Seasonal Tax Considerations for Business Owners

As the seasons change, so do the tax planning opportunities and responsibilities for business owners. Whether you operate a law firm, manage real estate investments, or oversee family wealth, staying ahead of seasonal tax considerations can help you avoid surprises and maximize your returns.

Here’s a seasonal breakdown to keep in mind throughout the year.

Spring: File or Extend and Make Estimated Payments

Tax season is in full swing by March and April:

  • March 17: Deadline for S corporation and partnership returns (or extensions).

  • April 15: Deadline for C corporations and individual returns, plus the first quarterly estimated tax payment.

Spring is also a smart time to revisit compensation strategies. Real estate clients might benefit from cost segregation studies. Law firm partners may want to examine guaranteed payments and profit allocations.

Summer: Mid-Year Check-In and Strategic Planning

Summer offers a window for proactive tax planning without looming deadlines:

  • Conduct a mid-year review: Are revenues tracking ahead of projections? Do you need to adjust estimated payments?

  • Evaluate retirement contributions: Consider maximizing SEP-IRA or 401(k) contributions before year-end.

  • Explore tax credits: Real estate investors may qualify for energy-efficient building credits; law firms investing in legal tech may be eligible for R&D incentives.

For high-net-worth individuals, this is a good time to revisit estate and gift tax strategies.

Fall: Get Organized for Year-End

As the year winds down, take steps to finish strong:

  • Finalize major purchases: Equipment and other capital expenses may offer tax benefits if acquired before year-end.

  • Review income timing: Accelerating or deferring income and expenses can impact your tax liability.

  • Schedule your year-end tax planning meeting: Don’t wait until December to strategize—earlier planning allows more flexibility.

Winter: Prepare for Year-End Reporting and Deadlines

The beginning of the year is a time for reflection—and action. January and February are heavy on compliance tasks:

  • Issue W-2s and 1099s: Ensure all wage and contractor payments are documented and distributed by January 31.

  • Gather year-end financials: Accurate books are essential for preparing your business returns and planning for the year ahead.

  • Review entity structure: Consider whether your business entity is still the most tax-efficient setup, especially if you experienced growth or major changes.

For real estate businesses, now is a good time to review depreciation schedules and passive activity rules. For law firms, ensure trust accounting is reconciled and ready for reporting. High-net-worth individuals with closely held businesses may need to evaluate distributions and gifting strategies.

Need Help Planning Seasonally?

We specialize in serving the unique tax needs of real estate professionals, law firm partners, and high-net-worth individuals. Our advisors provide proactive, year-round guidance so you can stay focused on growing your business.

Ready to plan ahead?

Contact us to schedule your seasonal tax review.