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I realize there isn't an easy answer to this but does anyone have any general rules or thoughts about when it is a good idea to cash out stock options? Do you wait until they nearly expire? Set a price?
The first set of my husband's options have nearly doubled and we're getting itchy to sell but they don't expire until 2015. He has two other sets of options at greater returns that haven't all vested yet and don't expire until 2020.
It's pretty much free money so sell when you want. But do think of the tax consequences and what it will do to your returns.
And don't forget..what goes up can also go down.
I had stock options when I was working. The first set I did OK with but the second set ended up expiring underwater.
Considering your asking this question now, its already too late. But if you were "thinking" about selling I would have suggested in 2012 BEFORE taxes went up on short term capital gains.
As others said, asking us is useless since we don't know anything about the company. Your husband needs to figure out when he thinks the stock will sell at its highest.
My general rule is: never own stock in the company you work for.
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