I have a friend who is a very successful entrepreneur, so successful that at 24 he is the youngest CEO listed in the 2009 Inc 500 (a listing of the 500 fastest growing, privately held companies in the country). He is the person who instilled in me that entrepreneurship isn’t about what you are doing, it’s about the fact that you are doing it. (Something that I also wrote about in Entrepreneurship: Just Do It). This phrase is something that I have really taken to heart, and as a result I’ve gotten the ball rolling on multiple projects. But I want to add something crucial to the phrase: entrepreneurship isn’t about what you are doing, it’s about the fact that you are doing it and having fun.

Having fun may very well be the most crucial aspect in the entrepreneurial process, because if you aren’t having fun you won’t stick with something long enough to see where it can go. The following examples are all people who started out by playing around, tinkering, experimenting, and flat out having fun.

In Steve Wozniak’s autobiography iWoz, he writes about how everything he did in inventing the personal computer was fun for him. He recalls how much fun it was when he played a game where he would try to design a computer using one less chip than he used the time before. Each time he would come up with a more creative way to accomplish his goal. To me that seems impossible, but to him it was playing around. Steve Jobs was the same way, he didn’t have a solid grasp on the engineering side of things, but running the business was his playground.

Michael Dell always loved computers, he loved them so much that he started making them for friends and family. By the time he knew it, he was running a successful business out of his dorm room at the University of Texas…and he was having fun doing it.

My friend in the Inc 500 started out experimenting to see if he could leverage a house he bought to buy another in order to rent it to his fraternity brothers. He had so much fun in the process that it spiraled out of control and by the time he graduated college he was running a $2 million business.

My wife Mary loves to bake, she describes it as her labor of love. She looks forward to playing in the kitchen, baking for our local farmers market, and we both have fun doing a great deal of work to fulfill some orders that we now have from stores. We are by no means a successful business, but we are having fun doing it and making some extra money and for the time being that’s good enough for us.

Another friend of mine, Chris Anderson, combined the three things he loved to play with: wakeboarding, fluid dynamics, and working with his hands; into literally building a best in class wakeboarding boat in his driveway (article)and founding Epic Boats. In fact, he had so much fun doing that, after he found a manufacturing plant for the boats, he wanted to get his hands dirty again, so he started playing with aero dynamics and working with his hands again. This time around his play turned into one of the hottest electric car companies around: Aptera.

Too often we think of entrepreneurs as huge risk takers, but I hope that by looking at the few examples above you realize that often times they aren’t. In many instances it is just someone tinkering and playing around while having fun. When they finally look up they realize they have something great. That’s how Apple, Dell, Epic Boats, Aptera, our struggling bakery, a successful real estate venture, and even this website came to be.

What are you waiting for? Start playing.