This covered call trick mainly relies on theta decay. So, you don’t sell the calls one year out. You usually sell them under two months. For ex BRK.B 43 DTE 530 call is $2.50 (0.18 Delta). You can pick the strike depending on how aggressive you are. In a taxable account, you can be aggressive as you don’t have to worry about taxes.
You can let it expire if it is OTM or you can close it earlier for a pre-determined profit. Say you made 30% /50% much earlier (like a week). And you open another on the day when the stock goes up.
If it is ITM, you roll it. Of course, you lose it in the first transaction. But you are betting that the stock will not go crazy again. It is like losing the battle, but winning the war. Another way to recover is to sell only few options as an initial position and increase it when you roll. Say if you have 1000 BRK/B shares, you sell 3 options first and when you roll, you sell 6.
The underlying stock selection is very important. If you choose SPY or BRK/B most of the days they won’t move much, but the premiums will be lower. If you do it on a meme stock, the premiums will be higher.
All of the above options are when you don’t want to lose the underlying. But there are few reddit groups (thetagang/optionswheel) who sell CCs aggressively for more premium. When they get called they turn around and sell cash secured puts. Once assigned with the puts they sell covered calls again. They call it “The Wheel”.
But selling puts come with it’s own risks as the stock might crater and you are left holding the bag and can not sell CC above your assigned price. If you do, you will get low premium and give up the upside.
You sell CCs on the stocks you want to own (SPY/BRK) so that you will be in the market and have some upside and don’t mind if it goes down.
There are few ETFs like QYLD/JEPI who do covered calls.
That said, with all the above monkey business, in all of the back testing, buy and hold beats selling CCs long term. At best one can expect to make low single digits. It may be worthwhile for somebody with a large portfolio and some time on their hands.
It is similar to picking stocks to beat the index (buy low, sell high). Some people manage to pull it off. Otherwise we won’t be here discussing stocks. The same can be applied to selling CCs (Sell high, buy low).