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I really like the idea of selling the call options to take advantage of the time value (though it is technically nil). I did call and found out that margin or LOC on stock options is not an option on these options, either from my banks or from eTrade. so any margin account work goes away...

Good points. Looks like the way I have been playing it so far is not that bad, which is getting rid of 15% every year. I do have more than 0.5M centered on it still though, which is 70% of my portfolio. In the last one year, the great difference is my level of understanding. And if anything and...

Totally agreed. I have been commiting that crime on time premium for lack of knowledge so far. ITM close out makes sense as well.

Just to make it educational for anyone reading this: I called eTrade and looks like my options on NFLX options are limited. Writing naked calls (which will lock up cash purchasing power and hence a 'no' from me) and exercising and holding by paying for the tax/price are two best options. Not...

Good thinking @ironchef . Let me call my banks.

That would have been the best method. But they don't allow that. The treatment on employee stock options is that it is coupon to exercise/sell or exercise/hold. Nothing more.

I will have to let go of at least 150 options to keep an additional 100 shares. Yes, if I can keep them all, that seems like the best option. I am still reading your reply, some of it is my knowledge gap.

Thank you, I will check that out as well. I have level 3. Doing it without the taxable event seems like an attractive option. Let me check with them.

Any thoughts? Good, bad? Any right strike price idea for the call and put side or What do I need to read/listen to come up with that price. Good thing is that my position size and timing is pretty much decided.

After reading more about collar and calling my broker, the following seems to be my best option: Exercise&Sell enough options to Exercise&hold shares in the multiple of hundreds. And then write coveredCall and buy protective puts (which is what I understand collar is).

It did, thank you. It did give me an option to consider certain options (:)) which I otherwise won't have. But, I have to confess that I did not always manage it well. But, even with the better knowledge I have, I am still not sure if I am doing the right things and hence I am here. On your...

Would be great if you can eloborate on how it would change. Any of what you say might help me in having a better discussion with my tax accountant. He is good but not sure will cover all the bases if I don't ask the right questions. And @ironchef was very accurate when he said that it is taxed...

I cannot write covered calls as I don't own the stocks, just the options. I checked with ETrade. I don't have that much liquid cash to write naked calls.

Mistake, expiring in 2021 and 2022. @newwurldmn ,The strike price is whatever it was in 2011 and 2012. @ironchef , let me read a bit more about no cost collar. Thank you!

added the third point to the main post: Why not off-load all now? I get heavily taxed as I still work in technology at least till this year. 2nd, these are non-qualified options, meaning that tax is part of its growth, until sold. 3rd, there is amazing amount of time value left (4 years in most...

Hi All, First, thanks a bunch for all the great minds in making this a great place to get good education. Bear with me as I go about explaining my situation. Financial planners (who say sell all), nor day traders (whose focus is making money with volatility) understand this fully. My...

Got it, thanks @ironchef.

Agreed!!

Thanks for replies. @ironchef: no blackout dates, since I left them. I still need to call for restrictions, though my guess is, none. Question: if I sell calls, won't I be assigned at any time it is OTM? What if that time is not a time I want to sell, due to tax reasons I mentioned. The answer...