June 17, 2025

Mid-Year Tax Strategy Checklist

Your proactive guide to minimize liabilities and maximize value.

1. Review Revenue vs. Forecast

  • Are you ahead or behind projections?

  • Do Q1 and Q2 actuals suggest a revised revenue target?

2. Adjust Estimated Tax Payments

  • Have you recalculated your Q3 and Q4 estimated taxes based on actual performance?

  • Avoid overpayment or underpayment penalties by aligning with real-time numbers.

3. Evaluate R&D Tax Credit Eligibility

  • Are you developing technology, internal systems, or new products?

  • Ensure documentation is in place to claim credits for qualifying work.

4. Analyze Entity Structure

  • Is your current business structure (LLC, S-Corp, C-Corp) still optimal for your tax goals and capital plans?

  • Should you consider a restructuring based on growth, investment, or ownership changes?

5. Optimize Owner Compensation

  • Is your mix of salary, dividends, or distributions structured tax-efficiently?

  • Consider the implications for self-employment taxes, retirement contributions, and QBI deductions.

6. Plan for Capital Raises or Exits

  • Are your financials and tax returns clean and investor-ready?

  • Are you minimizing audit risk and maximizing your valuation narrative?

7. Review Retirement and Benefit Contributions

  • Have you fully utilized available retirement plan contributions (SEP IRA, Solo 401k, etc.)?

  • Can you structure benefits to reduce taxable income?

8. Assess State and Local Tax (SALT) Exposure

  • Are you expanding into new states?

  • Have you reviewed nexus issues and multi-state filing requirements?

9. Integrate Personal and Business Planning

  • Are there opportunities to shift income or expenses for better personal tax positioning?

  • Have you planned for equity grants, buybacks, or liquidity events?

10. Schedule a Strategic Tax Review

  • Don’t wait until Q4 or worse—March. Now’s the time for proactive planning.

[Download the Checklist]

📆 Book Your Mid-Year Review


Now’s the time to catch opportunities—and correct courses if needed. Let’s revisit your numbers, your goals, and your roadmap to minimize liability and maximize growth.

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