If I sell a 6-week covered call, and can let it ride 3-4 weeks before needing to roll, won’t the available rolls be reasonably good at that point (as 2-3 weeks until expiry). Well done isolating that as an additional risk, thanks!!
Yes - they will definitely get better as the time to expiration shrinks. You might find that in 4 weeks (2 weeks to go) you will want/need to roll back out to 6 weeks.
I had a recent call with 7/9 expiration that my rule caused me to roll to 7/16 and then roll to 7/23 the next day. It's a 720 for 7/23 expiration and I'll roll again if necessary. I've grown much more aggressive about early rolls, I think mostly due to my experience this year with going DITM on both sides at different times, and how difficult it was getting those legs back close ATM. I'm slowly creeping back out of my cave
My current, constantly changing, personal rules for rolling:
1) Net credit. Violating this rule is rare and usually part of a larger trade where the other part of the larger trade is for a net credit, and the sum total is a net credit.
2) I want to be as close to expiration day as possible, but this rarely influences my decision to roll; DTE is what it is when I roll.
3) The very best rolls exist while still ITM, but are awfully good while ATM or neat OTM. So I aim to roll when the strike is within $5 of the share price, with DTE influencing whether it's $5 OTM or $5 ITM (still OTM with 1 day to go - I'll let it ride if I think it's likely to stay OTM, and let the time decay melt it down).
4) For choosing the new position:
- add 1-4 weeks, with a preference for less. But sometimes (
@Lycanthrope just gave us an example) where the 2 week roll is a LOT better than the 1 week roll repeated 2 times. Sometimes the 3 or 4 week roll provides that big improvement over the 2 week roll, but its usually the 2 week roll that can improve a lot over the 1 week roll.
- improve the strike as much as possible subject to ...
- collect a large enough credit per additional week to clear my personal hurdle rate (around $3/week).
- as the position gets farther DTE then bias towards maximum strike improvement, and give up clearing the hurdle - staying OTM is too important to avoid a really big move
5) This is the tricky one - also be evaluating whether its better to just plan on assignment and let the position go to expiration.
The mindset for me, now, is that when I need to roll to avoid assignment, then the purpose of the roll is to improve the result when I take assignment. I.e. a $3 credit plus $10 strike improvement for a 1 week roll is almost certainly going to be better than taking assignment without the roll. I'm not selling weeklies worth anything close to $13 so adding a week worth $13 is a no-brainer.
And of course that also buys me time for the shares to reverse and avoid the assignment (which is why I also want to collect the ~$3/week credit at the same time; keeps my weekly income going where I'd like it to be).
I've gotten my account setup so that taking assignment on covered calls is going to be emotionally a lot easier for me. I'm not selling CC against shares any longer, only diagonal spreads using long dated LEAPs to back short dated calls. If the CC strike is high enough then letting them "assign" (meaning that I STC the long dated call and BTC the short dated call, probably on expiration day), will yield a nice profit on both sides. Then with that cash in hand, I evaluate the overall account to decide whether I buy new long dated calls to sell more CC, or keep the cash to sell puts and wait for a pullback to buy more calls / sell more CC.
I am confident that I can emotionally take assignment against a long dated call.
And the mantra / question that I keep asking myself, every time I start to make a decision about an interesting position: "this is for income". Which has so far, almost always, caused me to not do what I was thinking about doing