Tax topics for the self-employed
Each guide walks through a single tax concept the way an experienced friend would explain it. No jargon, real examples, and links back to the calculators when you want to plug in your own numbers.
How Self-Employment Tax Actually Works — A Plain-English Guide for 2026
Why freelancers pay 15.3% instead of 7.65%, how the half-SE deduction softens the blow, and a worked example you can follow line by line.
Read the guide →The Top 1099 Deductions Most Freelancers Miss (and What They Cost You)
A field guide to the dozen Schedule C line items the average freelancer underclaims — with the real-dollar tax impact at common income levels.
Read the guide →Quarterly Estimated Taxes: The Complete 2026 Guide
When to pay, how much, the two safe harbors, the annualized income method, and how to send a payment without penalty.
Read the guide →Schedule C Walkthrough: Line by Line for First-Time 1099 Filers
Every line of Schedule C, what it captures, common mistakes, and a worked example of a freelance designer with $80k revenue.
Read the guide →The Home Office Deduction: Simplified Method vs Actual Expense
The deduction with the worst PR — when you qualify, how to choose between methods, and the depreciation-recapture trap homeowners should know about.
Read the guide →The Mileage Deduction: Standard Rate vs Actual Expense Method
The 70¢/mile shortcut versus actual-expense math, the lock-in rule that traps first-year filers, and what counts as a business mile.
Read the guide →Solo 401(k) vs SEP IRA: Which Saves a Self-Employed Person More
Side-by-side at three income levels: why Solo 401(k) almost always wins, when SEP IRA still makes sense, and the Roth wrinkle worth $1,000+/year.
Read the guide →The Self-Employed Health Insurance Deduction (Schedule 1, Line 17)
A $7,000+/year deduction most freelancers under-claim. Who qualifies, what counts, and the ACA premium tax credit interaction headache.
Read the guide →The S-Corp Election: When It is Worth Filing Form 2553
How the SE tax savings really work, the reasonable salary rule, the annual overhead, and a worked example showing $6k+/year in real savings.
Read the guide →The IRS Underpayment Penalty: How It Works and How to Avoid It
The interest charge most freelancers do not realize they owe — how it is calculated, the safe harbors that prevent it, and how to fix a missed quarter.
Read the guide →Taxes for Etsy, eBay, and Shopify Sellers in 2026
The 1099-K threshold, inventory and COGS, sales tax versus income tax, and the deductions specific to product sellers.
Read the guide →Taxes for Uber, Lyft, and DoorDash Drivers in 2026
The mileage deduction that changes everything, the P1/P2/P3 rule, platform-fee deductions, and a real worked example for a full-time driver.
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