Reply #6: Exactly.

[morillon]

When I was still doing the stock option thing a few years ago, I'd execute what's called a cashless trade, which is pocketing the difference between the current street price and the strike price of the options. I never held any stock for longer than the few seconds it took for the cashless trade to go through. I paid taxes on the profit at the time of trade.

But that only worked as long as the stock went up in price. When I left the company a few years ago, I forfeited thousands of vested shares that were underwater with no hope of being worth anything for at least ten years, if then.

I'm back working at that company now (yeah, tough economic times can make for strange bedfellows), and they don't do options anymore. I'm glad, 'cause I felt a lot of ambivalence about the whole thing anyway. I loathe the stock market and want nothing to do with it.