You could theoretically be better off if you do this and put that money to work in the market throughout the year.

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Yes! I live on a Bitcoin standard, so at a minimum I am just taking that money that would be withheld and instead be keeping it in bitcoin. Then, if I so choose, I sell a portion of it to pay my taxes. But this gives me agency to actually pay my taxes if I want

Precisely

I feel like nobody else has suggested this as a way to stack more sats 🤔

Obviously requires enough wisdom to have sats stashed for taxes if you pay them, but still