Very helpful. I must be dense or missing something. I don't understand how this strategy works in real life. If the SP keeps increasing, It seems to me that you would always be closing out the CC at a loss. If you are using the premiums collected to purchase additional shares, where does the cash come from to buy back the CC?
By specifically using the Roll transaction type (rather than a buy-to-close transaction plus a sell-to-open transaction). The sell to open generates the cash used in the buy to close transaction. The net credit (or debit - but only roll for a credit ) is what's left over after paying out on the closing side and taking in on the opening side.
The key here, I believe and am testing for myself right now, is don't close too early when you go ITM. In my case, I have a 760c expiring this week. It still has $9-13 in time value today, so even when it was $12 ITM earlier this morning I never considered rolling. There WON'T be an early assignment when there is that much time value remaining (not a guarantee, but I'll take 6 9's or whatever likelihood of no assignment). And for this roll purpose I'm sort of indifferent (at least in this particular position where I'm trying this out - still learning though) to being $10 or $40 ITM at expiration.
If time value is ~0 when I roll, then I'll have a net credit available when I roll out (a week, a month, whatever) if I leave the strike the same. I can then trade in some of that net credit for a higher / better strike (this is all part of the decision around WHICH position I'm rolling into).
So current example, and something I wanted to post as well. That 760 call for this Friday expiration - it still has ~$10 in time value. Therefore too early to roll. I'll keep an eye on it tomorrow, but my best guess right now is that option is going into Friday. What I'm watching is the time value on the option (mostly anyway). That time value WILL got to 0 at expiration on Friday; somewhere close to that (say $0.50?) I'll roll, whether it's ITM or OTM at that point. I'll roll out to the next week option, and I'll pick a new expiration based on all of the usual stuff that goes into picking a position.
If I'm far enough ITM, then I'll be picking a strike that is closer but possibly still deeply ITM.
The real point today is that I had as much internal angst this morning when I was $10 ITM as I had yesterday when I was $25 OTM, as I do right now ATM. Which is to say - none. Partly that is the size of the position, but mostly is that I believe I can roll this position to avoid selling the shares (if I want to), and keep the weekly credits going at a 'high' level (for the outcomes I seek), potentially indefinitely.
This particular position - I started it on Monday by purchasing 100 shares for $735. That's the shares that provide the cover to the 760 call. My worst case outcome on this position to the upside is that I collected a ~$9 premium plus it goes to expiration and I earn another $25 on the buy-735 / sell-760.
Yes, I would have made more by just buy and hold (assuming the shares go past $770ish). But this is cash that I don't want to buy and hold with - I already have enough shares and in my case, I'm more concerned with cash flow / income than I am with maximizing growth.
And most importantly for my situation, I have downside protection on these shares I bought at $735 - we didn't know on Monday we were going to see $770 later in the week. If the shares had been flat at $735 (or down) then I would be ahead by the $9 premium and I would be able to sell another call for next week using the same backing shares.
I like being paid to learn!
If this isn't yet making sense, then two ideas given that you want to continue at all :
1) keep asking questions (and reading, and doing other study yourself)
2) Setup a minimum position to start learning what those mechanics look like.
In my case, my first one of these , back in April when I started, was to sell the $200 put when shares were at $420 or so. I think it was 2 weeks out - maybe a month. And pre-split numbers too! I wanted to be REALLY far OTM on that first trade. The second trade was the $175 put with shares at $400 (even further OTM).
The real purpose was to start learning, and at least for me - I need some skin in the game to lock in the education. I made money on those two positions (I like being paid to learn).
I also intentionally setup small positions to try out new ideas (new to me anyway) to gain some experience with how these trades evolve, how to set them up, how to close them. That's what this current position is - really small, but hoping to demonstrate to myself that I can be much closer ITM than I have been, thereby earning a higher weekly premium, and still doing it 'safely' (for my context).