We’re officially halfway through the year—and that means it’s the perfect time to pause, assess, and fine-tune your tax strategy.

Too many business owners wait until the last quarter (or worse, tax season) to think about taxes. But by then, many of the best money-saving strategies are already off the table.

A proactive mid-year tax review puts you in control, helping you reduce surprises, improve cash flow, and set yourself up for a smoother—and more profitable—year-end.

At Bernstein Tax Group, we guide entrepreneurs and high earners through tax-smart decision-making all year long. Here’s your go-to checklist for a successful mid-year tax tune-up.

✅ Review Year-to-Date Income & Profitability

Start by pulling your YTD profit and loss (P&L) statement. How much income have you earned? How much profit is left after expenses?

Key questions to ask:

• Am I on track to earn more or less than last year?
  

• Have my expenses or margins changed significantly?
  

• Is my tax liability likely to increase?

Understanding your financial trends now can help you make smart decisions about spending, saving, and estimated tax payments in Q3 and Q4.

✅ Evaluate Your Estimated Tax Payments

If you're self-employed or own a business, you’re likely required to make quarterly estimated tax payments. Underpaying can result in penalties—and overpaying means giving the IRS an interest-free loan.

Mid-year is the time to:

• Recalculate your estimated tax liability based on actual YTD income
  

• Adjust your Q3 and Q4 payments accordingly
  

• Plan for cash flow to meet September 15 and January 15 deadlines

We help clients run projections to avoid underpayment penalties and make more accurate quarterly payments.

✅ Maximize Available Deductions (Before It’s Too Late)

Many deductions and tax strategies require action before December 31. Mid-year gives you time to plan and capture those savings.

Key deductions to review:

• Home office expenses
  

• Vehicle and mileage logs
  

• Professional development and business education
  

• Business meals and travel
  

• Equipment purchases that may qualify for Section 179 expensing
  

• Retirement contributions (SEP IRA, Solo 401(k), etc.)

Document everything now. Waiting until tax season means you risk missing deductions due to lost receipts, forgotten expenses, or missed deadlines.

✅ Revisit Your Business Structure

Your legal entity type plays a huge role in how you're taxed. As income grows, certain structures may no longer be ideal.

Ask yourself:

• Am I still operating as a sole proprietor when I could benefit from an S Corporation?
  

• Is my LLC structured properly to maximize deductions and minimize self-employment tax?
  

• Should I consider bringing on a partner or splitting income strategically?

Changes made before year-end can impact your 2025 tax return. We can help you assess whether a restructure or conversion could save you thousands.

✅ Plan for Retirement Contributions Now

Tax-advantaged retirement accounts are powerful wealth-building tools—and they offer significant tax benefits for business owners.

Mid-year is the best time to:

• Choose the right plan for your business (SEP IRA, Solo 401(k), SIMPLE IRA, etc.)
  

• Set contribution goals for the rest of the year
  

• Allocate cash flow toward those contributions gradually

Waiting until April 15 to fund your retirement can put unnecessary strain on your business. Planning now gives you flexibility and peace of mind.

✅ Confirm You’re In Compliance

Avoid audit triggers by ensuring all your tax and business compliance boxes are checked.

Things to double-check:

• Have you filed all necessary payroll tax reports and made payments on time?
  

• Are your W-9s and 1099s properly collected for contractors?
  

• Are your sales tax filings and business licenses up to date?
  

• Are your books accurate and reconciled?

Clean books and proactive recordkeeping reduce audit risk and make tax filing a breeze.

✅ Schedule a Mid-Year Tax Strategy Session

The best part of a mid-year review? You still have time to act.

Working with a tax strategist now allows you to:

• Make better decisions with real numbers
  

• Reduce taxable income before the year ends
  

• Avoid costly mistakes or surprises
  

• Save significantly more by leveraging deductions and smart planning

At Bernstein Tax Group, we help clients build tax strategies that work in real time—not just at tax time.

📞 Schedule your free mid-year consultation and let’s optimize your plan together. We guarantee you’ll save more than our fees—or you don’t pay.

→ Book your session today and take control of your tax strategy before Q4 hits.