Guides
Everything we know about self-employed taxes, written for humans — honest about trade-offs, dated where facts can age, and linked to the sources throughout.
How quarterly estimated taxes work — the whole system, plainly
Who has to pay estimated taxes, how the four deadlines actually work, what the safe-harbor rule protects you from, and how the math fits together.
How to actually pay estimated taxes — Direct Pay, EFTPS, and the paper trail
The mechanics of sending money to the IRS: which payment method to use, how to label the payment correctly, and the records that save you in April.
LLC, S-corp and self-employment tax — the honest break-even
What an LLC actually changes about taxes (nothing), how the S-corp saving really works, what it costs, and the profit level where the math starts working.
Self-employment tax, explained — where 15.3% comes from and what softens it
The mechanics of SE tax: the 92.35% multiplier, the Social Security wage base, the half-deduction, the extra 0.9% — and why the sticker rate overstates it.
The 1099 deductions checklist — what actually reduces your tax
Every major Schedule C deduction category with the real rules: mileage, home office, health insurance, retirement, and the write-offs that don’t exist.
The underpayment penalty, explained — what missing a quarter actually costs
How the estimated-tax penalty really works: daily interest per quarter, Form 2210, the annualized-income escape hatch, and the retroactive withholding fix.