Problem 1: Not Making Estimated Tax Payments
This is the number one problem I see with self-employed people. You earn money throughout the year, spend it, and then realize in April that you owe $30,000 in taxes with no money to pay it. The IRS expects quarterly estimated tax payments. If you do not make them, you owe the tax plus an estimated tax penalty.
The fix is simple in theory but hard in practice. Set aside 25 to 30 percent of every dollar you earn. Put it in a separate account. Make quarterly payments on time. If you are already behind, a tax attorney can negotiate a payment plan while you get current on estimated payments going forward.
Problem 2: Mixing Personal and Business Expenses
When you use your business account for personal expenses and your personal account for business expenses, you create a recordkeeping nightmare. If the IRS audits you, they will disallow deductions you cannot substantiate. Worse, commingling funds can jeopardize your liability protection if you operate through an LLC or corporation.
Problem 3: Misclassifying Workers
Treating employees as independent contractors saves money on payroll taxes, workers compensation, and benefits. But if the IRS determines that your contractors are actually employees, you owe all the back employment taxes plus penalties. The IRS looks at factors like control over how the work is performed, who provides the tools, and whether the worker can profit or lose money.
Problem 4: Falling Behind on Payroll Taxes
When cash flow gets tight, business owners sometimes use payroll tax withholdings to cover operating expenses. This is the fastest way to get in serious trouble with the IRS. Trust fund taxes carry personal liability through the trust fund recovery penalty. The IRS can hold you personally responsible even if the business is a corporation.
Problem 5: Inadequate Record Keeping
If you cannot prove a deduction, you do not get the deduction. It is that simple. The IRS requires adequate records for all business expenses. Receipts, invoices, bank statements, mileage logs, travel records. The burden of proof is on you. A shoebox full of receipts is better than nothing, but a proper bookkeeping system is better than a shoebox.