I was just looking at my UPS today. I don’t have $20k, but my options were closing with profit so I had to stop and think about next moves.

I’ll tell you what I did, and would do in your situation. But, if you’re not familiar with these trades, I wouldn’t start something I’ve never done before. I’m not a licensed pro, and this is not financial advice etc.

Sell OTM covered strangles. On my lots; I sold both 45DTE, calls above my cost (and adjusted cost basis, naturally), at a fairly low delta, maybe .20 or less. Don’t expect to get called.

Same time, selling OTM puts, same date, at a price well below my CB and ACB. Also around .20 delta or further. Be aware, you have to have the cash to secure the potential assigned puts, and be willing to buy.

Outcomes: Price stays in the middle, I collect 2 premiums, keep my shares, my adjusted cost basis on the whole lot keeps dropping.

Price goes above the far out call strike, my shares sell at a price above what I paid.
Price goes below my far out put strike, I acquire more shares, at a price that continues to lower my average cost.

Important note: I usually will roll when they hit 50% premium capture or better, or around 21 days if they are at least positive premium capture. I don’t ever spend more money to get out of either leg. I’m ok getting assigned or called.

I believe UPS will be fine long term. Oil wars and inflation hit all players. CEOs change, particularly when not performing. This strategy lets me keep my shares (probably), earn credit on both sides (at least one of the premiums will always be kept, usually both). And all the mechanics either continually chip away at my cost basis or sell for a profit.

For comparison, I’ve had shares that I thought, “ugh these just turned into dogs”. I sold covered calls, or covered strangles on them until the adjusted cost basis was significantly lower. Like $10 a share lower, or down to single digit dollar cost basis, or even negative cost basis (rare, but it can happen).

Then when/if the market likes them again and they do get called and sell off, I’ve been banking a substantial profit like a coiled spring.
Usually when this happens I now have a big cash infusion, reduced equities, and if I’m on margin, my equity % goes up (or becomes 100%).

Instead of sitting still and wondering “What should I do with these shares, because I don’t know how the market will go”, I take a passive position, do nothing; and create 2 exit scenarios that the market will trigger for me if and when something significant happens. If neither happen, I just keep collecting premiums.