But this isn't what we're supposed to do in this thread, right? We're supposed to let the shares get assigned or called away, and then swap puts/calls, right? Why is that so hard?
The good news is that there are many variations of the wheel being practiced by people here. Some are aggressively going back and forth, earning very large premiums per contract compared to writing further OTM options. I mostly like the share and cash positions I have, so I would prefer keeping the premiums and not turning shares into cash; cash into shares.
The way I think about it - The Wheel (turning shares into cash; turning cash back into shares) - is one of my fallback positions to selling options.
I.e. - a covered call goes far enough against me, then one of my choices is to let those shares get sold at the strike price, and use that cash to sell puts.
The ultimate fall back for me is my investment thesis and expectation that Tesla will do really well over the next decade. So at the end of the day, I own extra shares on a put assignment.
As I'm more focused on income these days, then the downside of a big upmove is that I get assigned on covered calls that represent an excellent selling price over when I sold the call. I give up that upside exposure and gain some risk mitigation with the premium I collect.
My primary and first solution to a position that moves ITM against me is to roll that position, typically to a later and better strike than I'm closing.
I expect that each roll will have a few characteristics:
- always for a net credit
- the strike price is at least flat, and ideally moves at least 1 strike closer to ATM
- the net credit is large enough that it's about the same as a new position rather than a roll
That last bullet is a reasonable outcome whenever a rolled position is more aggressive than the original position. I.e. rolling into a .40 delta position, when the .30 delta is more typical.
Lastly - I also believe that they key to getting rolls right consistently is to wait for the time value to be close to 0. That mostly means waiting until the day before or day of expiration before executing the roll. You want to have 'earned' as much of the time value from your original open of the position before you roll - any time value that still remains when you roll is something you have to buy back first (you're giving that away), and the less of that time value you have to buy back the better.
I say time value close to 0, as any position that goes a lot against you (deeply ITM) might see it's time value approach 0 much sooner than expiration.
This dynamic of waiting for time value to be ~0 is something I'm starting to experiment with using the aggressive strangle I'm trying this week for the first time, and plan to be working repeatedly in the weeks to come. If it works as well as I expect it to, then I'll expand the number of contracts somewhat - I don't want to do this with the bulk of the portfolio, but I also don't want to invest the energy if it's trivial. For now I'm in education / experience mode; how much better results, how difficult to manage strong moves (either direction), etc..