Assuming that you diversify into the general market, here are some guidelines. If you have a five-year time horizon, consider selling more than half of your SuperCompany stock. If your time is 10 to 20 years, consider selling most of it. If you sold, you'd have to pay ordinary income taxes. To be prudent, Feld says, you'd still sell at least part of your holdings, and diversify.
Options have a time limit.
You can't keep them forever. If the stock dives, your net worth could blow away. The only difference between selling options now and selling them three years from now is the timing or your tax payment. There's no guarantee that diversifying will be the best choice, every time. But it puts the odds heavily on your side.