Tax clarity for the self-employed
Freelance income, minus the tax surprises.
If you're self-employed, nobody withholds tax for you — you owe the IRS four times a year, plus 15.3% in self-employment tax on top of income tax. These guides teach the actual rules with real 2026 numbers and worked examples, so quarterly taxes become a routine instead of a crisis.
2026 figures every 1099 earner should know
The problem, in three parts
Nobody withholds for you
Every 1099 dollar arrives with its taxes still attached. Without a system, that money feels like spending money — until April.
The IRS charges for lateness
Skip quarterly payments and you can owe an underpayment penalty on top of the tax itself — calculated per quarter, so catching up late doesn't erase it.
Guessing doesn't scale
SE tax, income tax, state tax, safe harbor, deductions — the math is straightforward but tedious. Most freelancers don't do it, and that's exactly the problem.
The guides
Estimated Taxes
Quarterly Estimated Taxes Explained: Who Has to Pay, the 2026 Deadlines, and How to Calculate What You Owe
Self-employed? You probably owe the IRS four times a year, not once. Here are the 2026 quarterly deadlines, who must pay estimated tax, how to calculate it, and what happens if you skip.
Read the guide →Self-Employment Tax
Self-Employment Tax: The 15.3% Every Freelancer Pays (and How It's Really Calculated)
Self-employment tax is 15.3% — but on 92.35% of your profit, with a wage base cap and an extra Medicare layer. Worked examples for 2026 show exactly how the math works.
Read the guide →1099 Basics
The 1099 Freelancer's Tax Guide: What's Taxable, 1099-NEC Basics, and Records That Keep You Safe
All your freelance income is taxable — 1099 or not. How 1099-NEC forms work, the $600 threshold, what counts as taxable income, and the records the IRS expects you to keep.
Read the guide →Deductions
Schedule C Deductions Freelancers Miss: Home Office, Mileage, Health Insurance, Retirement, and More
The most commonly missed freelance tax deductions — home office (simplified vs. actual), mileage at 2026 IRS rates, self-employed health insurance, retirement contributions, and the everyday categories that add up.
Read the guide →Safe Harbor
The Safe Harbor Rule: How to Legally Avoid Underpayment Penalties (With a Worked Example)
The safe harbor rule lets you avoid IRS underpayment penalties by paying 90% of this year's tax or 100%/110% of last year's. How it works, who qualifies, and a worked example.
Read the guide →Tax Reserve
How Much to Set Aside From Every Freelance Payment: Building Your Tax Reserve Rate
Stop guessing what to save for taxes. How to compute your personal reserve rate from your real numbers, separate tax money the day it lands, and run a quarterly rhythm that ends the April shock.
Read the guide →Learn the rules free. Automate the math for $39.
The guides teach you how quarterly taxes work. The Self-Employed Quarterly Tax Command Center does the work: a 13-tab workbook with live formulas for quarterly payments, tax reserve tracking, safe harbor targets, mileage and home office calculators, and a year-end CPA packet. Works in Google Sheets and Excel.
Get it on Gumroad — $39