We Could All Be a Little More Like Winnie-the-Pooh

Lindsey Hiltner
The Startup
Published in
5 min readMay 29, 2019
Photo by Annie Spratt on Unsplash

“When you wake up in the morning, Pooh,” said Piglet at last, “what’s the first thing you say to yourself?”

“What’s for breakfast?” said Pooh. “What do you say, Piglet?”

“I say, I wonder what’s going to happen exciting today?” said Piglet.

Pooh nodded thoughtfully.

“It’s the same thing,” he said.

As a kid, one of the biggest questions of my day was what would be served for school lunch. I remember my excitement for chicken nuggets, my disappointment for meatloaf. Now, lunch barely gets a second thought during the day. I throw together a sandwich or grab a bagel to eat while staring at my computer screen.

We make excuses all the time about why a child-like view of the world is infeasible, due to responsibilities or expectations of others. As a consequence, we find ourselves stressed out, trying to fit circular pegs into square holes to have the sort of life we think we need.

I’m no exception. I’ve made the most practical choice at each step of my young adult life: I chose to study math because it was my best subject, got a teaching certificate because that’s the only job I thought a math major could get, and went to graduate school to open more doors and earn more money. But also at each step, I was riddled with doubt over my choices and needed to convince myself that “most practical” meant best.

After struggling for years with depression, anxiety, and feelings of inadequacy, I sought out resources to help me to challenge and reevaluate my philosophy on life. What I found not only showed me that it’s okay to not force myself onto the most practical path, but that was also more timely than I ever could have imagined. I’d been introduced to The Tao of Pooh, a book using the characters from A. A. Milne’s Winnie-the-Pooh to explain how to appreciate and work with whatever happens in life.

This fascinating little book by Benjamin Hoff touches on not only self-acceptance but on issues as large and current as climate change, hustle/overwork culture, and our obsession with the future manifested by making as much money as possible and preventing aging. Most importantly, though, its ideas can easily be applied to modern life.

Let’s consider, first, an idea called the Uncarved Block, which Taoists interpret roughly as “things in their natural state.” Seeing things as they are, rather than using Cleverness or Knowledge to manipulation them, is an ideal that Pooh epitomizes. Put simply, an appreciation of the Uncarved Block means putting circular pegs into circular holes.

There have been several moments where circular holes opened up in my life: the Spanish classes I enjoyed so much, study abroad opportunities. But instead of pursuing new passions, I stuck to the course I’d mapped out before even entering college. I didn’t understand that reevaluating my likes, dislikes, strengths, and weaknesses — looking at my Self in a mirror — was a worthy effort for the sake of my happiness. I’ve discovered now that my “true nature” is okay, however flawed and scarred, and will make choices that work with what I’ve got.

In a similar vein is an idea called The Great Nothing, again exemplified by Winnie-the-Pooh. Hoff explains that the Empty (i.e., open) mind is valuable because it sees what’s in front of it, as opposed to the Overstuffed mind. He says, “While the Clear mind listens to the bird singing, the Stuffed-Full-of-Knowledge-and-Cleverness mind wonders what kind of bird is singing.”

Hoff then reflects on an important thought: “Many people are afraid of Emptiness, however, because it reminds them of Loneliness.” As a result, we tend to fill in the emptiness in our lives by filling our schedules, turning on the TV, and constantly surrounding ourselves with other people. Taoists believe the removing things from the mind, becoming a child again, is the way to attain Wisdom. Pooh says it perfectly here:

“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.”

In modern life, the Great Nothing isn’t about forgetting or ignoring, but stripping away the clutter that Knowledge and Ideas amass. For example, we view global crises like climate change as political issues, when in reality, we should strip away politics and view climate change as it is: the devastating effects of the actions of humankind as a whole.

The last idea I’ll mention stresses the importance of not only the destination, but also the journey. Hoff refers to those in opposition with this idea as Bisy Backsons, named in reference to a note Christopher Robin leaves for his friends, which says “BISY BACKSON” (busy, back soon). Backsons come in many forms, with one example being those who push themselves to the max for “physical fitness,” so much so that exercise becomes work. Backsons are looking to find something out of reach, thinking that “working like lunatics,” as Hoff says, is the only way people can get there.

Devoting every ounce of energy to reaching the next level leaves a person without time to enjoy a walk in the park or read a nice book under a tree. Taking the time to appreciate what is in our lives is just as important as getting a promotion or being in perfect physical shape. Taking stock of what’s good in our lives now can bring happiness that can carry us into the future.

We all have a lot to learn about appreciating, learning from, and working with the happenings of our everyday lives. Returning to a child-like view of the world isn’t easy, especially with obligations constantly hounding, but looking at things as they are rather than how we think they are, including ourselves, is a good start. Being excited by the small wonders of the day, stripping away our need for more than what’s there, and taking time to appreciate our own strengths are steps in the right direction. Winnie-the-Pooh is the hero of his stories, and by embracing the natural state of things, we can be the hero of ours.

Lindsey Hiltner is a writer, thinker, and dweller-on of topics in philosophy, personal growth, self, and others. She graduated with a PhD in math in 2018 from the University of Minnesota. Find her at lindseyhiltner.com.

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Lindsey Hiltner
The Startup

Lindsey is a writer, thinker, and dweller on topics in philosophy, self, and others. She also has a PhD in math. Find her at lindseyhiltner.com.