.
And wonderful, sweet Christopher Robin teaches us about growing up and Letting Go. Christopher Robin is the one that holds the group together, embodying the innocence and wonder of childhood. His adventures with Pooh and his friends have much to teach children and us about imagination and friendship. Perhaps the most bittersweet realization comes with Christopher Robin’s gradual departure from the Hundred Acre Wood. Growing up means change — saying goodbye to certain phases of life while carrying their lessons forward. His story reminds us that it’s okay to let go of childhood, but it’s just as important to hold onto its wonder and simplicity, no matter how old we get. In the story, When We Were Young, we hear Christopher Robin saying his prayers… “Oh! Thank you, God, for a lovely day. And what was the other I had to say? (he tries to remember) I said “Bless Daddy,” so what can it be? Oh! Now I remember. God bless Me.”
The Winnie the Pooh stories aren’t just nostalgic tales from my childhood — they’re timeless lessons that have grown with me. Each character represents a different part of who we are at different stages of life, reminding us that no matter how complex adulthood becomes, the simple truths from the Hundred Acre Wood still guide us. As Pooh wisely said, “You’re braver than you believe, stronger than you seem, and smarter than you think.” And sometimes, that’s all we need to remember. We may all wish that life were only as simple as the 100 Acre Woods.
(https://medium.com/andrew-j-mair-author/the-hundred-acre-lessons-d61109051f7e)
“A little consideration, a little thought for others, makes all the difference.”
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“Piglet noticed that even though he had a very small heart, it could hold a rather large amount of gratitude.”
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“Weeds are flowers too, once you get to know them.”
Love Brings Happiness to Ourselves and Others
Piglet: “How do you spell love?” Pooh: “You don’t spell it. You feel it.”
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“Love is taking a few steps backwards, maybe even more, to give way to the happiness of the person you love.”