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I am curious as to if it would be better to pull the trigger early and sit on cash, or keep holdings and then average in, in the case of a big drop?
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It depends. If an investor is young, I would recommend to keep holding, and, as you say, average in, in case of a big drop.
Pull the trigger early and sit on cash? Well, cash is trash, as they say. If your crystal ball is 100%, maybe this will work. Mine is not 100%.
You could sell calls, I have done so, slightly. You could buy puts, but puts are a wasting asset, see above reference to percentage of crystal ball infallibility.
In normal times, you could buy a chunk of long term treasurys, but these are not normal times.
My plan? Keep some powder dry, but don't go crazy. If the markets crash, buy XIV.
I also have a small exposure to gold and bitcoin.