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The Tax Missteps That Cost Small Business Owners the Most

Most tax problems have little to do with the return itself — and everything to do with the months leading up to the preparation of it.

Most small business owners don't have a tax problem. They have a "nobody told them until it was too late" problem. By the time a return is prepared, nearly every meaningful chance to shape the outcome is already behind you. The most expensive tax mistakes aren't made in April — they're made in the months before when no one is thinking about taxes at all.

It's a Timing Problem, Not a Tax Problem

Planning is a year-round activity. The decisions that actually lower a bill — how you pay yourself, when you buy equipment, how your business is structured — have to happen while the year is still open. Filing season is where those decisions show up on paper, not where they get made. If the only tax conversation you have is the one where you sign the return, you are seeing the scoreboard after the game is over.

The Traps That Catch Owners Off Guard

Depending on your business structure, there are traps that can catch you off guard. For example, as an S Corporation, a common one is the S-corporation salary. Paying yourself little or nothing to avoid payroll tax works right up until the IRS asks whether that figure is reasonable for the work you do. The answer to that question is a defensible number — what you'd pay someone else to do your job — not zero. Just as common for any small business structure is leaving money on the table by overlooking deductions like the Qualified Business Income deduction, one of the larger benefits available to pass-through owners, where structure and planning make a real difference.

The return in April is the last ten percent of the value. The other ninety percent is the conversations that happen all year.

Don't Fear the Envelope

Another area that I see small business owners either don't pay attention to or they do and there is panic: A letter from the IRS. It rarely is the emergency it feels like. The large majority are routine — a math notice, a misapplied payment, a request for a form. The right response is simple: don't panic, don't ignore it, and read what it actually says. The owners who stay calm are usually the ones who have someone in their corner year-round, not just at filing time.

That is the real dividing line — between a preparer who hands you a finished return and an advisor who helps you make decisions before they're locked in. If you're not sure which one you have, that's worth a conversation of its own.




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Learn more about the author Samantha M. Besnoff, CPA



This article is general information for educational purposes and is not tax, legal, or financial advice for your specific situation. Please consult a financial professional about your circumstances.


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