I was thinking of looking into some longer term calls to sell on top of the weekly selling I'm currently doing. Lets say I don't have the full amount of shares to cover this call, for argument sake lets say 50 of the 100 shares to cover 1 call. Would this be unadvisable? Also, If I did have enough shares to cover both calls (the weekly, and monthly) would this be a strategy people utilize? a short term sold call and a longer term sold call.
Advisability aside (something we each decide for ourselves), I do have some observations about long term calls (a 1 year and a 2 year that I've sold).
First up - you'll have to use margin for an uncovered call (or a lower strike call as you note). You'll have to decide for yourself your comfort using margin - I wouldn't personally do that, but I'm growing increasingly risk averse (for my definition - financial advisors still think I'm comfortable having my hair on fire
).
If you go for a call as your backing, then that sounds like a calendar spread (probably a long expiration, deep ITM long call paired up with a series of shorter term OTM short calls). I've read about this, but don't really know beans. And no experience. I got nothing on this.
But selling long term options - I do have some observations. I sold some 1 year covered puts back in Sept and some 2 year covered calls back in Sept.
In both cases, those very long dated positions have left the accounts feeling like they're trapped in amber. There are shorter term trades I want to be making and don't have access to.
I try to remember that I generated $120 contract premium for the calls which works out to $5/month, every month, for 2 years. At least for me, that is a really good outcome. Except now I have that cash I can do a little bit with, but the shares are all covered, and those covering calls have a LOT of time value in them (over $300). So I get to sit and watch for most of a year and a half while the time value shrinks to 0 (deeply ITM, or close to the strike, near expiration).
My learning from that - I won't be selling 2 year options again.
On the plus side - if you're going to hold the shares for the period regardless and you'd be happy with some selling at some ridiculously high strike, then you can generate income today that works out to a good monthly result for the entire period, with no need to manage. As somebody that has sold a 2 year 840 call down in the 300s, the overall result will be great (3x value when the position resolves). I keep telling myself that - it's still not feeling so great right now (where not so great is still +50% to "enough" for retirement; no violins necessary).
I also sold some long dated puts, good for $20/month premium with a 1 year expiration. Same dynamic as the calls - these were cash secured (no margin here for flexibility) and locked up a bunch of cash. The difference is that with the radical run, the value of the puts dropped a lot and I was able to close early for about 2/3rds gains (2/3rds gain in 1/3rd of the time - me like).
But same learning - I won't go out a year again (at least not if I can avoid it).
I've traded weeklies and monthlies. I didn't like the monthlies dynamic (time decay too slow early on, and too much time between opportunities to reset the strike for my taste). I don't like the 3-8 day option sales - good premium and income, but needs pretty much daily tending.
I've evolved, for now, to lining up my options on every other weekly expiration. So I'm rolling out of Jan 22 options (done) right now into Feb 5 options. In today's instance, I'm not using the Jan 29's at all. As a bonus, the only roll I've done so far using a 2 week option had MUCH better roll choices available than the same roll for 1 week ($5 strike improve vs. $30 strike improve, about the same minimal net credit).
And as the Feb 5's start rolling, they'll go out to Feb 19. This is mostly a sanity exercise for me - fewer positions to monitor, and fewer expirations.