Concrete example: you have 2000 $TSLA shares, you sell 20x Jan 2021 $1675 strikes ~92 per contract = $184k - actually I wouldn't sell these now, as premiums just took a bit of a hit, you'd time it when it's on the up, like this last Tuesday, pricing was closer to $100, so $200k to last you 12 months (enough, too much, I don't know your situation, but it's about the number I'd be looking for)
Possible outcomes:
- your shares get called away before the strike date and you receive $3.35M cash
- the SP drops, IV crushes, the premiums on these calls goes so low, you decided to rebuy them, you keep the delta with the initial premium (note that the drop accelerates towards the expiry date due to time-decay)
- you hold to expiry: a) the SP is below the strike price - you keep the cash or b) the SP is above the strike price, your shares are gone, you get $3.35M cash
It basically hinges on whether you think the SP would double over the next year and whether you'd be happy to let your shares go at that price.
If they did get called away, and you receive all that cash, then you can immediately sell cash-covered puts for more income. In the case of puts, I would sell them shorter time-frame as you can be more aggressive with the pricing, working on the basis that you want to get those shares back.
Where it gets complicated is whether you have taxes due on the realised gains in the situation where your shares get called away. In my case not, so this type of trading is a no-brainer.