Wisdom from the Hundred Acre Wood
Originally a thread on X/Twitter:
True wisdom comes in many forms and I’ve found that one of the most underrated sources of wisdom is children’s books. The best are pure, simple and true.
What follows are personal learnings based on quotes from one of the greatest prophets of all time: A. A. Milne.
“You’re braver than you believe, stronger than you seem and smarter than you think.” – Christopher Robin
I find this quote great to remember when I’m having one of those days when up seems down and left seems right. It encourages me to stay the course.
“They have no imagination. A tail is just a tail to them, just a little something extra in the back.” – Pooh
Finding flaws is easy, mechanical and at times very depressing. Living in the art of the possible is where magic is made and honestly more fun.
“The most wonderful thing about Tiggers is, I’m the only one.” – Tigger
It’s taken me 51 years to embrace the fact that I’m an acquired taste and a unique one at that. I sleep perfectly well at night knowing that it’s OK that I’m not everyone’s cup of tea.
“You can’t stay in your corner of the Forest waiting for others to come to you. You have to go to them sometimes.” – Pooh
It’s easy to become complaisant when you get busy. I remind myself that relationships are a two-way street and require effort to keep strong.
“If possible, try to find a way to come downstairs that doesn’t involve going bump, bump, bump, on the back of your head.” – Pooh
Most problems can be solved in more than one way so I remind myself to always search for solutions that don’t require Tylenol afterwards.
“If the string breaks, then we try another piece of string.” – Owl
So true for startups. Falling in love with a problem is more important than falling in love with a solution because it might take a few tries to get the solution right.
“Could be worse. Not sure how, but it could be.” – Eeyore
Bad news is never easy to deal with but I try to remind myself that being an Eeyore isn’t helpful for more than 2 seconds. Complain, take a deep breath and then go figure things out.
“I must go forward where I have never been instead of backwards where I have.” – Pooh
Experience is valuable but it can be a crutch. Being on the steep part of the learning curve is what I value most in life and it requires constantly moving forward.
“Before beginning a Hunt, it is wise to ask someone what you are looking for before you begin looking for it.” – Pooh
It’s impossible to escape a conversation with me without truing back to “first principles”. It’s served me well and I don’t apologize for it!
“So, they went off together. But wherever they go, and whatever happens to them on the way, in that enchanted place on the top of the Forest, a little boy and his Bear will always be playing.” – A. A. Milne
Reading this makes me want to share Milne’s brilliance. Enjoy!


