Think Winnie the Pooh is just a feel-good children’s story? Think again. There’s a lot of business wisdom to be found in the little bear’s quotes.

In honor of Winnie the Pooh Day, marked each year on January 18, I’m going to share some of my favorite sayings from Pooh Bear and his friends.

Winnie the Pooh Day commemorates the birth date of author, A.A. Milne, who wrote his first collection of stories about the very human teddy bear in 1926. Since then, not only have countless children grown up with the books and Disney movies, but the little bear’s quotes have touched adults, too, for their simple wisdom.

In the spirit of Winnie the Pooh Day, here are 7 ways new entrepreneurs can learn from the wisdom of Pooh Bear.

Dream Big – and Believe in Yourself

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

When you are planning a new business venture as a solopreneur it’s easy to be overwhelmed.  A steep learning curve is needed to effectively manage your new business and you can feel like you are constantly learning new skills that your previous employment didn’t ask of you. It’s comfortable repeating what you already know and being a solopreneur well and truly takes you out of that zone. Add to that the perception that ‘everybody’ else seems to have their act together online  … it’s understable if you experience the odd confidence wobble or two.

But, here’s the thing.

If you’re doubting yourself, that’s a good sign.

Business writer, Liz Ryan, says self-doubt is more common among those who are smart and talented. She suggests, among other reasons, that brighter, highly capable people are aware of the limitations of their knowledge and recognise they can never know everything there is to know.

So, when your confidence falters remind yourself of that. You are clearly smarter than you give yourself credit for. And anybody who is ready to launch themselves from their comfort zone to taking full solo responsibility for making or breaking a new business … that’s a pretty courageous act. But, one that will ultimately be worth the discomfort.

As Pooh Bear says:

“When you see someone putting on his Big Boots, you can be pretty sure that an Adventure is going to happen.”

By all means, keep working on your knowledge and skills but don’t let the process of preparing stop you up from implementing your goals. Start, evolve, refine. Repeat.

Or, in the words of Pooh:

“So perhaps the best thing to do is to stop writing Introductions and get on with the book.”

The value of building and fostering relationships

“It’s so much more friendly with two.”

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

“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.”

Let’s say you’ve taken the plunge. You’ve handed in your resignation and you’re ready to do this solo thing.

No more office politics.

No more pointless meetings.

No more peak hour traffic and crowded public transport.

Yep. This is going to be good.


Research shows that  positive relationships with our work colleagues significantly contributes to our well-being. And, that social relationships are essential for our physical and mental health. It’s important that you actively find ways to replace those collegial relationships of the workplace.  How? Consider joining local business networks or online professional communities.

Practise self-care

“A bear, however hard he tries, grows tubby without exercise.”

Okay. I know you don’t need reminding. You know that not looking after yourself can have far more serious health implications than just a tubby-looking belly.

Like heart disease.

Like increased cancer risk.

Like muscle and bone degeneration.

Not to mention that exercise also helps you concentrate and focus, which will help you work much more efficiently.

Do as Pooh suggests and go for a walk. Or two.


What’s your favourite Winnie the Pooh quote? What wisdom does it offer to you?

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