Comprehensive Annual Tax Calendar for Individuals and Small Business Owners

Navigating tax deadlines can be overwhelming for individuals and small business owners alike. Missing a filing or payment due date can lead to costly penalties, interest, or IRS scrutiny. To help you stay organized and compliant, we have created this annual tax calendar, designed to be a timeless resource for managing federal tax obligations. Whether you’re an individual taxpayer, a freelancer, or a small business owner (e.g., sole proprietor, LLC, S-Corp, or partnership), this calendar outlines key tax deadlines, estimated payment schedules, and planning tips to keep your taxes on track year-round.

This guide is tailored to be user-friendly for “normal people” while addressing the specific needs of small business owners. It includes federal income tax deadlines, payroll tax requirements, and strategic planning reminders, with explanations to ensure clarity. Partner with our Enrolled Agent-led tax advisory firm to simplify your tax responsibilities and avoid surprises.

Write to Tax@S-CorpTax.com, or call (858) 779-4125.

A tax calendar helps you:

• Stay Compliant: Meet IRS and state filing and payment deadlines to avoid penalties.

• Plan Ahead: Budget for estimated tax payments and major tax events.

• Maximize Deductions: Time expenses and contributions to optimize your tax return.

• Reduce Stress: Stay organized with a clear schedule of tax obligations.

This evergreen calendar focuses on recurring federal tax deadlines that apply annually, with notes on state variations and planning tips. Always check with your tax advisor or the IRS for updates to tax laws, inflation-adjusted deadlines, or state-specific requirements.

Key Deadlines and Planning Tips

January

Deadlines for Individuals:

• January 15: Fourth-quarter estimated tax payment for the prior tax year (if you’re self-employed, have side income, or don’t have enough tax withheld). Covers income from October 1 to December 31 of the prior year.

• January 31: Employers issue Form W-2 (wages) to employees and Form 1099-NEC (nonemployee compensation) to freelancers/contractors for the prior year. Individuals receive these forms to prepare their tax returns.

Deadlines for Small Business Owners:

• January 31:

• File Form W-2 with the Social Security Administration (SSA) and provide copies to employees.

• File Form 1099-NEC with the IRS and provide copies to contractors paid $600 or more in the prior year.

• File Form 940 (Federal Unemployment Tax Act, FUTA) for the prior year, reporting unemployment taxes (if not deposited earlier).

• File Form 941 (Employer’s Quarterly Federal Tax Return) for the fourth quarter of the prior year (October–December), reporting withheld income taxes and FICA (Social Security/Medicare).

Planning Tips:

• Individuals: Gather W-2s, 1099s, and receipts for deductible expenses (e.g., charitable donations, medical costs) to prepare for tax filing. Review your prior year’s return to identify missed deductions.

• Small Business Owners: Ensure your payroll system is set up to issue W-2s and 1099s accurately. Reconcile fourth-quarter payroll taxes and confirm FUTA deposits. Schedule a consultation with an Enrolled Agent to review your business tax strategy for the new year.

• Both: If you expect a refund, file early to receive it sooner. Consider increasing withholdings or estimated payments if you owed taxes last year.

February

Deadlines:

• No major federal tax deadlines for individuals or small businesses, unless you missed January 31 filings (late filings incur penalties).

Planning Tips:

• Individuals: Continue organizing tax documents, including mortgage interest (Form 1098), student loan interest, and education expenses (Form 1098-T). Explore tax-advantaged accounts like IRAs for contributions deductible on your upcoming return.

• Small Business Owners: Review your accounting records for accuracy before tax season peaks. If you operate an LLC or S-Corp, confirm your books align with Schedule K-1 reporting needs.

• Both: Meet with an Enrolled Agent to discuss tax-saving opportunities, such as maximizing deductions or adjusting estimated payments for the current year.

March

Deadlines for Small Business Owners:

• March 15:

• File Form 1120S (S-Corp income tax return) or Form 1065 (partnership/LLC return) for the prior year, including Schedule K-1s for owners. Request an extension (Form 7004) if needed, but taxes owed are due by this date.

• Pay corporate taxes for S-Corps if not filing an extension.

Planning Tips:

• Individuals: Finalize your tax preparation to file by April 15. If self-employed, review business expenses (e.g., home office, mileage) to claim on Schedule C.

• Small Business Owners: Ensure your accountant has all financial records for S-Corp or LLC filings. If extending your return, estimate taxes owed to avoid underpayment penalties. Review payroll compliance for the first quarter.

• Both: Consider contributing to a traditional IRA by the tax filing deadline (typically April 15) to reduce taxable income for the prior year.

April

Deadlines for Individuals:

• April 15:

• File Form 1040 (individual income tax return) for the prior year or request an extension (Form 4868). Taxes owed are due even if you extend.

• First-quarter estimated tax payment for the current year (covers January 1–March 31 income).

• Make IRA contributions for the prior tax year (traditional or Roth, subject to income limits).

Deadlines for Small Business Owners:

• April 15:

• File Form 1040 for sole proprietors (Schedule C) or single-member LLCs, reporting business income. Request an extension if needed, but pay taxes owed.

• File Form 941 for the first quarter of the current year (January–March).

• Pay first-quarter estimated taxes for self-employed owners or pass-through entities (S-Corps, LLCs).

Planning Tips:

• Individuals: File early to avoid last-minute stress. If extending, estimate taxes accurately to avoid penalties. Review eligibility for credits like the Earned Income Tax Credit (EITC) or Child Tax Credit.

• Small Business Owners: Reconcile first-quarter payroll and sales tax records. If you extended your S-Corp or LLC return, finalize financials for the September/October deadlines. Assess your business structure (e.g., LLC vs. S-Corp) for tax efficiency.

• Both: Work with an Enrolled Agent to identify last-minute deductions or credits. Budget for estimated tax payments to avoid cash flow issues.

May

Deadlines:

• No major federal tax deadlines, unless you missed April filings.

Planning Tips:

• Individuals: If you received a refund, consider adjusting withholdings to increase take-home pay. If you owed taxes, increase estimated payments or withholdings for the current year.

• Small Business Owners: Review second-quarter financials and payroll compliance. If you’re behind on payroll taxes, contact an Enrolled Agent to negotiate with the IRS and avoid penalties.

• Both: Mid-year is a great time to assess your tax strategy. Schedule a consultation to explore deductions, retirement contributions, or business expense planning.

June

Deadlines for Individuals:

• June 15: Second-quarter estimated tax payment for the current year (covers April 1–May 31 income).

Deadlines for Small Business Owners:

• June 15: Second-quarter estimated tax payment for self-employed owners or pass-through entities.

Planning Tips:

• Individuals: Review your year-to-date income, especially if you have variable sources (e.g., freelance work). Adjust estimated payments to reflect changes in income or expenses.

• Small Business Owners: Evaluate your business’s profitability and cash flow. Consider prepaying deductible expenses (e.g., subscriptions, equipment) to reduce taxable income later in the year.

• Both: Explore tax-advantaged accounts like Health Savings Accounts (HSAs) or 529 plans for education savings.

July

Deadlines for Small Business Owners:

• July 31: File Form 941 for the second quarter of the current year (April–June).

Planning Tips:

• Individuals: If you extended your Form 1040, finalize your tax return for the October deadline. Gather any missing documents or receipts.

• Small Business Owners: Reconcile second-quarter payroll taxes and confirm timely deposits. Review your accounting software for accuracy before the third quarter.

• Both: Meet with an Enrolled Agent for a mid-year tax review to project your tax liability and identify savings opportunities.

August

Deadlines:

• No major federal tax deadlines.

Planning Tips:

• Individuals: Assess your withholdings or estimated payments to avoid underpayment penalties. Consider charitable contributions or medical expenses to itemize deductions.

• Small Business Owners: Review your business expenses for potential deductions (e.g., marketing, travel). If you’re planning major purchases (e.g., equipment), time them for depreciation benefits.

• Both: Start preparing for third-quarter obligations and year-end tax planning.

September

Deadlines for Individuals:

• September 15: Third-quarter estimated tax payment for the current year (covers June 1–August 31 income).

Deadlines for Small Business Owners:

• September 15:

• Third-quarter estimated tax payment for self-employed owners or pass-through entities.

• Extended Form 1120S or Form 1065 (S-Corp or LLC/partnership returns) due for the prior year.

Planning Tips:

• Individuals: If you’re self-employed, track business expenses diligently to maximize Schedule C deductions. Review retirement contributions to 401(k) or IRA plans.

• Small Business Owners: Finalize extended S-Corp or LLC returns to avoid late penalties. Prepare for fourth-quarter payroll and sales tax filings.

• Both: Consult an Enrolled Agent to optimize year-end tax strategies, such as bunching deductions or deferring income.

October

Deadlines for Individuals:

• October 15: Extended Form 1040 due for the prior year (if you filed Form 4868).

Deadlines for Small Business Owners:

• October 15: Extended Form 1040 due for sole proprietors or single-member LLCs.

• October 31: File Form 941 for the third quarter of the current year (July–September).

Planning Tips:

• Individuals: If you extended your return, ensure all documents are submitted to avoid late penalties. Review your tax liability to plan for the next year.

• Small Business Owners: Reconcile third-quarter payroll and confirm timely tax deposits. Begin year-end tax planning, including equipment purchases or bonuses for depreciation deductions.

• Both: Meet with an Enrolled Agent to finalize extended returns and project fourth-quarter estimated taxes.

November

Deadlines:

• No major federal tax deadlines.

Planning Tips:

• Individuals: Make charitable contributions or pay property taxes by December 31 to claim deductions on your upcoming return. Maximize HSA or 401(k) contributions.

• Small Business Owners: Review your profit-and-loss statement to estimate year-end taxes. Consider prepaying expenses or deferring income to lower taxable income.

• Both: Schedule a year-end tax planning session to identify last-minute savings opportunities.

December

Deadlines:

• No major federal tax deadlines until January.

Planning Tips:

• Individuals: Finalize deductible expenses (e.g., donations, medical costs) and retirement contributions for the current tax year. Adjust withholdings if you expect a large refund or owe taxes.

• Small Business Owners: Issue employee bonuses or purchase equipment by December 31 for depreciation deductions. Reconcile fourth-quarter financials for January filings.

• Both: Work with an Enrolled Agent to execute year-end strategies, such as bunching deductions or timing income to stay in a lower tax bracket.

Additional Notes and Considerations

State Tax Deadlines

While this calendar focuses on federal taxes, state tax deadlines vary. For example:

• California: Franchise Tax Board filings for LLCs are due April 15, with estimated tax payments aligning with federal dates.

• New York: Corporate and personal income tax deadlines often mirror federal dates, but sales tax filings may have different schedules.

• Action: Check your state’s revenue department website or consult an Enrolled Agent for state-specific deadlines.

Extensions and Penalties

• Extensions: Filing extensions (e.g., Form 4868 for individuals, Form 7004 for businesses) extend the filing deadline but not the payment deadline. Pay estimated taxes owed by the original due date to avoid penalties.

• Penalties: Late filing penalties are 5% per month (up to 25%) of unpaid taxes, while late payment penalties are 0.5% per month. Interest accrues on unpaid balances.

Planning for Variable Income

• Individuals: If you have side gigs or freelance income, use the IRS’s Tax Withholding Estimator to calculate estimated payments.

• Small Business Owners: Monitor cash flow to cover quarterly estimated taxes and payroll obligations. Use accounting software to track income and expenses.

Working with an Enrolled Agent

Our Enrolled Agents can:

• Create a personalized tax calendar tailored to your income sources and business structure.

• File returns, make payments, and manage extensions on your behalf.

• Provide year-round tax planning to minimize liabilities and maximize deductions.

• Represent you before the IRS if you face audits or notices.

Why Choose SCORPIO TAX MANAGEMENT for Tax Compliance?

Staying on top of tax deadlines is easier with a trusted partner.

• Enrolled Agent Expertise: Our EAs are federally licensed and trained in tax law, ensuring accurate and compliant filings.

• Tailored Support: We customize strategies for individuals and small businesses, from sole proprietors to S-Corps.

• Proactive Planning: We help you anticipate tax obligations and optimize deductions year-round.

• Nationwide Representation: Our EAs serve clients in all 50 states, providing seamless support.

Conclusion: Stay Ahead with Our Evergreen Tax Calendar

This comprehensive tax calendar is your roadmap to staying organized, compliant, and financially savvy. By tracking key deadlines and planning strategically, you can avoid penalties, reduce your tax burden, and focus on what matters—whether it’s your personal finances or growing your small business. Our Enrolled Agents are here to simplify your tax journey, offering expert guidance every step of the way.

Ready to take control of your taxes? Contact us today for a consultation, and let us help you stay on track with a personalized tax strategy. Download this calendar as a reference, and partner with us to make tax season stress-free!