We're almost halfway through the year, and if you're a business owner, this is your moment to recalibrate.

June is a critical checkpoint: quarterly tax payments are due, your books are (hopefully) up to date, and you’ve still got time to find ways to save on your 2025 tax bill.

We put together a simple, tactical checklist to help you make smart moves now, before the second half of the year slips away. 

Whether you’re finalizing Q2 estimates or looking for ways to trim your tax liability, this guide breaks down exactly what to focus on.

‍

Quarterly Tax Estimates

• Calculate Q2 estimated tax payment due June 16,2025
• Verify you've met safe harbor requirements: (100%-110% of last year's liability)
• Set up automatic transfers to a dedicated tax savings account
• Review Q1 payment to ensure it was adequate
• Project Q3 and Q4 payments based on updated income forecasts
• Check state and local tax payment requirements and deadlines
• Consider impact of any business changes on estimated payments

Financial Assessment

• Review year-to-date profit and loss statements
• Compare current year performance to previous years
• Update revenue projections for remainder of year
• Analyze cash flow patterns and identify potential issues
• Review accounts receivable and collectability
• Schedule a mid-year meeting with your tax professional

Business Structure Optimization

• Review current entity structure for tax efficiency
• If LLC, evaluate benefits of S-Corp election. Try our S-Corp Savings Calculator.
• For S-Corps, assess reasonable salary vs. distributions ratio
• Check compliance with all entity-specific tax requirements

Income & Expense Management

• Any opportunities to accelerate deductible expenses?
• Consider deferring income to next year if beneficial
• If near income thresholds, plan strategies to maximize QBI benefit
• Plan major equipment or asset purchases strategically
• Maintain vehicle logs and mileage tracking for deductions
• Reconcile bank and credit card accounts through current month

Retirement Planning

• Calculate maximum allowable retirement plan contributions*
• For Solo 401(k)s, review both employee and employer contribution limits
• Evaluate SEP IRA vs. Solo 401(k) options for your situation
• Consider the pros/cons of Health Savings Account (HSA)
• Review self-employed health insurance deduction eligibility
• Plan year-end retirement contributions based on projected income

*You have until April 15, 2026 to fund retirement accounts for 2025, but the accounts must be open before December 31, 2025.

‍

Mid-year is your window of opportunity. Get your books in order, adjust your estimates, and make a few smart moves now to avoid surprises (and save money) come tax time.

This checklist is built to help you take action, not just file paperwork. Use it to simplify, strategize, and set yourself up for a stronger second half of 2025.

Your future self will thank you.

‍