• Focus. Pursuing new ideas to the detriment of the core business. ?
• Work/Life. Missing out on real life while pursuing business passion. ?
  
• Employees. Inability to find great help and keep them.?
  
• Partners. Challenges in finding or maintaining good business partners. 
  
• Money. Inability to find necessary financing for growth or survival. ?
  
• Burnout. When one morning you just can’t do it anymore.
  
• Boredom. When there’s not much more to build.
  

We talked about burnout in the last column. In this, the last of this series, we cover what happens when interest level in the business wanes. This is different from burnout, which occurs from simple exhaustion. Here, you may not be tired, but the business may have gotten to a point where your focus goes elsewhere. This is also different from the focus issue described earlier. Here we are talking about simple lack of interest even where a new idea may exist.

The most common cause of boredom is when a business grows to where it becomes harder to consider it “entrepreneurial.” More bureaucracy and formality creep in, multiple layers of management lead to way too many committees, meetings, and the like. This can be unbearable for the entrepreneur who is used to simply diving into something new. Often MEGO (my eyes glaze over) sets in as the founder sits in meetings listening to well-intentioned employees drone on about concerns and risks associated with whatever the issue is.

My moment actually came recently when my law firm had hit over 30 people and we had to prepare our first employee handbook. It is true we needed it. But the multiple rounds of drafting, and the one colleague who would not sign the acknowledgement because she was reviewing it with her lawyer, made me realize this was the very type of “bigger company” event that caused me to pass the Managing Partner role in my firm on tto another partner, leaving me as “Founding Partner,” to be bothered only for truly major decisions.

So what should you do when you become bored? Some of the solutions are similar to those for burnout. For example, you can choose to sell the business, or put someone else in charge while you pursue something else.

But are you sure you will be able to avoid worrying about everything and micromanaging? In my case I admit I am not sure.

How do entrepreneurs who start something small and keep building to millions or even billions of dollars avoid the boredom that follows the business's institutionalization? These entrepreneurs fit one of two categories. Some love the excitement of “the deal,” like Sanford (Sandy) Weill, former head of Citigroup. What got him excited every morning was the next big acquisition. These types, which I believe also would include media mogul Rupert Murdoch, are also driven by the “size matters” school of success, and what drives them is the need to constantly make the enterprise larger. They particularly enjoy the ego boost of being in charge of such a large and prominent enterprise.

There are others, like Bill Gates of Microsoft, who appear to have a visceral need to control everything around them. If Bill cannot acquire it, he wants to control it some other way. If he cannot control it, he needs to try to crush it. I think to this day it drives him nuts that, even though Microsoft is vastly larger than Apple, he was not able to make the Cupertino company go away. Controversial media personality Howard Stern says, basically, I cannot rest until every single radio listener tunes in to me and no one else. This extreme competitiveness allows these moguls to rise past the boredom phase and leave day-to-day matters to others while they search for the next thing in their way to be taken or destroyed.

As this series has been all about regrets, I would like to end on a positive note. I think most entrepreneurs believe that dealing with all the challenges and laments in their way are almost always worth it in order to have the freedom to pursue business opportunities unfettered by infrastructure, bosses, and in many cases even partners. It’s as much about the joy of that freedom as it is about the ambition for financial success. I have many regrets, in the sense that there are certainly things I would have done differently in my various entrepreneurial endeavors. But I have no regret about choosing the path I did, and I think almost all entrepreneurs will tell you the same, gray hair notwithstanding.

Look for a new series focusing on entrepreneurship next….