Tax Season 2026: What Contractors, Freelancers & Gig Workers Must Do to File 2025 Taxes & Maximize Deductions

The 2026 tax filing season opened in late January, with most individual returns, including those with self-employment income, due by April 15, 2026. If you’re a contractor, freelancer, or gig worker, you’re responsible not only for income tax, but also self-employment tax, which covers Social Security and Medicare at a combined 15.3% on net earnings.

Here’s what you need to know this tax season and how to prepare with confidence.

Gather All Your 2025 Income Documents Early

Start by collecting these essential forms and records:

• Form 1099-NEC or 1099-MISC from clients who paid you $600+ (for non-employee compensation).
• Form 1099-K from payment platforms (e.g., PayPal, Stripe, or gig apps like Uber, DoorDash) if thresholds were met—note that reporting rules continue to apply even for smaller amounts.
• Records of any cash, check, or other payments not reported on forms (all gig income is taxable, even under $600).
• Bank statements, invoices, and payment app summaries.

Pro tip: Track everything year-round to avoid scrambling now.

Track and Maximize Your Business Deductions

As a self-employed individual, you report income and expenses on Schedule C (Profit or Loss from Business) with your Form 1040. Deducting legitimate business expenses lowers your taxable income and self-employment tax.

Common deductions for contractors, freelancers, and gig workers include:

• Home office (if you use a dedicated space)
• Mileage or vehicle expenses (track business miles carefully)
• Supplies, equipment, software, and professional fees
• Internet, phone, and utilities (business portion)
• Advertising, marketing, and travel
• Half of your self-employment tax
• Health insurance premiums (if self-paid)

Keep receipts, logs, and mileage records – digital apps make this easier. Accurate tracking can save you thousands.

Don’t Forget Quarterly Estimated Taxes

If you expect to owe $1,000+ in taxes for 2025 (common for self-employed), you should have made quarterly estimated payments. The final 2025 Q4 payment was due January 15, 2026.

For 2026 income, start planning now: Set aside 25-30% of earnings for taxes and make payments due April 15, June 15, September 15, and January 15 (next year).

Missing these can lead to penalties, use IRS Form 1040-ES or tax software to calculate.

Need Help Getting It Right?

At JIL & Associates, we help self-employed professionals stay compliant, maximize deductions, and reduce tax liability.

📞 Call (630) 828-3648 or visit jiladvisors.com and book a free consultation today.