Freelancer Tax Prep Checklist Prompt

Act as an expert US tax strategist and freelance business consultant with 12+ years helping independent contractors maximize legitimate deductions while staying compliant. Analyze the situation and produce a personalized tax preparation checklist with documents, deadlines, and simple action steps. Use USD and US federal timelines; note that state rules vary.

Inputs

• Profession/industry: {profession}

• Primary income streams: {income_streams}

• Current expense tracking method: {tracking}

• Work location setup: {location_setup}

• Estimated annual freelance income: {income_est}

Output format (return this only)
A) Heading: Profile Snapshot (Plain English)

• One paragraph summarizing the freelance setup, income complexity, and tracking method, plus any likely deduction hotspots for this profile.

B) Heading: Income Documentation (Collect These)

• 1099‑NEC/1099‑K from each client/platform; missing forms → use invoices and bank statements.

• Year‑end payout summaries from platforms (download PDFs).

• Invoices issued, payment receipts, and W‑9 copies sent to clients.

• Interest income 1099‑INT, dividend 1099‑DIV (if business accounts earn interest).

• Notes for mixed business/personal accounts: mark business deposits/highlight transfers.

C) Heading: Categorized Business Expenses (Track and Tag)

• Software and subscriptions (design tools, cloud storage, domains, email).

• Equipment and peripherals (laptop, monitor, phone, accessories).

• Office supplies and postage.

• Advertising and marketing (ads, portfolio hosting, printing).

• Professional services (bookkeeper, CPA, legal).

• Education and training (courses, certifications, conferences).

• Bank/processing fees (PayPal, Stripe, marketplace cuts).

• Meals with clients (50% deductible; note who/what/when).

• Dues and memberships (professional associations).

• Insurance (professional liability, business rider).

• State/local business licenses and fees.

D) Heading: Home Office Deduction (Pick a Method)

• Simplified method: $5 per square foot up to 300 sq ft (no receipts required).

• Actual expense method: business‑use % of rent/mortgage interest, utilities, internet, renters/home insurance, property tax, depreciation if owned.

• Requirements: space is regular and exclusive for business; keep photos/floor plan and utility statements.

• Action: calculate square footage and choose method with higher benefit; keep a worksheet.

E) Heading: Vehicle and Travel

• Mileage log: date, start/end location, business purpose, starting/ending odometer; keep with fuel and maintenance receipts.

• Methods: standard mileage rate (preferred for simplicity) or actual expenses (fuel, insurance, maintenance, depreciation) times business‑use %.

• Parking and tolls are separate and fully deductible.

• Travel: airfare, lodging, rideshare, per‑diem meals (50%); keep itinerary and agenda to prove business purpose.

F) Heading: Equipment and Supplies (Capital vs. Current)

• Section 179/bonus depreciation for qualifying equipment placed in service this year (consult limits).

• De minimis safe harbor: expense items ≤ $2,500 per invoice/item.

• Keep purchase receipts, serial numbers, and “in service” dates.

G) Heading: Professional Development

• Courses, certifications, webinars related to current business (not new trade).

• Books and research materials.

• Event tickets and travel (business purpose documented).

H) Heading: Quarterly Estimated Taxes (Federal)

• Deadlines (typical): Apr 15, Jun 15, Sep 15, Jan 15 (following year).

• Calculate using safe harbor: 100% of last year’s total tax (110% if prior AGI > $150k) split by four, or use current‑year projection.

• Action: set calendar reminders one week prior; pay via EFTPS or IRS Direct Pay; save confirmations.

• Consider separate savings account: move 25–30% of each payment received for taxes (adjust for state).

I) Heading: Annual Filing and Extensions

• Annual return due: Apr 15 (or next business day); extension Form 4868 extends filing to Oct 15 but not payment—pay estimate with extension.

• Form checklist: Schedule C (business), Schedule SE (self‑employment tax), Form 8829 (home office actuals), depreciation forms if applicable.

• State filings and city taxes: note residency rules and local deadlines.

J) Heading: Record‑Keeping and Receipt Organization

• One inbox: email receipts → auto‑forward to an “Expenses” mailbox and cloud folder.

• Monthly routine: categorize transactions; attach PDFs/photos to each entry; reconcile to bank statements.

• Keep records for at least 3 years (7 if claiming bad‑debt or large loss).

• Backup: export a yearly archive (CSV + PDFs) to external storage.

K) Heading: Often‑Overlooked Deductions (Review)

• Phone/internet business‑use %.

• Portion of SaaS that’s billed annually (amortize monthly in books).

• Bank/credit card annual fees (business accounts).

• Client gifts (limit applies), postage/shipping for deliverables.

• Accessibility tools, transcription, captioning for client deliverables.

• Sales tax paid on business purchases (jurisdiction dependent).

L) Heading: Action Plan (This Month)

• Gather missing 1099s; request client statements for any gaps.

• Choose home office method and compute square footage or % use.

• Start/refresh mileage log; snapshot current odometer.

• Set quarterly tax reminders and open a dedicated “tax sweep” savings sub‑account.

• Tag and attach last 90 days of receipts in the tracking app.

M) Heading: Extension and “What If” Scenarios

• If behind on bookkeeping, file extension (Form 4868) by Apr 15 and pay a good‑faith estimate.

• If cash is tight, set up an IRS payment plan; avoid missing estimated deadlines going forward.

• If mixed personal/business accounts, separate now; use a business checking card for clean records.

Rules

• Keep language simple and actionable; use bullets only.

• Assume US federal rules; state/local items may differ—add state notes if specified.

• If an input is blank, proceed with reasonable freelancer defaults and note assumptions in Profile Snapshot.

• Avoid legal advice; provide educational guidance and checklists only.