"The toughest question there is"

is to know when to quit - says the serial entrepreneur, Dean Kamen of Segway fame.

I could not agree more. I spent almost 3 years asking that question in a start-up I did earlier in the decade.

I felt obligated to our investors. I felt obligated to the employees who kept trying to make it work. I felt obligated to chase after every hope there was in a new customer or funding or merger opportunity.

But my family suffered. Our net worth suffered. My health suffered.

In the end, my co-founder was right when he left almost 2 years prior. I am sure he asked himself the the same question differently - did he quit too soon?

In this recession, many an entrepreneur will ask the same question. It's a lonely decision. I just hope you don't agonize for 3 years making it.       

Update: Of course, I would be remiss to not point out that Mr. Never Quit, Rickey Henderson just got voted in to the Baseball Hall of Fame. And in an encouragement to many entrepreneurs, Jim Rice finally made it to the Hall also - on his 15th attempt