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Mid-Year Is Where Strategy Starts: Making the Most of Your Tax Planning 

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Why Mid-Year Matters More Than Year‑End

Most taxpayers wait until year-end—or even April—to assess their tax posture. By then, your planning options are limited. Mid-year is different: with half the year’s data available and enough time left to act, you have a powerful window to make meaningful adjustments. 

Whether you’re an individual earner, business owner, or retiree, a mid-year tax review: 

  • Helps reduce tax liabilities before it’s too late
  • Identifies opportunities for savings across deductions, credits, and contributions
  • Prevents underpayment penalties or refund delays 

Your Mid-Year Audit: What to Review Now

Mid-year is the ideal moment to perform a mini tax audit on your financial year-to-date. Here’s what to focus on: 

Income & Expense Forecast 

  • Tally income year-to-date and project through December 
  • Identify one-time events like bonuses or windfalls 
  • Separate recurring income vs. fluctuating revenue streams 


Withholding & Estimated Payments 

  • W-2 earners: revisit your W-4 via the IRS Withholding Estimator 
  • 1099 or self-employed: adjust your Q3/Q4 estimated payments to avoid underpayment penalties 


Retirement and HSA Contributions 

  • Review 401(k), IRA, SEP-IRA, or Solo 401(k) status 
  • Max out HSA contributions if you’re in a high-deductible health plan (HDHP) 
  • Use mid-year contributions to catch up, rather than waiting until December 


Deductions, Credits & Pre‑Payments 

  • If itemizing, consider timing mortgage payments or property tax early 
  • Make charitable contributions now to spread them out 
  • Check eligibility for education or child tax credits with adjusted income projections 


Investment Gains/Losses & Cost Segregation 

  • Rebalance your portfolio and harvest gains or losses for tax optimization
  • Rental property owners may consider a cost segregation study to accelerate depreciation
  • Evaluate capital gains tax strategy based on current bracket and income phase-outs 

Business Owner & Entrepreneur Strategies

If you’re running a business—especially as a sole proprietor, LLC, or S Corp—your mid-year tax review should be even more proactive. 

Entity Structure Review 

  • Evaluate if your current structure (LLC, sole prop, S Corp) still serves your tax goals 
  • If profits have grown, you might benefit from electing S Corp status and taking a reasonable salary to reduce self-employment tax 


Depreciation & Payroll Planning 

  • Plan Section 179 or bonus depreciation on business equipment purchases 
  • Consider setting up an accountable plan for reimbursing employees tax-free 
  • Review payroll thresholds for key credits and retirement plan eligibility 

Key Tax Moves You Can Still Make

There’s still time to act on smart tax-saving strategies: 

  • Roth conversions: Convert part of your traditional IRA to Roth in lower-income years 
  • QCDs: For those 70½+, qualified charitable distributions reduce AGI and meet RMD rules 
  • Donor-Advised Funds: Bunch multiple years of charitable giving into a single tax year to exceed the standard deduction 
  • 529 Plan Contributions: Fund education savings for children or grandchildren and take potential state tax benefits 

Final Thoughts 

Mid-year planning isn’t just a touchpoint—it’s a turning point. With focused strategy, flexible tools, and expert guidance, you can make the next six months your most tax-efficient yet. 

Need help making it happen? Contact our team at A SAM LLP for a personalized mid-year planning session. We’ll walk you through the numbers, help you take action, and keep your financial strategy on track for year-end. 

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