Why Every Business Owner Needs a Mid-Year Financial Checkup (and How to Start

As a business owner, it’s easy to get so caught up in the day-to-day operations that you forget to zoom out and review the bigger financial picture. But mid-year — right around May through July — is one of the most critical times to check in on your financial health.

A mid-year financial review isn’t just a best practice — it could be the difference between meeting your goals or scrambling to catch up at year-end. Here's why you can't afford to skip it this year, and what to focus on.

1. Tax Changes Are Coming in 2025

Many of the tax benefits created under the Tax Cuts and Jobs Act (TCJA) are set to expire after 2025. That means your current tax strategy might not serve you for much longer. Now is the time to:

• Review your entity structure (S-corp, LLC, etc.) to ensure it still makes sense.

• Accelerate deductions or investments if changes to tax rates will impact your bottom line.

• Plan ahead for higher individual and business tax rates that could be coming.

  
  

2. Cash Flow is Tightening Across Industries

Whether due to inflation, increased overhead, or slower client payments, cash flow issues are hitting small businesses hard in 2025. A mid-year checkup can help you:

• Reforecast revenue and expenses for the rest of the year.

• Identify and plug cash leaks.

• Restructure debt or secure financing before it becomes a crisis.

  
  

3. Payroll and Employee Costs Need a Fresh Look

Labor costs have shifted significantly over the past few years, and many owners are feeling the squeeze. Mid-year is the perfect time to:

• Audit your payroll processes for efficiency and compliance.

• Reassess contractor vs. employee classifications.

• Adjust benefits or wages to stay competitive (without breaking the bank)

  
  

4. Bookkeeping and Records May Need Cleaning Up

Too often, business owners don't realize their books are messy until it’s time to file taxes — and by then, it's an expensive fix. A mid-year financial review ensures:

• Transactions are correctly categorized.

• Outstanding invoices or bills are addressed.

• You're ready for a smoother year-end close.

  
  

5. Tax Planning Starts Now (Not in December)

Waiting until year-end to start thinking about taxes often leads to missed opportunities. A mid-year review can:

• Estimate your 2025 tax liability while there’s still time to lower it.

• Strategically time major purchases or investments.

• Maximize retirement plan contributions or other deductions.

  
  

How to Start Your Mid-Year Financial Checkup:

• Schedule a meeting with your CPA (we can help!).

• Gather your latest financial statements.

• Identify any major changes (hiring, big contracts, business pivots).

• Discuss your goals for the rest of the year — and beyond.

  
  

If you don't have a trusted CPA partner or feel like your current advisor isn’t proactive, now is the perfect time to find someone who will help you think ahead, not just look backward.

At Simon Accounting Services (SAS), we specialize in helping business owners like you navigate these critical moments with clarity and confidence.

Book your consultation today to make sure your 2025 story ends on a high note — not a scramble.

Schedule Your Mid Year Checkup with SAS!