methinks that the 'NEWBIE Trader' sign up there will be staying for a while
I think we're all newbies. I know that I am, and likely to still be in a few more years.
I hope we don't have to wait too long - not sure if my addicted brain can survive very long without the next 'fix'
. Looking forward to getting more insights from your noodling - I have plenty of profitable leaps that are just sitting in my IRA that could benefit. Not sure I would want to do this in my brokerage - the risk of assignment and resulting tax liability is just too high (these are June'22 with 252 strike price -very deep ITM, but don't want to sell and take the profit this year)
My initial thoughts is to take a subset of my shares / leaps, and start selling the aggressive cc's. The idea is to raise the high premiums right now and positions myself to either collect those high premiums and sell at this ATH, or collect those high premiums and watch the shares drop back leaving me with the shares as well. I'd be doing this with something like 1/5th of the leaps / shares as sort of a programmed sale at a high, much as the leaps I own were purchased at a relative low.
Whether I keep those initial shares as well, then I probably take another 1/5th and add them into pile being sold if/when the shares reach $1000.
But I've got a larger setup where this seems to fit well. A brokerage account for living expenses in which I'm also just paying the taxes -- it's a big headwind
Holding onto the shares and leaps is probably what I'll do here - no need to increase the tax bill for this year at this point.
I've got a retirement account that is focused on growth. That means mostly leaps and a lot of put sales - I won't start selling the aggressive cc's while we've just barely hit the ATH - I'll wait for a longer run before I start doing this.
The final account though - it's a rollover IRA that I use as needed (so far that means never) for lumps of cash. I like the idea of doing some targeted sales at relatively good prices, positioning that account to make particularly good use of the shares coming back down.
Is selling $100 spreads, and then shrinking to 2x $50 more profitable than just doing 2x $50 to start?
From my two experiences doing this, no. I think the $100 moving to 2x$50 got me something like 1.25x the premium from just selling the $100 wide spread up front. The 2x $50 wide spreads is probably 1.5-1.75x the premium from the $100 wide spreads.
So the $100 wide spreads are definitely giving up some income in exchange for that less risky (to me) position. I think of the roll into 2x $50 wide spreads to be a mechanism to reclaim some of the premium missed out on by starting with the 2x $50s, while affording me the choice to do nothing if we're just too close ATM to take the risk.