The library
Guides for people who pay their own taxes
1099 Forms & Reporting
Form 1099-K, 1099-NEC, wrong or missing forms, and income no one reported for you.
Form 1099-K for Gig Workers: Who Gets One, What It Shows, and What the IRS Does With It
Payment apps and card processors report what they pay you on Form 1099-K. Here is who has to send one, why the number looks too big, and how the IRS uses it.
Form 1099-NEC: What It Means When a Client Treats You as an Independent Contractor
A Form 1099-NEC tells the IRS a business paid you as a nonemployee. That one label decides who pays the Social Security and Medicare tax. Hint: you do.
How to Reconcile Your Form 1099-K With Schedule C So the IRS Computer Stays Quiet
The number on your 1099-K is almost never your profit. Here is how to get from that gross figure to an accurate Schedule C without triggering a mismatch letter.
No 1099, Still Taxable: Reporting Cash, App Payments and Small Jobs Nobody Reported
Cash jobs, small clients, foreign clients and payments in trade often arrive with no form. The IRS still counts them as income, and it has ways to find them.
Sold Your Own Stuff Online and Got a 1099-K? How to Keep It From Being Taxed as Business Income
Selling your old furniture at a loss is not income. Reselling for profit is. Here is how to report personal sales on a 1099-K and where the IRS draws the business line.
The 1099-NEC Threshold Jumped From $600 to $2,000. Here Is What Changed for Freelancers
Congress raised the Form 1099-NEC reporting threshold to $2,000 for payments made after 2025. Fewer forms will be mailed. Your tax bill did not shrink with them.
Wrong 1099? Missing 1099? What Freelancers and Gig Workers Should Do Before Filing
Payers make mistakes, and the IRS believes their forms until you give it a reason not to. Here is how to fix a wrong or missing 1099 without missing your own deadline.
Self-Employment Tax
How the 15.3% tax on your net earnings works, the wage base, and the Additional Medicare Tax.
How Self-Employment Tax Is Calculated, Step by Step, With 2025 and 2026 Numbers
Self-employment tax is the Social Security and Medicare tax you pay on your own business profit. Here is the actual math, with worked examples and the year-specific limits.
Married and Running a Side Business Together? The Qualified Joint Venture Election Explained
When spouses run a business together, the IRS may see a partnership that owes a Form 1065. The qualified joint venture election offers a simpler path, if you meet the rules.
The $400 Rule: When a Side Gig Means You Have to File a Return and Pay Self-Employment Tax
Plenty of people think a small side gig is too small to matter. Under IRC 6017, $400 of net self-employment earnings is enough to require a return.
The 0.9% Additional Medicare Tax on Self-Employment Income: Who Owes It and How to Plan for It
Successful freelancers and high-earning couples with side businesses can owe an extra 0.9% Medicare tax that nobody withholds. Here is how the threshold and the math work.
Estimated Payments
Quarterly deadlines, the underpayment penalty, and juggling a W-2 job with a side gig.
Quarterly Estimated Taxes for the Self-Employed: 2026 Deadlines, Safe Harbors and How Much to Pay
Nobody withholds tax from your 1099 income, so the IRS expects you to pay four times a year. Here are the 2026 dates, the safe harbor rules, and the easy ways to pay.
Uneven Gig Income and the Estimated Tax Penalty: How the Annualized Method Can Cut It
The IRS assumes you earn the same amount every month. Most gig workers do not. The annualized income installment method lets you prove it and shrink or erase the penalty.
W-2 Job Plus a Side Gig: How to Use Withholding Instead of Quarterly Estimated Payments
If you have a paycheck, you have a tool most full-time freelancers do not: withholding. Used right, it can replace estimated payments and fix a late start on the year.
Your First Year of 1099 Income: Why You Owe in April and How to Keep It From Happening Again
The first year of self-employment usually ends with a surprise tax bill. Here is why it happens, what the first-year rules forgive, and how to set up year two so it does not repeat.
Rideshare & Delivery
Uber, Lyft, DoorDash and Instacart drivers: mileage, logs, tips, and app income.
Delivery Driver Taxes for DoorDash, Instacart and Other Apps: Multi-App Income, Miles and Tips
Delivery drivers often work two or three apps at once. That is good for income and bad for records. Here is how to keep the taxes straight when the apps do not talk to each other.
Rideshare Driver Taxes: Uber and Lyft Income, Mileage Rates, Tips and What the IRS Checks
Rideshare drivers are small business owners with a car, a phone and an app. Here is how the income, the mileage, the tips and the self-employment tax actually work.
Standard Mileage Rate or Actual Car Expenses? How Self-Employed Drivers Should Choose
The car is the biggest deduction most gig workers have. The method you pick in the first year can limit your options for the life of the vehicle, so pick on purpose.
The "No Tax on Tips" Deduction for Self-Employed Gig Workers: Who Qualifies and the Fine Print
Tips are still income, but for 2025 through 2028 many gig workers can deduct them. The deduction has a list of eligible jobs, a cap, a phase-out, and paperwork rules that matter.
Audits & Records
What the IRS looks at when it audits a Schedule C, and the records that win the argument.
Recordkeeping for the Self-Employed: What the IRS Requires, What to Keep and for How Long
Good records are the difference between an audit that takes an afternoon and one that takes a year. Here is what the law requires and a system simple enough to actually use.
Schedule C Audits: What the IRS Actually Examines When It Audits a Self-Employed Return
A Schedule C audit is two audits in one: did you report all your income, and can you prove your expenses? The Internal Revenue Manual tells you how examiners test both.
The Bank Deposits Analysis: How the IRS Rebuilds a Self-Employed Person's Income From Bank Records
If your bank deposits are bigger than your reported income, the examiner will want to know why. Here is how the bank deposits method works and how to answer it.
What a Mileage Log Has to Show to Survive an IRS Audit
Vehicle deductions get a stricter proof rule than almost anything else on Schedule C. Here is exactly what the regulation asks for, and how to build a log that meets it.
Deductions & Worker Status
Hobby or business, home office, QBI, health insurance, and whether you were really a contractor.
Backup Withholding on 1099 Pay: Why a Client or App Took 24% and How to Make It Stop
Contractors normally get paid in full. If a client or app suddenly starts holding back 24%, it is almost always a taxpayer identification number problem, and it is fixable.
Direct Sellers and Home Party Reps: How IRC 3508 Makes You Self-Employed and What That Means at Tax Time
Direct sellers are treated as self-employed by statute, not by guesswork. Here is what that means for income, inventory, self-employment tax and the losses many sellers report.
Paid on a 1099 but Treated Like an Employee? Form SS-8, Form 8919 and Your Tax Options
Calling you a contractor does not make you one. If a business controlled how you worked, you may owe only the employee half of Social Security and Medicare tax.
Side Hustle or Hobby? How IRC Section 183 Decides Whether Your Losses Count
If your side gig keeps losing money, the IRS may call it a hobby. That label wipes out your deductions but not your income. Here is how the line is drawn and how to stay on the right side.
The 20% QBI Deduction for Freelancers and Gig Workers: How It Works After the 2025 Law Change
Most self-employed people with a profit qualify for the qualified business income deduction. It is now permanent, it has a new minimum, and it does not reduce self-employment tax.
The Home Office Deduction for Freelancers: The Exclusive Use Test and the Mistakes That Lose It
The home office deduction is real and it is legal. It is also easy to get wrong, and the most common mistake is not about square footage. It is about the word exclusive.
The Self-Employed Health Insurance Deduction: Who Qualifies, the Monthly Test and the Profit Limit
If you pay for your own health insurance and run a profitable business, you may deduct the premiums without itemizing. The catch is in the monthly eligibility test and the profit limit.
More IRS Topics
Shorter general articles about IRS collection and compliance.
- Offer in Compromise: The Real Guide to Settling for Less
- Currently Not Collectible: When the IRS Agrees to Back Off
- Penalty Abatement: Legally Removing IRS Penalties
- IRS Payment Plans: Which One Fits Your Situation
- The 10-Year Clock: How IRS Tax Debts Expire
- Your CDP Hearing Rights: Challenge IRS Collection
- Payroll Tax: The Most Dangerous IRS Debt
- Innocent Spouse Relief: Escape Your Ex's Tax Debt
- Revenue Officer at Your Door: The Survival Guide
- Can Bankruptcy Eliminate Tax Debt?
- IRS Notices Decoded: What Every Letter Means
- Self-Employed? Your IRS Risk Factors
- Crypto and the IRS: What You Need to Know
- Foreign Accounts: FBAR and FATCA Basics
- IRS and Your Passport: When Tax Debt Grounds You
- Avoiding Tax Resolution Scams