Year-End Tax Checklist for Independent Contractors: Get Ahead for a Stress-Free Tax Season

As the year draws to a close, independent contractors and self-employed individuals like yourself are gearing up for the upcoming tax season. Proper preparation now can save you time, money, and stress in the months ahead. Let me guide you through a comprehensive year-end tax checklist to ensure you're well-prepared for the next tax season.

  1. Review Your Income and Expenses:

    • Take stock of your earnings and expenses throughout the year. Ensure that all income is accurately recorded, and don't forget to account for any deductions or business-related expenses. This is the foundation for accurate tax filings.

  2. Maximize Deductions:

    • Identify potential deductions specific to your industry. Common deductions for independent contractors include home office expenses, mileage, professional development, and equipment purchases. By maximizing your deductions, you can reduce your taxable income.

  3. Organize Receipts and Documentation:

    • Create a system to organize receipts and other important documents. Proper documentation is crucial for substantiating expenses and justifying deductions in case of an audit. Consider using digital tools for easy record-keeping.

  4. Retirement Contributions:

    • Explore opportunities to contribute to retirement accounts before the year-end. Not only will this help secure your financial future, but it may also provide additional tax benefits. Consult with a financial advisor to determine the best strategy for your situation.

  5. Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs):

    • If you have an HSA or FSA, review your contributions and make any necessary adjustments before the end of the year. Utilizing these accounts can provide tax advantages for eligible medical expenses. Also remember that FSA accounts are generally “use it or lose it” — meaning that these balances will not roll forward into the next year. After doublechecking the specifics of your account, consider eligible expenses that you might pay (or prepay) before the end of the year.

  6. Estimated Tax Payments:

    • Ensure that you've made all required estimated tax payments throughout the year. Underpayment may result in penalties, so double-check your payments to avoid surprises come tax time.

  7. Charitable Contributions:

    • If you've made charitable donations, gather documentation to support these contributions. Charitable deductions can be a valuable way to give back while reducing your tax liability, assuming you choose to itemize your deductions.

  8. Plan for the Future:

    • Reflect on your business goals and financial objectives for the upcoming year. Discuss your plans with your CPA to ensure you're well-prepared for any changes that may affect your tax strategy.

By proactively addressing these key areas before the year-end, you'll set the stage for a smooth and stress-free tax season. Of course, I am here to support you every step of the way. If you have any questions or need personalized advice, don't hesitate to reach out. Together, we'll navigate the complexities of tax season and set the course for your financial success in the coming year.


Any and all information included in this webinar and presentation is provided for informational purposes only and is not to be relied upon as a professional opinion. All content does not constitute professional advice and is not guaranteed to be complete, accurate, reliable, current, or error-free. By consuming this content, you accept and agree that following any information or recommendations provided therein and all channels of digital content is at your own risk.

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Common Tax Questions from 1099 Independent Contractors and Self-Employed Individuals (And Their Answers)