Free Agent FinanceCategory
Taxes for freelancers and the self-employed
No employer is withholding anything for you — which means the tax system that felt automatic on a W-2 becomes something you have to run yourself, four times a year. Here's how.
When you're self-employed, you're responsible for two things an employer usually handles quietly in the background: paying income tax throughout the year instead of at one deadline, and covering both halves of Social Security and Medicare tax yourself — the full 15.3% self-employment tax, not just the 7.65% an employee sees on a pay stub.
That combination is why freelancer tax questions cluster around a few themes: how much to set aside, when payments are due, which expenses actually reduce the bill, and what happens if a payment is missed. The guides below walk through each of those in order, starting with the one question almost every new freelancer searches first.
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Taxes guides
Quarterly Estimated Taxes for Freelancers: The Complete Guide
How to calculate, schedule, and pay quarterly estimated taxes without penalties.
The Freelancer Tax Deduction Checklist: 25 Write-Offs
Every legitimate deduction self-employed workers overlook, organized by category.
How Much to Save for Taxes as a 1099 Contractor
A simple percentage method plus a free calculator to find your number.
Self-Employment Tax Explained: The 15.3% Broken Down
Where the rate comes from and how it's calculated.
1099 vs W-2: What Changes for Your Taxes
Withholding, tax rates, and deductions compared.
Home Office Deduction: Simplified vs Actual Expense
Which calculation method saves you more.
Sales Tax for Freelancers and Digital Services
Whether you need to charge sales tax, and when.
What Happens If You Miss a Quarterly Payment
How the penalty works, and how to fix it fast.
Self-Employed Tax Forms Checklist
Schedule C, SE, 1040, and more, explained.
State Taxes for Remote Freelancers
Residency, nexus, and double-taxation credits.
How to File a Tax Extension
What Form 4868 actually extends.
Freelancer Tax Deadlines Calendar
Every date that matters, in one place.
Deducting Health Insurance Premiums
Who qualifies, and how much.
1099-NEC vs 1099-K
What each form means for your return.
Estimated Tax Safe Harbor Rule
Avoid a penalty even if you owe more later.
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