Your Annual Tax Calendar: A Monthly Guide to Stay Ahead

Taxes aren’t something to think about once a year. The most effective tax strategies are built gradually—month by month—by staying organized, anticipating deadlines and planning ahead rather than reacting under pressure. An annual tax calendar helps turn compliance into strategy and prevents missed opportunities that can quietly add up.

Below is a practical, high-level guide to what matters throughout the year.

January–June:
Laying the Foundation and Avoiding Early Mistakes

The first half of the year sets the tone for everything that follows. It’s a time to close out the prior year cleanly while positioning yourself for smarter decisions ahead.

• January: Gather tax documents, issue required 1099s, and confirm that business records and receipts from the prior year are complete and accessible.
• February: Review preliminary insight into your prior-year tax picture and flag issues that may require extension planning or estimated payment adjustments.
• March: Partnerships and S corporations approach filing deadlines. This is also a good time to reassess cash flow and confirm that withholding or estimated payments are on track.
• April: Individual tax returns and first-quarter estimated payments are due. If extending, ensure payments reflect realistic projections rather than rough guesses.
• May: With filing season behind you, revisit tax planning opportunities uncovered during preparation. Cleanup now avoids compounding problems later.
• June: Midyear is ideal for reviewing income, deductions and retirement contributions while there’s still time to adjust course.

July–December:
Turning Information Into Strategy

The second half of the year is where proactive planning has the greatest impact. This is when decisions can meaningfully shape your final tax outcome.

• July–August: Revisit cash flow, business performance and investment income to identify whether year-end planning is needed.
• September: Third-quarter estimated payments are due, making this a critical checkpoint for income accuracy and tax exposure.
• October: Extended returns are filed. Charitable planning, donor-advised funds and Roth strategies should move from ideas to action.
• November: Year-end tax planning accelerates. This is the window for income timing, deductions and retirement funding decisions.
• December: Finalize all actions before December 31. Missed deadlines here can’t be recovered.

A Calendar That Creates Confidence

An annual tax calendar isn’t about memorizing dates. It’s about reducing stress and improving outcomes. When tax planning becomes part of your routine rather than a seasonal scramble, decisions become clearer and more intentional.

At Illumination Wealth, we help clients turn deadlines into opportunities and ensure tax planning supports broader financial goals throughout the year. Contact us today to get started on your annual tax plan.