I also had the exact same situation. Part of your problem is that you have to document a plan of when you sell as I did. So you can't mange market up's and down's with your plan. You could look at the stock history and determine if there are patterns. My recommendation is build your plan to sell a minimum of 50% over the next 6 months, then another 10% of the balance every 3 months going forward. Lock in the gains and diversify. You have all your eggs in a single basket. Forget the taxes, just get yourself to a more flexible position. Take the cash, lock in the profits, move it to simple low cost index funds and remove the risk of a large portfolio in one place. If you retain any, keep the RSU shares.