What you owe when nobody withholds it for you. Self-employment tax, quarterly payments, 1099 forms, deductions, and the deadlines that matter.
If you have a job alongside your freelance work, you can cover the tax on the freelance income by raising the withholding on the job instead of sending quarterly payments. That much is widely known. What is not widely known is that the two methods are not treated the same way in time — and…
One of you has a W-2. The other has 1099s, or a Stripe balance, or nothing that reports itself at all. You file one joint return, so there is one tax bill — and almost everything people get wrong here comes from forgetting that. The safe harbour is measured against the tax on the joint…
The W-9 came back with the LLC box ticked, and now you are not sure whether you owe this person a 1099. The answer is not “no” — it depends on a letter written next to that box, and half the time the letter is missing. Here is how to read the form you already…
A 1099-NEC arrived with the wrong number on it. You emailed the client. They said no, or they stopped replying, or the company no longer exists. Every article you have read assumes they cooperate. This one is about the other path — what you actually file, how to document it so the mismatch does not…
You file one return, not two. The job and the freelance work both land on the same Form 1040 — but they arrive by different routes, and only one of them had tax taken out along the way. That difference is why the refund you are used to can turn into a bill in the…
You do not file one state return for the year. You file two — one for each state, each covering the part of the year you lived there. Most people discover this in April, after they have already sent a year of estimated payments to the wrong place. Here is how the split actually works…
The 2026 rate changed in the middle of the year. Most mileage calculators still multiply everything by one number, which either costs you money or puts a wrong figure on your return. This one splits the year where the IRS split it. Below: why the split exists, which miles count, and the one decision you…
There is a published rule that says some first-year freelancers owe no estimated tax at all, whatever they earn. It is one sentence in Form 1040-ES, it is not conditional on income, and almost nobody mentions it. This is how to work out whether it applies to you, and what to do if it does…
Most of what you read about year-end tax moves is written for people with employers. For a freelancer the list is shorter than it looks — and one item on it is invisible, cannot be fixed in April, and costs more than everything else combined. This is what actually expires on December 31, 2026, and…
Your health insurance premiums are deductible, but not all of them, and not always. Two limits decide how much — one tied to what the business earned, one tied to whether a job was available to you. This calculator applies both. Everything below explains the two limits, and what happens to the part you cannot…