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Everything I Need To Know About Being an Entrepreneur, I’ve Learned From Winnie The Pooh

Everything I Need To Know About Being an Entrepreneur, I’ve Learned From Winnie The Pooh

You know who would have made a great entrepreneur?  Winnie The Pooh! Pooh and his friends in the 100 Acre Wood were full of advice that can easily be applied to the most difficult of business situations. Those fictitious characters of A.A. Milne not only lived life to the fullest, they shared their struggles and pains within their team and helped make each other stronger. Here are some of my favorites!

“You are braver than you believe, stronger than you seem, and smarter than you think.”

Lesson Learned: The moment you start believing in yourself, there is nothing that you cannot achieve. In my early days of entrepreneurship, I was often almost apologetic for being in business for myself, thinking that someone like me, a young mother who was trying to find balance between baby bottles and board rooms, could not possibly add value in the entrepreneurial community. Flash forward 14 years, and I realize it was those early years and experiences that helped me know that I am strong, smart and important!

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

Lesson Learned:  There is a time to wait and then there comes a time to take action. In business, waiting can be poisonous. One of the privileges of being in business for yourself is the ability to take action quickly. Small business owners can change their course much faster than a larger company because they are not carrying all that extra weight of employing large staffs or needing multiple levels of approval to make a decision. In my years in business, I have learned that the more frequently we push ourselves to ask the difficult question, or make that uncomfortable phone call, the quicker we are able to accelerate the pace of building the business. Winnie the Pooh knows that entrepreneurs need to be hustling,and pushing forward with enthusiasm and passion to achieve their goals.


“Some people talk to animals. Not many listen though. That’s the problem.”

Lesson Learned:  Listening is an art. The more you listen, the more you understand; the more you understand, the more your perspective widens and the better you perceive. I find that being a good listener is the single most effective way to sell. Despite so many people having a discomfort with sales and being too pushy, I find that if I really actually speak less and listen more, we will attract the clients who we are well-suited to serve and we can help them with more things. There is a mutual respect that develops between me and my best client, because we are both receptive to listening and there has been a compelling reason to work together, either emotionally or financially. Pooh knew it and so does my goldendoodle, Patriot…he is a very good listener. When I have a bad day, Patriot is the first to respond to my cues with extra cuddles and protection for me. Patriot speaks to me too, and I can hear it loud and clear when he is scared or happy or excited.

“You can’t save time. You can only spend it; but you can spend it wisely or foolishly.”

Lesson Learned:  Stay conscious of how you are spending your time. Time is not a renewable resource; once spent, you cannot have it back. So often, entrepreneurs choose to do things themselves because it is cheaper and in turn, they spend boatloads of time on a task that could likely been more efficiently and effectively handled by someone else. On the other hand, money IS a renewable resource. If you spend it poorly, you can make more. If you spend it wisely, you might find that your investment will grow and multiply with minimal effort. Some of the bookkeeping tasks we offer at Reconciled Solutions would be considered repetitive and mundane, and it might not make financial sense for you to pay someone else to do the books. On the other hand, what better task to outsource than the one that can free up your time to focus on the more important and strategic quadrant of being an entrepreneur? Time is non-renewable, after all, and a day spent with a pot of honey and friends in the Hundred Acre Wood might be just the wisest way you could spend it.

“Before beginning a Hunt, it is wise to ask someone what you are looking for before you begin looking for it.”

Lesson Learned:  There’s no such thing as a silly question. I often think the most basic questions are the hardest to answer. Pooh apparently shares my sentiment. Why did you become an entrepreneur? How much money is enough? Why do you do it this way? So many entrepreneurs are young, scrappy and hungry and they don’t always think about what they are hunting for before the hunt begins. Begin with the end in mind – that is a great shared lesson from Winnie The Pooh for the entrepreneurial soul.

Angie Noll
angien@reconciledsolutions.net