Couple of questions before we get to other things. What delta / % OTM do you write options ?
I used to use .16. I've evolved to the point that I mostly don't look at delta / %POP / %OTM - its more of a feel thing. That being said I prefer the emotions from being further OTM (.08 to .13 delta?) over the higher premiums from being closer.
Sounds like a good plan. So, if the SP goes against you and comes close to strike (say with 1% or 2%), you would roll it. In this week's example, would you roll 220 calls on Thursday when we can to 218 / 217 or even 215 ?
In the specific instance of 220 calls and my situation, yes. For me I've got shares that selling at 250 would be just fine. But selling at 220 - its well worth rolling at least to 250 before letting them go, so I'd roll those really early at a hint of challenge. Probably not as early as 215, but definitely 218-219. Of course later as well, but I prefer rolling while still a bit OTM.
As a different example I had 200 strike puts expiring this Friday. They were ITM early / mid week and I didn't consider rolling them, even for a moment. In their case I wanted to buy shares at $200 if they were offered, and I'd accept the put premium as income for that opportunity. Shares could have fallen to $160 and I wouldn't have attempted a roll - just take the shares.
So a big part of my roll decision making is how close I am to my guard rails. I've got $200 as a particularly low share price, so I've got a bias towards selling puts when the share price is in that neighborhood AND a bias against selling calls. Similar for $250 - a bias towards selling calls, and away from selling puts. Here at $225 might be an ideal time for selling both (in my trading 'plan'). Whether puts or calls I would have a strong bias towards an early and aggressive roll, as I'd be trying to get my strike out to a guard rail before getting run over.
As a for-instance, and not-advice
First off - I'm only selling options that are fully cash backed. That means csp and fully owned (not margined) shares. I AM buying leaps but those are a 6-18 month capital appreciation play to augment the income generation. My income is a lot lower today than a couple of years ago. Interestingly I sleep just as well (might say something about me). And I know I'm taking on dramatically less risk.
Here at 220 ish, if we open flat on Monday (so I can use the weekend option chain), I like the 205 for this Friday, and probably 195 for a week from Friday. These would be CSP - I'm not confident enough yet for BPS, though I continue to evaluate the opportunity. BPS would be particularly appropriate if the share price gets particularly low. I would sell 1 of the 2 CSP on Monday and then sell the other one as early as Tuesday if the share price is down.
On the call side - I think the 235 for this Friday would be my choice, and not touching the following Friday (too little premium, and I can't get as far back from the share price as I'd like. This is the side I would be most worried about, and would be rolling by 1 or 2 weeks if the share price were over 230 even if that happened on Tuesday.
And I don't bother evaluating call spreads - they might work really well, but I'm an emotional wreck while these are open, so I just don't bother. That mostly means that I don't do IC.
My own situation - I'm in the neighborhood of 75% cash when I'd rather be 50% at this share price. So I'm looking to buy, and is another influence in how I am presently treating calls and puts. Though I'm ok selling at 250, I don't presently has as much exposure to the upside as I'd like so selling it off is really unpalatable. Very strong bias right now to buy, yet still somehow being patient for where I want to buy (sure hope I'm right).
Yes - but what do you do - say when you sell a call on Monday and on Tuesday SP has gone up already ? Do you roll or .... wait and roll the dice?
See above, but the decision will include these other factors that matter to me. So if I sold the 235 call for this Friday, and then the shares moved up to 230, then I'd be very likely to roll that immediately for as much strike improvement as I could get - ideally 250, but maybe only 245.
On the other side - if I sold the 205 and then later that day we were trading at 207 I'm pretty sure I'd do nothing AND not be worried about it. Not because I expect it to finish OTM but because I sort of want it to be ITM (so I get the shares).
The call side decision making - that's because I don't have shares I'd be happy selling at 235 AND I don't like sitting out all the time on the call side. If the share price is flat to down then I'll be earning from the 235s. But if the share price goes up then I'll just go a few weeks without cc income - which I'll be doing anyway if I'm not in.
And 235 is close enough to 250 that I can roll there pretty easily. The problem on the call side is if the share price is (for example) 150 and I'm happy to sell at 250. I'm going to be selling more like a 170 or 180, and that's easy to run over on the way back to 200-250. I'm still really stressed about it because I know we can get back to what I consider a reasonable share price and run those calls over badly, and avoiding stress or mental anguish is an important component of my decision making.
In both cases its what I would to happen to the shares at that strike price that also informs my decision making.
This might be a lazy wheel view of things. My trades are primarily focused on income, but they also secondarily consider capital appreciation and I look to swing back and forth between cash and shares. At the sort of premiums I've been getting lately a $20 capital appreciation along side of the income options would be 15 to 20 weeks of income, and a $20 move in the share price isn't all that hard to come by.
With as much insight that we gain through our own sharing, what seems to be safe eventually fails to be. As has been said by many, close on sharp momentum shift, reset with another position or sit out.
As much as I would like to have a mechanical trading system I know that (a) I won't be able to build one and (b) more importantly - if there WERE a mechanical trading system, then somebody else with a lot more money / time / resources would be using it, removing its value.
So anything can go haywire, and we've people get run over in both directions. Anything can go against you. But - its also my belief that my understanding of the company is an important advantage in my trades. It is, if you will, my edge in the market. That, and this thread and the insights being contributed by everybody, all the time.