Well, I bought and HODL'd my main account for the best part of five years, from Feb 2016, but the need to get some cash out over the next 12 months changed the dynamic, so I started trading against the shares to see if I could get the $1M I need without selling any shares. It's a long and complicated, but a good example is that when I started selling calls against my 2900 shares I had added 350, by March - then when we started to drop I allowed 1400 on 4/40 to exercise @$702.50 so I had my cash already that I needed, I re-bought enough shares at $640 to bring me back to 2000 and have been selling puts against the cash since then - May was a bit brutal as I was chasing puts down, but now I'm making all that back on the way up
More interesting is my other account where I had $3500 in September 2019, and without any further capital injection is was $1.8M at the ATH in January - that was with $200k cash taken out for my house purchase
You have to note that I'm playing it aggressively, I sell ITM/ATM calls as they bring the best premiums, but if the SP moves dramatically (as it did in May, as it has done this week), it can be a headache. Playing on both directions (selling puts and calls) means you hedge your bets and after May I've learned not to over-commit myself and now all my positions are fully covered, so I can roll them as I wish without worrying about cash-reserve (I don't have a margin account)
Example, sold ont he last two days, 22x 7/2 ccp695, raking in around $66k, will they expire worthless? Will the be ITM, ATM, OTM, DOTM?? I don't really care, because I'll roll them a week later a the same strike is typically +$9 per contract, that's another $20k cash, only risk is early exercise, but that's very rare and if it happens, so what...
You can also play it very safe. Selling weeklies 15% about the SP on a Tuesday will usually net you $0.50-$1 in premium, it's very rare the times they'll go ITM, if they do you roll them out and up
** I call these "monthlies"
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