Common Tax Mistakes to Avoid When Filing as a Freelance

Navigating tax obligations can be challenging for freelancers. This comprehensive guide will cover common pitfalls in tax preparation and provide actionable advice to avoid them, ensuring you remain compliant and maximize your deductions.

Askia Roberts
May 15, 2024

1. Not Reporting All Income

  • Overview: Freelancers must report all income from services provided, regardless of whether they receive a 1099 form from their clients.
  • Tips: Maintain detailed records of every transaction. Utilize accounting software to track income accurately throughout the year.
  • Qualification: Ensure you understand the threshold for issuing 1099s and include all income, even if a client does not send a form.

2. Mixing Personal and Business Expenses

  • Overview: A common error for new freelancers is not separating business expenses from personal expenses, complicating deductions and potentially triggering audits.
  • Tips: Open a separate bank account and credit card for business transactions only. This separation simplifies record keeping and tax filing.
  • Qualification: Consult with a tax professional to clearly define which expenses can be considered business expenses.

3. Neglecting to Pay Estimated Taxes

  • Overview: Freelancers are required to pay estimated quarterly taxes if they expect to owe $1,000 or more when their return is filed.
  • Tips: Calculate your estimated taxes using last year's tax return as a baseline. Adjust quarterly payments based on fluctuating income to avoid underpayment penalties.
  • Qualification: Use IRS Form 1040-ES to figure and pay these taxes or consult with a tax advisor to assist in calculating the correct amounts.

4. Incorrectly Deducting Expenses

  • Overview: Deducting ineligible expenses can lead to penalties. Understanding what can be legally deducted is crucial.
  • Tips: Familiarize yourself with IRS guidelines on deductible business expenses. Keep receipts and detailed logs to justify deductions.
  • Qualification: Regularly review the IRS’s updates on deductible expenses and seek professional advice when unsure.

5. Failing to Claim Home Office Deductions

  • Overview: Many freelancers work from home but often miss out on claiming home office deductions due to confusion over eligibility.
  • Tips: Use the Simplified Option for home office deduction for a straightforward calculation ($5 per square foot of home used for business, up to 300 square feet).
  • Qualification: Ensure the space is regularly and exclusively used for business and meets the IRS criteria for a home office.

6. Not Keeping Adequate Records

  • Overview: Poor record-keeping can prevent you from claiming legitimate deductions and result in penalties during an audit.
  • Tips: Implement a systematic approach to record keeping. Digitalize receipts and track expenses and income using accounting software.
  • Qualification: Retain all tax records for at least three years from the date you file your income tax return.

7. Missing Deadlines

  • Overview: Late filing and payment can result in penalties and interest charges, increasing the overall tax burden.
  • Tips: Set reminders for tax deadlines using digital calendars. Consider hiring a tax professional to handle filings and deadlines.
  • Qualification: Stay informed of federal and state tax deadlines, which can vary.


Freelancers face unique tax challenges. Avoiding these common mistakes not only ensures compliance but can also optimize your tax situation. Implementing the recommended practices will provide peace of mind and potentially reduce your tax liabilities.

At RTW Advisors, we specialize in helping small business owners navigate complex tax regulations and optimize their tax strategies. If you have any questions or need assistance with your tax planning and preparation, please contact us.