I don't know how much experience you both have with options, but IV is already at a rather high level of 74.
Everythings relative I suppose... it's spent roughly 12 of the last 40 weeks at/above 90... and about half those 12 weeks above 100... a peak of 156.8 in mid march, but additional 120+ peaks in July and two of em in September.
The main problem I see with options is it is like playing black jack in Vegas. The house wins most of the time.
That's the upside to selling options- if your concern is the house usually wins, be the house.
That said- I did want to follow up on this from last week-
Well- Even if I let them get assigned as-is I'd still be up a fair bit, net, in recent months from the collective profits on all the times they didn't exercise... rolling em up a bit further just enhances that net profit number a bit more.
Higher SP (if it holds up- remember we were in the 460s monday too and dipped down to the 430s later) just means I'd roll it higher.
Ouch! I commend you for remaining stoic.
So in the end I concluded not only had it overshot my sold call target for the week more than expected, it was going considerably higher going forward short term (at the start of the week I'd expected the surge to wait for NEXT Monday after the S&P inclusion details were to be announced 11-30, but nobody's perfect.)
Based on that conclusion I bought back the sold calls in one account (which had some tax benefit, and those shares are up ~$85 each over my cost to do so close of today-on top of the thousands made on those shares selling CCs that didn't get near assignment in the last few months)- so that worked out ok even if I "gave back" a small fraction of my selling-calls profits.
In another (tax-free) account I had 5 sold calls that I let get assigned instead rather than roll... with most of the cash from that at open Monday I bought 32 January 15 $500 strike calls.
Those are up about $115,000 at close today... (on top of the thousands made in recent months on the unassigned calls I'd sold on them), and I certainly expect them to go...at least somewhat higher...before I get rid of em. Mondays inclusion details should impact that though so we'll see how long I keep them- the ideal plan of course it the same I suspect lots of folks have- sell em at the inclusion spike peak, maybe sell very short-term puts with the cash for a few more bucks depending on timing, then get back into shares (ideally via either puts exercising for discounted shares- or if there's a post-inclusion dip)- if all goes well I'll end up with more shares than I started with at higher value, plus maybe a few free LEAPs or something- or ya know I just screw the timing of all of it up... we'll see.
If I'd rebought those calls I'd only be up, net, about 23k or so. Or only about 45k if I'd never sold the calls that got assigned anyway.
So that worked out alright too.
I'd kind of been planning moving a minority of shares over to Jan or Feb calls anyway, getting assigned just got me doing it a week earlier.
Some entirely not-advice-train-of-thoughting here.... but if you're generally selling realistically OTM CCs for months and making nice if modest regular income and not getting exercised as the stock doesn't move up much... and suddenly it shoots way past your sold strike in short order... it might be a good time to look at if getting back in with short(ish) calls makes more sense that shares for some period of time right after.
