1099 & Self-Employment Tax Guides
Plain-language explainers on the rules behind the numbers — quarterly payments, deductions, and the safe-harbor rule — written to work alongside the calculator, not replace it.
How these guides fit together
Each guide explains one rule in depth — why it exists, how the IRS defines it, and what a real worked example looks like — while a dedicated calculator handles the arithmetic for your own numbers. Read the guide first if you want to understand why a number comes out the way it does; use the calculator directly if you just need the number.
Where to start
- Paying quarterly, or worried about a penalty? Start with the safe-harbor guide below, then use the quarterly tax calculator.
- Wondering why your deduction looks smaller than 20% of your profit? The QBI guide explains the taxable-income cap; the QBI calculator gives you your actual number.
- Working from home or driving for business? The home office & mileage guide covers both deductions, with dedicated home office and mileage calculators.
All guides
- Quarterly Estimated Taxes & the Safe Harbor Rule
How the safe-harbor rule works, and how to avoid an underpayment penalty.
- The QBI Deduction for Self-Employed Freelancers, Explained
What the 20% Qualified Business Income deduction is and how it lowers your tax bill.
- Home Office & Mileage Deductions for 1099 Freelancers
The two ways to deduct home-office costs and vehicle mileage.