Tax Readiness

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Plain-English guides for freelancers, gig workers and other simple Schedule C filers. Educational only — not tax advice.

Year-round

How much to set aside for taxes on 1099 income

No employer withholds for freelancers. Here's how to think about setting money aside as you earn — with a rough estimator.

Q1 peak

Are your records ready for Schedule C? A checklist

The income, expense and continuity records that make Schedule C filing smooth — and what to rebuild if they're missing.

Sep 15

Quarterly estimated taxes: deadlines and penalties

What estimated payments are, the four annual deadlines, and the records to keep so they reconcile.

Year-round

Standard mileage vs actual expenses for drivers

Two ways to deduct business driving, the records each needs, and why actual expenses usually means talking to a pro.

Jan–Feb

1099-K vs 1099-NEC — and what if there's no form

How platform and contract income forms differ, and why you report income even when no form arrives.

Year-round

Home office: who actually qualifies (and why not everyone)

The exclusive-use standard and why home office questions are worth a CPA/EA conversation.

Dec–Apr

What to prepare before you file

A short readiness pass to do before opening any tax software or meeting a preparer.

Year-round

A letter from the IRS or your state: what it means

Why notices have deadlines and why they're a reason to involve a CPA/EA before filing.

Year-round

Expenses freelancers forget to deduct

Ordinary-and-necessary business costs that are easy to overlook when records are messy.

Oct 15

Extended to October 15? Your plan

An extension moves the filing deadline, not the payment deadline — here's how to use the time.

Not sure where you stand?

Run the free 2–4 minute readiness check — no SSN, tax forms or bank data — and see exactly which records you're missing.

Check your tax-readiness