Tax Season Preparation Checklist for Freelancers (2026)

Tax season doesn't have to mean panic. Freelancers who prepare systematically file faster, claim more deductions, and stress less.

This checklist breaks down everything you need to do—organized by timeframe—so you're ready when April arrives.

Key Dates for 2026 Tax Season

Phase 1: Gather Your Documents

Income Documents

• [ ] 1099-NEC forms from all clients who paid you $600+
• [ ] 1099-K forms from payment processors (PayPal, Stripe, Venmo, etc.)
• [ ] 1099-INT for bank interest earned
• [ ] 1099-DIV for dividend income
• [ ] 1099-B for investment sales
• [ ] W-2 if you had any W-2 employment
• [ ] Records of cash/check payments not reported on 1099s
• [ ] Income summary from your accounting system

Note: 1099s should arrive by January 31. Don't file until you have them all—or confirm clients aren't sending them.

Expense Documentation

• [ ] Bank statements for all business accounts (12 months)
• [ ] Credit card statements for business cards (12 months)
• [ ] Receipts for expenses $75 and over
• [ ] Mileage log with dates, destinations, and business purpose
• [ ] Home office measurements and utility bills
• [ ] Health insurance premium statements (Form 1095-A, B, or C)
• [ ] Retirement contribution records (SEP IRA, Solo 401k statements)

Personal Documents

• [ ] Previous year's tax return (for reference)
• [ ] Social Security numbers for you, spouse, dependents
• [ ] Bank account and routing numbers (for direct deposit/payment)
• [ ] ID for identity verification (if e-filing for first time)

Phase 2: Organize Expenses by Category

Match your expenses to Schedule C categories:

Advertising & Marketing

• [ ] Social media ads
• [ ] Website costs (hosting, domain, design)
• [ ] Business cards, brochures
• [ ] Email marketing services
• [ ] SEO and content services

Office Expenses

• [ ] Software subscriptions
• [ ] Office supplies
• [ ] Postage and shipping
• [ ] Printing costs
• [ ] Computer accessories

Professional Services

• [ ] Accounting/bookkeeping fees
• [ ] Legal fees
• [ ] Consulting fees
• [ ] Freelance help (contractors you hired)

Travel

• [ ] Airfare
• [ ] Hotels/lodging
• [ ] Ground transportation
• [ ] Parking and tolls
• [ ] 50% of meals during travel

Vehicle Expenses

• [ ] Total business miles driven
• [ ] Gas receipts (if using actual method)
• [ ] Maintenance/repairs (if using actual method)
• [ ] Insurance (if using actual method)
• [ ] Lease payments (if using actual method)

Home Office

• [ ] Square footage of office and total home
• [ ] Rent or mortgage interest
• [ ] Utilities (electric, gas, water)
• [ ] Home insurance
• [ ] Repairs and maintenance

Equipment & Depreciation

• [ ] Computer and electronics purchased
• [ ] Furniture purchased
• [ ] Equipment purchased
• [ ] Prior year depreciation schedules

Education & Training

• [ ] Online courses
• [ ] Conference registrations
• [ ] Professional certifications
• [ ] Business books and subscriptions

Insurance

• [ ] Health insurance premiums (self-employed deduction)
• [ ] Business liability insurance
• [ ] Professional liability/E&O insurance

Other Deductions

• [ ] Business phone line
• [ ] Business portion of cell phone
• [ ] Business portion of internet
• [ ] Bank fees and merchant processing fees
• [ ] Professional memberships and dues

Phase 3: Calculate Key Deductions

Home Office Deduction

Simplified Method:

• Office square footage: _____ (max 300)
• Deduction: _____ × $5 = $_____

Actual Method:

• Office %: _____ sq ft ÷ _____ total sq ft = _____%
• Annual home expenses × business % = $_____

Compare both. Use the higher amount.

Calculate automatically with AlphaTax →

Vehicle Deduction

Standard Mileage:

• Business miles: _____ × $0.70 = $_____

Actual Expenses:

• Total vehicle expenses: $_____
• Business mile %: _____ business ÷ _____ total = _____%
• Deduction: $_____ × _____% = $_____

Compare both. Use the higher amount.

Track and compare with AlphaTax →

Retirement Contributions

• [ ] Calculate maximum SEP IRA contribution (25% of net SE income)
• [ ] Calculate maximum Solo 401(k) contribution ($23,500 + 25% employer)
• [ ] Decide contribution amount based on cash flow
• [ ] Fund account by tax deadline (SEP) or already funded (Solo 401k)

Optimize contributions with AlphaTax →

Phase 4: Review for Missed Deductions

Go through this list. Check anything you might have missed:

• [ ] Business use of personal cell phone
• [ ] Business portion of internet
• [ ] Professional subscriptions (news, industry publications)
• [ ] Small software purchases
• [ ] Online tools and services
• [ ] Business meals and entertainment (50%)
• [ ] Parking for business meetings
• [ ] Professional development books
• [ ] Business gifts ($25 limit per recipient)
• [ ] State/local business licenses and permits
• [ ] Business insurance premiums
• [ ] Professional association dues
• [ ] Bank and credit card fees
• [ ] Bad debts (invoices you'll never collect)

Phase 5: File or Extend

If Filing by April 15

• [ ] Complete Schedule C (sole proprietor) or appropriate business return
• [ ] Complete Schedule SE (self-employment tax)
• [ ] Complete Form 1040 with all schedules
• [ ] Review for errors before submission
• [ ] E-file or mail return
• [ ] Pay any balance due

If Requesting Extension

• [ ] File Form 4868 by April 15 (automatic 6-month extension)
• [ ] Pay estimated tax due with extension (extension is for filing, not paying)
• [ ] Calendar October 15 deadline

Remember: Extension to file ≠ extension to pay. Interest and penalties accrue on unpaid tax.

Phase 6: Plan for Next Year

After filing, set yourself up for an easier next year:

• [ ] Review what took longest—improve that process
• [ ] Set up better expense tracking system
• [ ] Schedule quarterly estimated payments in calendar
• [ ] Calculate and adjust quarterly payment amounts
• [ ] Open dedicated business bank account (if you haven't)
• [ ] Consider year-round tax planning with AlphaTax

Frequently Asked Questions

What if I'm missing a 1099?

Contact the client/company directly. If you can't obtain it, you're still required to report the income. Use your own records to determine the amount.

Should I wait for all 1099s before filing?

Yes, generally. Filing early and then receiving a 1099 you didn't include requires an amended return. Wait until mid-February when most 1099s have arrived.

Can I still contribute to retirement accounts?

SEP IRA: Yes, until tax filing deadline (including extensions).

Solo 401(k): Only if plan was established by December 31 of the tax year.

Traditional/Roth IRA: Yes, until April 15 (no extension).

What if I can't pay what I owe?

File anyway (even if you can't pay) to avoid failure-to-file penalties. Then set up an IRS payment plan. Failure-to-file penalty is much higher than failure-to-pay.

Stay Organized Year-Round

The best tax season prep happens throughout the year. AlphaTax helps you track expenses, estimate quarterly payments, and stay organized so tax season is just a review, not a scramble.

Start Organizing Your Taxes →