Here's ALL you need to know about your company stock options: ask yourself - if I had ($PRICE_PER_SHARE * $NUMBER_OF_SHARES) in cash sitting in my checking account RIGHT NOW, would I dump ALL of it into my company's stock? If the answer is yes - hold onto those options and simply DO NOT exercise them. If the answer is NO - FUCKING SELL THEM NOW! Take the tax hit, diversify into other investments, take a cruse, waste it on strippers & blow in Las Vegas - whatever. At NO point hold actual SHARES of your company stock. Options are compensation lottery tickets. That's exactly how executives view them, that's exactly how you should view them. Trust the guy who "held on" to about $100,000.00 USD worth of options as the stock crashed into the ground between February 2000 and October 2000. I could have paid off $40k worth of my wife's & my student loans, $20K worth of auto loans and still had money in the bank after taxes, but I believe the bullshit & hype. I regret it to this day and I'll probably never get type of stock option shot again.

It's a simple question: if I had the value of my company stock in cold, hard ca$h today - would I dump it ALL into a brokerage account to buy said company stock?