IIRC, you were selling shorter term CC when you started the Wheel thread. As your experience improved do you have any more thoughts on a generic timeframe?
Around Christmas Eve, I’m also hoping to sell a few CC right on the absolute high of the year (currently predicted to be $845 in my “you must be dreaming” perfect world). My thinking is to take advantage of time decay in that last three month window, thus selling Mar21 or Apr21 1000c instead of Sep21 or even longer Jan22. The premiums are lower, maybe $25-$35, but with a decreased chance of being called away. I would probably do 6 to 9 contracts, thus clearing $15k to $30k if not called. Given Tesla’s 50% yoy growth rate, the $1000 SP could be breached in late 2021, $1500 in 2022, $2000 in 2023. I certainly don’t want to risk losing the shares given that growth rate. I don’t really need the cash now, thus the premiums would probably be plowed back into stock (filling in those pesky non-round lots of 20, 25, 40, 60 shares that I have in various accounts). Decisions.
I do have my own thoughts, from my own experience. That experience has a broad stroke of red in it due to that one expiration day in August with the >$200 move that trading day. I had sold a weekly for that day thinking I would safely nick a few bucks of premium. Single worst trade for me selling options this year - enough bad on it's own to wipe out 4-5 months of trading profits to that point. (I ended that trade positive via roll, and a big drop back in share price, but still).
I learned then, something I keep repeating to myself and then finding a reason to violate, that I don't write ccs unless the strike is one I'm happy to sell at. Larger context - neither I, nor my wife, want to sell at all
. But I'm willing to sell now at enough of a markup that it all works out well overall.
Example of that last - I've sold some Sep '23 840 calls. The shares were around $400 at the time. When I mathed that out, should they be assigned, then we keep a $124 premium AND we sell at a big bump relative to when we started. That big premium provides living expense money now, and if we end up selling at expiration, then the overall portfolio has increased from "enough" to roughly 25% more than "enough", ignoring the changes that would bring to the other accounts ("enough" = scheduled retirement date
).
Thus trading away the possibility of a big move past $840 in 2 years is worthwhile, when I get such a big premium for living expenses in the meantime. And as a bonus, the income from that sale is what I'm using in that account for the purchased calls that are up by a lot.
Because of the first constraint - never sell a CC at a strike I'm not happy to sell at (i.e. - I treat these as pre-sales of shares) - I haven't been very active on the CC side for a few months now.
I HAVE transitioned away from weekly CCs to monthlies though. My rationale includes:
- I want better strikes (further OTM) and I'm willing to accept lower total and % return to get them. For CCs, the strike is my primary concern (more .05 to .10 delta, than .20 to .30 delta as I've been using with puts). Then I look at the premium - I'd like to get $7 per month (yielding $5 for an early close at 2/3rds), but that's negotiable.
- Having worked the weeklies for several months over the summer, I liked the results but I didn't like the amount of attention, energy, and time that was consuming. So I've also been moving put sales to monthlies as well, though if I were working the weeklies (now or in the future), it would be weekly puts and monthly calls. The monthly expirations that are 3-9 weeks out has enabled me to more easily ignore the short term gyrations due to being so far OTM plus having so much time for a move in my direction.
- Among option selling strategies, what I've read pretty consistently suggests that this 20-60 day window for option sales yields optimum overall results. I've seen this in the context of traders that sell options and leave them to expiration (higher volume strategy - they don't put any energy into individual positions along the way). I've seen this in the context of early closer, with higher premiums by starting positions of 1-2 month duration, and then seeing time decay kick in strongly the last 3 weeks.
My own brief experience - it seemed like I could earn more on the weeklies (i.e. 4 weeklies would beat 1 monthly). But the weeklies were a LOT more exposed to a bad move against me. And since I like to sell both puts and calls, anything that works well for me in one direction works badly for me in the other
CONCLUSION: One reason to work the weeklies, at least for a few months, is the increased rate of experience and learning that comes from it. In 5 months of weeklies, I estimate I got most of the experience of 20 months of selling monthlies. That experience is an important component (but not the primary) for scheduling my retirement date. That was really good for me.
Having had that experience though, I prefer the dynamics of the current and next month contracts.
I'm thinking about the same as you on the 12/24 CC position. I'm flexible about the duration, but I've already sold a 2 year CC position once - I'm not shy about doing that again. My guess-of-the-moment is I'll find my best balance around 1 year though (not enough incremental time value for the extra year).