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I agree this is a shitty edge case but when switching from W2 to a 1099 is really just a semantic difference then switching from W2 to unemployed in the first few months.

BTW I'm pretty sure there's a way around this if he incorporated and made himself a W2 employee and paid himself a set salary but I'm not an expert.

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Switching from W2 to 1099 is by no means a semantic difference. If it is, then it's probably illegal to be treated as an independent contractor.

I think he meant there's no difference between being unemployed and just starting as 1099, since there's basically no taxes paid to show you're making any income for a while.

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