I’ve been asked to share my option selling strategy. I am NOT an expert. I’ve learned through many years of trial and error, and I think I’ve developed a good strategy. In a nut shell, it is "go for nickles, not dollars." I have a good size account, so I have a lot of shares for covered calls, and a lot of margin for writing Puts. My Realized gain so far this year is almost $2.2m, losses $327,000 ish, for a Net gain so far of around $1.9m. I’ve been trying this for about 5 years, and it didn’t go well in the beginning. I have a few rules I try to live by now that seem to be working. Rule #1 is don’t get greedy. If you look at the options chain for Puts expiring in a month, you will obviously notice that you make A LOT more money selling Puts that are closer to the current SP. I used to get sucked in with positive thinking. If contracts 10% below the current SP are getting X, and contracts 5% below are getting 5X, I used to get sucked in to the riskier Puts (because there is NO WAY the SP is going to go down more than 5% with all the good Tesla news, Right?.… WRONG!!!) I have become more disciplined. I also use the margin calculator tools, and use both the hypothetical transactions tool and the Price Change Tool to see what happens to my margin with a trade, and what happens to my margin if the stock drops a lot more than I expect it to. A margin call at the wrong time will devastate your account. Therefore, Rules 2 and 3 are also: DON’T GET GREEDY, and don’t get anywhere near your margin limit.
Rule 4 is don’t put all you eggs in one basket. As good as a trade looks today, the SP can really drop or climb much faster than you think possible, and ruin everything. A strategy I TRY to use is a revolving door, where I sell contracts a month out, and they are spaced one to two weeks apart. Usually, if you look at how much a contract will net you at a certain strike price, you make the same amount per week if you go out 2 weeks, 4 weeks, or 6 weeks. So you usually don’t gain anything doing half as many trades by going 2x farther out, except more risk if the SP starts to go in the wrong direction, because there is more time for your contract to end up in the money. The exception to this rule is around earnings. I recently sold more 650 Puts and November 19th was paying out better, so I just went out two months. I usually don’t do this, and hopefully it doesn’t backfire. But part of my thinking was that the SP has been way too low all summer, and I expect Q3 earnings to be a blow out. After that, the 650 strikes I sold will be worth very little, so I collected an extra month of premium early on the 650s.
Rule 5: Don’t be afraid to admit you made a mistake, and do take a small loss to fix it before it turns into a big loss. Unless you have a crystal ball, you will have some losses and that’s ok.
Rule 6: Don’t panic if you have the margin. I sold 750 strike Puts around March/April before the SP dropped. I was able to roll them to 700s. Those 700s were in the money for months, but as long as the value is significantly larger than the price gap between the current share price and the strike price, they probably won’t get assigned (but always have plenty of margin in case they do). When the gap starts to shrink with time value decay, decreasing volatility, etc. (usually 1-2 weeks from expiration), roll them out another month. Don’t wait too long to roll. I was making $1,500 a month/ per contract, just by rolling the 700s that were In-The-Money, and they didn’t get assigned even when the SP went to 580 because they were always worth more than the $120/share gap (in the 580 example).
Rule 7: Don’t think everything has to expire worthless before you sell another set. If there is a week left, and I can harvest 90% of the money, I will buy them back with a 90% profit and sell again another month out. If I have enough margin, and the current stock price is well above the strike price, I may gamble a little and sell the new set without buying back the previous ones. This obviously puts a larger strain on the Margin, so I watch carefully and I’m ready to buy them back if the SP starts to move in the wrong direction. It is a little bit of a gamble, because I am risking some of that 90% profit I had locked in, in the hope of pocketing that last 10%. Many times, that risk isn’t worth it (See rules 1-3).
I currently have Puts with 620 and 700 strike expiring 9/24 that are up around 90%. I have November 1 620s, and November 19 650s. There is an October gap because the Nov. 19s were so good when I sold them (that I kept selling more as my revolving door came around - if that makes sense). I may buy back the 700s with a few days left next week, and sell 700s for October 22nd to fill my expiration date gaps. The 700s are ones that I have the cash ready for assignment, so I can turn around and sell covered calls instead.
In my mother’s account, I have Oct 1st, Oct 22nd, and Nov. 19th 620 strike Puts.
Speaking of covered calls (CC), those scare me the most. I have 820s expiring 9/24. After that, I am not selling any more until I see Q3 results. If Q3 numbers look good, I will wait until the SP has climbed (maybe 10%?) before selling new CC. I would be fine selling all my shares at 1500, so I will sell Jan 2023 1500s if they climb back to $70 or so. Otherwise I will continue to sell 2-4 weeks out, and use strikes at least 10% above the current SP. I make a lot less per contract with my CC than my Puts, because I really don’t want my shares called away (so I use a bigger gap between the current SP and CC strike price, then the current SP and Put strike price), but I’m ok with picking up more cheap shares if my Puts do get assigned.
Here is the bottom line. I've been on TMC for 8 years. I haven't seen a single person who can predict the SP accurately one month from now. I think if you are going to sell Options successfully long term, you should try to hit "singles" and use strikes that have very little chance of ending up in the money. I think if your goal is to make 10% of your portfolio value/year using the value of your shares, you are probably following rules 1-3. Some may say 10% isn’t very good, but we are talking about making money on your shares that may not be increasing in value all year because the SP is just trading up and down in a narrow range. This is a strategy for the more conservative Buy and Hold crowd to make a little extra money by being the “House,” instead of gambling by buying options that will probably expire worthless. If there is a SAFE, get rich quick strategy SELLING options, I don't know it.