Charlie O'Donnell has a great post about letting other people muck around in your stuff to make it better.
I never figured out how to build a machine that ran on its own power. When I graduated, it died, not because there wasn't anyone around willing or capable of picking it up, but because I never made the personal and psychological sacrifices necessary to ensure it would last well beyond my time at Fordham. I never imagined The CBA Business Journal without me. That was a problem. The question is how do you do that? This is one of the most fascinating aspects of the creation of a business from my perspective.
I think it would be interesting to hear from entrepreneurs how they psychologically, especially in their first venture, start letting go of the reins for the greater good of the business and start imagining the business without themselves. When you do you realize you need a CEO? When do you decide to leave a business?
When I sold my stake in my small business, I thought I would miss it tremendously. I loved watching it grow and at first it was very hard to be away. I was surprised how quickly I got over that. I still want to see it be successful, and I still refer people there when given the chance, but I no longer miss the day to day duties I had grown to love. In part, it's because I have lots of other ideas. I think most entrepreneurs are in the same boat. They have more ideas than they have time or money.
It is hard to let go. It is hard to accept when you are no longer the person that your business needs. But if you are bright and resourceful and creative, there will always be a business that needs you, problemably a new one of your own creation.