Mike Bloomberg, the billionaire business information mogul and two-term mayor of New York City, is said to be pondering a third term in office. Trouble is, the city's mayors are limited to two terms by law. Now, as The New York Times reports that Bloomberg is thinking about asking voters to drop the term limits rule and elect him to a third term. Some corporate business leaders have encouraged him to pursue this strategy "arguing that he towers over the potential rivals," the Times reports.

To me what is fascinating with this story is that it reflects the mayor's entrepreneurial nature. Like so many people who start successful businesses, he is having a hard time letting go of the organization he has built up. He doesn't trust another person to take over for him. He is not comfortable with the idea that a successor will have to learn, over a period of time, about the operation he has painstakingly put together, and how to run it effectively. (He may also not like the idea that someone would choose to do things very differently.)

The Times also reports that Bloomberg's top aides are actively encouraging him not to seek a third term. They worry that his burnt-out staff will quit, leaving his team sapped of creative energy and experience. They also argue that his posture would be undemocratic and could blow up in Bloomberg's face—he's had two great terms, why risk another four years that could be full of headaches?

Bloomberg, of course, has an entrepreneur's optimism and confidence so I doubt these arguments would hold much sway with him. He's probably focused on whether or not the risk of going after a third term is worth the cost to his clout and reputation should he fail. (Losing elections is a strange business. It empowers some politicians, such as Hillary Clinton, but diminishes others, such as Rudy Giuliani.)

So what do you think? Should Bloomberg run for a third term, or is eight years more than enough time for a mayor to make his mark? And what do you think his quandary says about entrepreneurial thinking when it comes to succession? Emotionally, are you prepared to someday step down at your company? What are the pros and cons of letting go?