Year-End Tax Planning Guide for Small Business Owners & Roofing Contractors

As the year comes to a close, November and December are the most important months for tax planning.

You still have enough time to make strategic financial moves — and you now have a clear picture of what your income and deductions look like for 2025.

Here are 10 smart year-end tax strategies to help business owners reduce tax liability, stay compliant, and enter 2026 financially prepared.

1. Maximize Retirement Contributions (If Eligible)

Business owners with access to workplace retirement plans may still have time to increase contributions before December 31.
Higher contributions can:

  • Lower taxable income
  • Boost long-term retirement savings
  • Help business owners take advantage of employer matching (if offered)

Even small increases in November and December can make an impact.

2. Consider a Mega Backdoor Roth (Advanced Strategy)

For high-income earners with a workplace 401(k) that allows after-tax contributions:

You may be able to contribute beyond the standard limit and then roll those funds into a Roth account — allowing for tax-free growth in the future.

This strategy only works if your plan permits after-tax contributions and in-service rollovers.

3. Backdoor Roth Conversion

If your income is too high for a direct Roth IRA contribution, a Backdoor Roth may be an option.
It involves:

  1. Making a non-deductible contribution to a Traditional IRA
  2. Converting it to a Roth

Important:
This strategy generally works best when you have no balance in Traditional, SEP, SIMPLE, or rollover IRAs by December 31, or the conversion may become taxable.

4. Optimize Charitable Giving

If you’re planning to donate before year-end, consider gifting appreciated stock instead of cash.

Benefits include:

  • Deducting the fair market value
  • Avoiding capital gains tax
  • Reinvesting cash at a higher cost basis

This can be more tax-efficient than donating cash alone.

5. Use Tax-Loss Harvesting (If Applicable)

If you have investments showing a loss, selling them before year-end can help:

  • Offset capital gains
  • Reduce taxable income (up to $3,000 per year)

Just remember the wash sale rule — you cannot buy the same or “substantially identical” security within 30 days before or after the sale, or the loss won’t count.

6. Tax-Gain Harvesting for Lower-Income Years

If your taxable income falls within the 0% long-term capital gains bracket, you may be able to:

  • Sell appreciated securities
  • Realize gains tax-free
  • Immediately buy them back to increase cost basis

This strategy works best when no state capital gains tax applies.

7. Max Out Your HSA (If You Qualify)

Health Savings Accounts offer triple tax benefits:

  • Tax-deductible contributions
  • Tax-free growth
  • Tax-free withdrawals for medical expenses

Many business owners use HSAs to plan for future healthcare costs while reducing current-year taxable income.

8. Review Your Business Entity Structure

Your business structure can significantly affect taxes — especially if profits are increasing.

For business owners with net income above $100,000, electing S-Corporation status may:

  • Reduce self-employment taxes
  • Allow income to be split between salary and distributions

However, S-Corps also include payroll and compliance requirements, so analysis is essential before making a change.

9. Track and Categorize Business Expenses

Many small business owners overpay taxes simply because expenses are not properly recorded.

Commonly missed deductions include:

  • Business meals
  • Software and subscriptions
  • Equipment purchases
  • Home office expenses
  • Entity filing fees

Keeping clean books throughout the year — not just at tax time — helps avoid missed deductions and inaccurate quarterly estimates.

10. Year-End Gifting Rules

In 2025, individuals can gift up to $19,000 per person ($38,000 for married couples) without affecting lifetime estate exemptions.

While this does not reduce current income taxes, it can support long-term wealth-transfer planning — especially for individuals in states with low estate thresholds.

✅ Final Thoughts

Year-end is the best time to:

  • Reduce taxable income
  • Capture deductions before it’s too late
  • Plan proactively instead of reacting at tax filing time

At Freedom From Accounting, we help business owners stay ahead — not overwhelmed.

📅 Need Year-End Tax Guidance?

Schedule your consultation now and we’ll help you:

✅ Review your 2025 projections
✅ Identify tax-saving opportunities
✅ Avoid costly last-minute mistakes
✅ Start 2026 financially confident

👉 Book your strategy call