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My cost base of Nvidia is $1 so for me to lose is that Nvidia gets back to way before COVID valuation.

Nvidia is more worth than $1 per share on gaming alone.

Totally fair. If you've got a great cost basis, you can stress less. The question then becomes what feels worse:

Watching a position you sold double or watching a position you're holding get cut in half?

There is one answer to this question which is called options. Selling short term OTM CCs with half of premium being used to buy ITM Calls (1/3 protection of the CC), OTM Calls (protection against gap up) and longterm OTM Puts (earn money when Nvidia nose dives).

There is no free money from option selling, you are taking some form of directional risk whether you realise it or not

This looks like the house money effect. It's sort of a corollary to the sunk cost fallacy.

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