1099 Worker Tax Season Checklist

Clients paying you $600+ must send this. Demand it by Feb 1 if not received.

PayPal, Stripe, Venmo, eBay, Etsy, etc. Threshold: $5,000 for 2024, $600 for 2025.

Applies if you received rents, royalties, or certain other income.

Cross-check against 1099s received — platforms sometimes under-report.

All accounts that received business income. Reconcile against invoices.

Export full year CSV from Stripe, PayPal, etc. for reconciliation.

Regular and exclusive use required. Simplified method: $5/sq ft up to 300 sq ft.

2024 standard rate: 67¢/mile. Must have date, destination, business purpose.

May qualify for Section 179 immediate expensing or bonus depreciation.

Adobe, Figma, Notion, Slack, GitHub, etc. — all deductible if for business.

Deduct the business-use percentage (typically 50–80%).

Above-the-line deduction — reduces AGI, not just Schedule C.

Contributions must be made by tax deadline (+ extensions) to count for 2024.

Courses, books, conferences directly related to your current business.

Must document: date, business purpose, attendees. 50% deductible in 2024.

Flights, hotels, transportation. Must be primarily for business.

IRS Form 1040-ES. Check IRS Online Account or bank records.

IRS Form 1040-ES.

IRS Form 1040-ES.

IRS Form 1040-ES.

Most states require quarterly payments if you expect to owe $500+.

Needed for AGI to e-file. Your CPA or tax software will need last year's numbers.

If you have an LLC or formal entity, get your EIN from IRS.gov if needed.

Net operating losses or capital loss carryforwards from prior years.

If you have depreciating assets, your CPA needs the existing depreciation schedule.

One per business activity. Lists gross income, all deductions, net profit/loss.

Calculates the 15.3% SE tax on your Schedule C net profit.

Only if using the actual-expense method for home office (not simplified).

Required if you have depreciating business assets or Section 179 deduction.

20% pass-through deduction for sole props and LLCs. Confirm your CPA applies it.

You need W-9s to issue 1099-NECs to any vendor/contractor you paid $600+.

Due to contractors Jan 31; to IRS Feb 28 (paper) / Mar 31 (e-file).

Name, address, SSN/EIN, total paid. Required if you paid anyone to do work.