The Safe Harbor Rule: Self-Employed Penalty Protection
The safe harbor rule protects self-employed workers from IRS underpayment penalties. Here's exactly how it works and how to use it to your advantage.
Category Self-Employed
Read MoreThe Safe Harbor Rule: Self-Employed Penalty Protection
How to Open a SEP-IRA and Cut Your Tax Bill This Year
A SEP-IRA lets self-employed workers contribute up to 25% of net income—and deduct every dollar. Here's how to open one and maximize your 2025 contribution.
What Self-Employed Workers Need to Know About the 1099
Got a 1099-NEC or 1099-K this year? Here's what those forms mean, what income you must report, and how to handle taxes on every dollar you earned.
How to Avoid IRS Penalties as a Self-Employed Worker
Underpayment penalties can sneak up on self-employed workers. Learn the IRS safe harbor rules and how to make sure your quarterly payments are enough.
Freelance Income Tracker: Stay Organized for Tax Season
Tracking freelance income consistently is the key to stress-free tax season. Here's a simple system to log income, categorize expenses, and stay ready.
Bookkeeping Basics for Self-Employed Workers at Tax Time
Good bookkeeping makes tax season easy. These simple habits for tracking income and expenses will save you hours—and dollars—when you file.
How to Deduct Health Insurance as a Self-Employed Worker
Self-employed? You may be able to deduct 100% of your health insurance premiums. Here's exactly how the deduction works and how to claim it.
Q4 Estimated Taxes: What You Owe by January 15
Q4 estimated taxes are due January 15. This guide shows how to calculate your final quarterly payment and wrap up the tax year cleanly.
Gig Workers: Complete Tax Guide for Uber, DoorDash & More
Driving for Uber or delivering for DoorDash? You're self-employed in the IRS's eyes. This guide covers every tax obligation gig workers face.