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Common Tax Mistakes That Could Cost You Money (and How to Avoid Them)

canfield246

Updated: Jan 9

Taxes can feel like a minefield for small business owners.


While you’re focused on running your business, it’s easy to overlook details that lead to missed savings, penalties, or extra stress.


The good news?

Most tax mistakes are avoidable once you know what to watch for.


Let’s break down the most common tax mistakes small business owners make—and how you can avoid them to save time, money, and peace of mind.


1. Not Keeping Accurate Records


The Mistake: 

Many business owners wait until tax season to organize their receipts, invoices, and expenses. By then, details are forgotten, receipts are lost, and deductions are missed.


Why It Matters: 

Poor record-keeping can mean:

  • Overpaying on taxes because you missed deductions.

  • Underreporting income, leading to IRS penalties.

  • Added stress when filing your return.


How to Avoid It:

  • Keep all receipts, invoices, and expense records organized year-round.

  • Use bookkeeping software or hire a bookkeeper to stay on top of transactions.

  • Regularly reconcile your accounts to ensure accuracy.


Pro Tip: 

If you don’t want to deal with this yourself, hire a professional bookkeeper. Accurate records save you more money than they cost.


2. Missing Out on Deductions


The Mistake: 

Business owners often don’t realize what they can deduct—things like home office expenses, mileage, or business meals. Others worry they’ll “trigger an audit” and skip valid deductions.


Why It Matters: 

Every missed deduction means you’re paying more in taxes than you should.


How to Avoid It:

  • Know what qualifies as a business expense (supplies, software, travel, meals, etc.).

  • Track all expenses carefully throughout the year.

  • Work with a tax professional who can identify overlooked deductions.


Example: 

If you work from home, you may qualify for the home office deduction, which can save you hundreds of dollars each year.


3. Filing Late (or Not at All)


The Mistake: 

Some business owners put off filing because they’re unprepared or overwhelmed. Others don’t file at all, assuming they’ll “figure it out later.”


Why It Matters: 

Filing late or missing deadlines leads to penalties and interest that add up fast.


How to Avoid It:

  • Know your tax deadlines:

    • Quarterly Taxes: Due four times a year for most small business owners.

    • Annual Tax Return: Typically due on April 15.Click here to see all tax deadlines

  • Set reminders for key deadlines.

  • File for an extension if needed—but remember, this doesn’t delay payments owed.


4. Mixing Personal and Business Finances


The Mistake: 

Using the same bank account or credit card for both business and personal expenses is one of the most common errors small business owners make.


Why It Matters:

  • It complicates your bookkeeping and tax preparation.

  • It increases the chance of missing deductions.

  • It could lead to IRS scrutiny during an audit.


How to Avoid It:

  • Open a separate business bank account and credit card.

  • Only use business accounts for business expenses.

  • Categorize all transactions properly to stay organized.


Example: 

If you buy office supplies with a personal card, it’s easy to forget to include that expense as a deduction. Keeping finances separate eliminates this problem.


5. Misclassifying Employees and Contractors


The Mistake: 

Confusing independent contractors with employees—or vice versa—can cause major tax issues.


Why It Matters:

  • Misclassifying workers can lead to IRS penalties, unpaid taxes, and back wages.

  • Employees require payroll taxes, while contractors pay their own taxes.


How to Avoid It:

  • Understand the IRS guidelines for employees vs. contractors.

    • Employees: Work set hours under your supervision. You withhold payroll taxes.

    • Contractors: Work independently. You don’t withhold taxes but issue a 1099.

  • If unsure, ask a tax professional for guidance.


6. Ignoring Estimated Quarterly Taxes


The Mistake: 

Many business owners assume they can wait until April to pay taxes, only to find out they owe penalties for not making quarterly payments throughout the year.


Why It Matters: 

If you owe more than $1,000 in taxes for the year, you’re required to pay in installments each quarter. Missing these deadlines means penalties and interest.


How to Avoid It:

  • Estimate your tax liability with help from a tax professional.

  • Pay taxes in four quarterly installments: April 15, June 15, September 15, and January 15.

  • Use bookkeeping software to project your tax obligations in advance.


7. Not Consulting a Tax Professional


The Mistake: 

Many business owners try to “DIY” their taxes, believing it saves money. But without a professional, it’s easy to miss deductions, make mistakes, or file incorrectly.


Why It Matters: 

A tax professional can:

  • Identify deductions and credits you may not know about.

  • Ensure you’re compliant with all IRS rules.

  • Save you money by minimizing your tax liability.


How to Avoid It:

  • Work with a tax professional year-round, not just during tax season.

  • Use their expertise to plan ahead and make smarter financial decisions.


Example: 

Tax laws change regularly, and a professional ensures you take advantage of new opportunities to save money.


Avoid Tax Mistakes and Save More


Taxes don’t have to be stressful.

By avoiding these common mistakes and staying proactive, you can:

  • Save money by maximizing deductions.

  • Avoid penalties and interest.

  • Have peace of mind knowing your finances are in order.


Don’t let tax mistakes cost you money. 

Let’s make sure you’re saving every dollar you can.


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