As we move into June, many business owners are focused on serving clients, growing revenue, and managing day-to-day operations.
Unfortunately, taxes are often pushed to the bottom of the priority list until a surprise bill arrives.
One of the most common issues I see is business owners who owe taxes every year but never make estimated tax payments throughout the year.
Estimated Tax Payments Are Due June 15
If you owed taxes when you filed your return, there’s a good chance you should be making quarterly estimated tax payments.
This isn’t just for business owners.
Estimated payments may apply to:
- Self-employed individuals
- Independent contractors
- Investors with significant income
- Retirees with insufficient withholding
- Anyone who consistently owes taxes at filing time
The IRS operates on a “pay as you go” system. If too little tax is paid throughout the year, penalties and interest may be assessed—even if you pay the balance in full when you file your return.
The second-quarter estimated payment deadline is June 15.
If you’re unsure whether you should be making estimated payments, now is the time to find out—not next April.
Is Your Business Structure Costing You Money?
Another issue I frequently uncover is business owners operating under the wrong entity structure.
Many successful businesses continue operating as:
- Sole proprietorships
- Single-member LLCs
- Multi-member LLCs
without ever evaluating whether an S Corporation election could reduce their tax liability.
For the right business, an S Corporation can create significant self-employment tax savings.
However, an S Corporation is not a magic tax solution.
To be effective, it requires:
- Proper bookkeeping
- Payroll compliance
- Reasonable compensation planning
- Ongoing tax strategy
- Timely tax filings
That’s why tax planning should never happen in isolation. The structure, bookkeeping, payroll, and tax return all need to work together.
Don’t Forget State Compliance Requirements
One area that often catches business owners off guard is state compliance.
Many states require annual reports or business registrations that are completely separate from your tax return.
Missing these filings can result in:
- Penalties
- Administrative fees
- Loss of good standing
- Difficulty obtaining financing
- Issues renewing licenses or permits
Just because your tax return is filed doesn’t mean all of your business compliance obligations have been satisfied.
Tax Planning Is a Year-Round Activity
The business owners who experience the fewest tax surprises aren’t necessarily the ones making the most money.
They’re the ones who review their numbers regularly throughout the year.
At Rae’s Accounting, we don’t believe tax planning should be a once-a-year conversation.
We work with business owners throughout the year to:
✓ Review profitability
✓ Adjust estimated tax payments
✓ Evaluate entity structure
✓ Monitor compliance requirements
✓ Identify tax-saving opportunities before year-end
Because once December 31 passes, many tax planning opportunities disappear.
As I often tell clients:
“I’m not interested in giving you a history lesson after the year is over. I’d rather help you write a better financial story before the year ends.”
If you haven’t reviewed your tax situation since filing season, now is the perfect time to start the conversation.
Agent Rae is a proactive tax planning partner unlike the reactive history lesson accountants you may be used to.
Schedule a consultation today and let’s see if you’re on track—or headed toward an avoidable tax surprise.
