Taxes

What you owe when nobody withholds it for you. Self-employment tax, quarterly payments, 1099 forms, deductions, and the deadlines that matter.

  • Do You Have to File? The $400 Rule for Self-Employed Americans

    If your net self-employment earnings for 2026 are $400 or more, you must file a US federal tax return. That threshold sits far below the standard deduction, and it catches people who earned almost nothing. Everything on this page is United States federal tax, for people filing a US return. Your state may have its…

  • What Actually Triggers an IRS Audit When You Work for Yourself

    The IRS examined 0.3% of individual income tax returns filed for tax year 2021, the most recent year past the normal statute of limitations. In the bands where most freelancers file, the rate was 0.2% — two returns in every thousand. What raises your odds is rarely that you work for yourself. It is a…

  • How to Actually Pay Your Estimated Taxes

    Use IRS Direct Pay. It is free, it needs no account, it takes about three minutes, and it pulls the money straight out of your checking account. On a $5,500 payment the comparison is not close. Direct Pay costs nothing. A debit card costs $2.10 or $2.15. A credit card costs $96.25 or $101.75, depending…

  • Do You Owe Sales Tax on Freelance Work?

    Most freelancers who sell pure services owe no sales tax. Consulting, writing, coaching, design labor — most states do not tax them at all. What catches people is digital products. And this is a different tax from the two you already know. Income tax and self-employment tax come out of your profit. Sales tax was…

  • Your First Year Freelancing: The Tax Checklist

    Five things decide your first year, and the rest is detail. Open a second bank account and move 25% to 30% of every payment into it the day the money lands. Get an EIN from irs.gov, free, in about ten minutes. Record every business expense from your first dollar. Pay the IRS four times a…

  • Why a 50% Deposit Is the Fix That Works

    Ask for 50% before you start. Not mainly because the money is better in your account than in theirs, though it is. Ask because of what it does to the client. A stranger who has paid you nothing is deciding, quietly, every week, whether this project still deserves their attention. A client who has already…

  • Business Expenses Are Not Itemized Deductions

    Business expenses are not itemized deductions. They come off on Schedule C, before your adjusted gross income is even calculated, and you get every one of them whether you take the standard deduction or itemize. Taking the $16,100 standard deduction does not cost you your laptop, your software, or your mileage. These are two different…

  • Paying Yourself Is Not a Business Expense

    Moving money from your business account to your personal account is a draw, not an expense. It does not reduce your profit, it does not appear anywhere on Schedule C, and it does not lower your tax by a dollar. As a sole proprietor you are taxed on what the business earned, not on what…

  • An Extension Gives You Time to File, Not to Pay

    Form 4868 buys you six more months to file. Your 2025 return moves from April 15, 2026 to October 15, 2026. It does not move the payment. Whatever you owed was due April 15, and interest has been running on it since that day. What moves and what does not Two deadlines sit on April…