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Long post. Bear with me as I try to accurately capture my situation. I have netflix employee stock options that I want to sell over the next 5 years. Not at the same time to avoid too much of short term tax (they are considered regular income as I generally exercise and sell on the same day). Now, there are several ways of doing this from my knowledge on options which I am gathering last year or two, though with minimal actual option-trading experience. But, still not sure what is the best course of action and hence I am posting this here. I don't own the stocks and hence covered calls are out of question if someone is thinking that. This is purely a optimal protection strategy. The possibilities are (assume 100,000 in the current market value minus cost for ease of calculations): 1. I buy put options covering 20% of the options till Jan 18 as insurance and exercise the call options (ESOP) and the put options if they are in the money. Now, these put options can also be of different kind. 1a. Pay 18 USD (as of 04/24/17) for 150 usd strike price (let us assume that 2 contracts will protect 20 % of the stock options) 2a. Pay 10 USD for 135 usd strike price. This is one thing I came up with in terms of insurance as an example. What are the other methods through which I can protect my ESOP (employee call options that have a longer time horizon), if I don't want to sell them all at once? Sorry about the long question, but hopefully I made it clear. If you are clear about his question and have a great knowledge and want to help, I appreciate a direct message as well. Thanks a bunch in advance. One thing I realized is that even if this protects the 20%, there is no quarantee that stock price will stay the same and hence I am exposing the remaining 80% for the next 4 years. May be I am overthinking this...I am sure you guys will set my brain straight.