I've heard of a situation where people exercised their options at the stock's high point (because of the 90-day limit, or just plain ignorance), but by tax time the stock had dropped precipitously because of an accounting revenue recognition scandal.

Even though they didn't sell their stock at a loss, they were forced to sell a big part of their holdings to meet their tax bill.

But, worst of all, the stock rebounded the next year.

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I had other friends that exercised their stock, knowing full well they'd have to sell some at tax time to pay their taxes. What they didn't count on was getting promoted to the C-Suite and ending up LOCKED OUT of selling stock.

They told me the story of this huge tax bill (which they could have comfortably paid if they could sell), and a huge penalty for paying them late. I'm not a tax person by any means but I suggested they _donate_ stock to charity.

Turns out it was a good idea. With their tax accountant's guidance they were able to donate stock at the current value, realize the deduction and offset their gain. Problem solved.

(Again, I'm _NOT_ an accountant. Don't try this on your own at home. Only attempt in the presence of a qualified tax accountant.)