I bought VTSAX in 2020 at $56.00, 25k shares. Thinking of selling before it goes lower than that

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Why? So you can you buy them back when they're more expensive?

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I missed the part where this sale they’re discussing would be a gain, sorry for the confusion.

So you have $2.25M with $825k in gains. If you sell you will owe a lot of tax. I’m in a similar situation. I bought SPY put options and sold out of the money call options. I’ve held my losses to about 5%. The puts can provide 1:1 gains for each dollar lost in VTSAX for a lot less than the taxes on your gains. Depending on how far out of the money you go with the put and calls you can still have some up side benefit and/or downside exposure.

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Awesome

Why would you sell? Just hold. That’s 1.4m

Just buy more when it dips.

Time in market > timing the market

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