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Since I started following you, I have been doing this actively with my portfolio. I screwed myself by selling a $140 call on Amazon around earnings and it jumped well over that so all the shares were sold. Since then I have learned about rolling options, if the price jumps to $150 and I had sold a call for say $140 on 6/22 I could roll out of it. Meaning I could buy to close the original call and then sell to open at a higher strike further in the future and probably earn more money or break even.

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It happens. I try to use covered calls to set a price I wouldn't mind selling at in a month. 10% jump in a month (10% out-the-money strike) + a few points in option premium makes me feel not terrible if it gets called away. Locked in a 12-15% monthly return.

Check this about some situations I'll roll an option:

https://effsigive.substack.com/p/option-basics-part-6-rolling-options

https://effsigive.substack.com/p/optimizing-your-investment-account-c0e

It isn't just for when your option is ITM. Sometimes extending a few days before expiration lets you re-up at nice premium too.

Also, when covered calls get assigned due to a big monthly move, and if I still like the stock, i'll use the cash for a cash secured put. So in your case, start selling $140 monthly puts on Amazon assuming the premium is decent. That way you get paid for the price to come back to you. (see couple part series here)

https://effsigive.substack.com/p/optimizing-your-investment-account

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