Bird in the hand is worth two in the bush. I know that in the fog of war, it's easy to get fixated on what could be vs. what you actually have NOW. About 3 ye

Bird in the hand is worth two in the bush. I know that in the fog of war, it's easy to get fixated on what could be vs. what you actually have NOW. About 3 years ago I was holding a very large amount of stock in a startup. The primary investor and ceo offered to do some of the early employees a solid by allowing the primary investor to purchase some shares directly from the employees. I decided to sell about 10% which gave me a nice payday, but I decided to hold onto the remainder because 'it could be worth so much more.' Needless to say I'm sitting on some stock that is virtually worthless. While the company in question is still active and doing ok, the real value has dropped, there is no IPO in sight, no secondary market sales opportunity, and the long term prognosis isn't great. If I'd only had asked myself that question then, I would have sold at least 60% or more.