Experts Reveal 3 Common Tax Mistakes That Could Cost You Big

As tax season comes to a close each year, many Americans rush to meet the April 15 deadline and celebrate when they received a big refund. But according to tax experts, these popular strategies might actually be costing you money.

Mark J. Kohler, M.PR.A., C.P.A., J.D.,Founding and Senior Partner at KKOS Lawyers, specializing in tax, legal, wealth, estate, and asset protection planning and Timothy Wingate Jr., an IRS-certified tax specialist and founder of G+F Business & Financial Consulting, say taxpayers often fall for three common traps — and correcting them can lead to smarter financial decisions all year long.

Here’s what people get wrong about taxes and how you can take a more strategic approach.

1. Filing By April 15 Isn’t Always Necessary

While the April 15 deadline is real, filing your return on that day isn’t always required — or even wise.

“Contrary to popular opinion, it’s not the end of the world if you don’t file your personal 1040 tax return by April 15,” Kohler said. “In fact, it can be very strategic to not file and instead submit an extension. Getting an extension gives you time to get all your records in order.”

Timothy Wingate Jr., an IRS-certified tax specialist and founder of G+F Business & Financial Consulting, agrees — and offers practical advice for how to do it right.

Here’s how to file an extension the smart way, according to Wingate:

• Mail Form 4868. “File an extension by mail with the form 4868. Make sure you send it in certified mail with a return receipt,” Wingate says.
• Work with a pro. “You can file an extension with a tax professional who uses ProConnect Tax Online to make sure it is completed correctly and timely.”
• Consider paying up front. “If you owed money to the IRS last year, you can pay the same amount by the tax deadline to avoid any penalties when filing your extension.”
• Explore a payment plan. “If your tax liability has been assessed, you can request an installment agreement with the IRS to pay them back over time.” Click here to apply.

Filing an extension gives you until October 15 to submit your return—but remember, it doesn’t delay the deadline to pay any taxes owed. To avoid penalties or interest, it’s smart to send a payment by April 15, even if your paperwork isn’t ready.

2. A Big Refund Isn’t Always A Good Thing

Most people celebrate a large refund check — but Kohler says that mindset needs to change.

“Our number one cost in life is taxes,” he said. “If we can minimize that, we can deploy that money in other areas that make us money. That’s the concept of tax planning.”

Rather than aiming for a big refund, aim to owe nothing — and keep more of your paycheck throughout the year.

Talk to a tax advisor about adjusting your withholdings, contributing to retirement accounts, or making strategic investments to reduce your taxable income.

3. Not Running Your Side Hustle Like A Business

With nearly 40% of Americans working a side hustle, treating that income seriously is more important than ever.

“Side hustles aren’t just income streams — they’re tax planning opportunities,” Kohler said. “But too many people miss out because they don’t keep records or claim expenses.”

“Keep separate accounts, track all expenses, and consult a tax professional,” he said. “That way, you can legally deduct business expenses and potentially lower your overall tax bill.”

Possible Deductions Include:

• Home office expenses
• Internet and software costs
• Mileage and vehicle expenses
• Equipment and supplies
• Business travel and meals

Accurate record-keeping is essential to claim these deductions — and to protect yourself in case of an audit.

Bottom Line

Don’t wait until tax season to think about your tax strategy. Avoiding these common mistakes — filing blindly by April 15, celebrating big refunds, and ignoring your side hustle’s business status — can help you keep more of your money.

Instead, work with a trusted tax advisor, file smarter (not faster), and take full advantage of deductions and planning strategies year-round. Your future finances will thank you.