When Should You Sell Options?
I had an interesting conversation with an executive yesterday. We got talking about his stock options, and when he should sell them.
I started in the usual place, talking about time value and strike value of the things, with the usual volatility/cliff issues. He kept coming up with reasons why he should sell, despite the stock trending up, despite good numbers, etc. I said, fine, then sell. But, he said, then I miss the time-related upside in the options.
Sigh. You can't have it both ways, I pointed out. And if you really like the stock, then hold the stock after exercising rather than immediately selling it.
But that would be risky, he said, neatly ignoring that he should be indifferent about the risk if he is willing to hold the unexercised options.
Anyone else run into people like his? I'm always amazed at how emotionally messed up some people -- including executives -- get about stock options.









