Question

I just started doing DoorDash in August of 2021 and I failed to track details of my expenses (e.g. mileage). Given this, should I skip the upgrade to Self-Employed?

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You have to report all income. All you can do is make reasonable estimates.

If you are not entering expenses, you don't need the Self-Employed version. However, you should be able to determine some expenses. See:

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