Author: Sammy Eom

Sammy Eom builds financial software for freelancers. She writes The Owner's Handbook to cover what you actually need to know to run your own thing: pricing, invoicing, taxes, business structure, and the tools behind them.
  • How to Prove Freelance Income to a Landlord

    The number a landlord ends up judging you on is line 31 of your Schedule C — net profit — not the money your clients actually sent you. On a $96,000 year with $31,000 of deductions, the figure that gets measured against the rent is $65,000. Everything else about proving freelance income follows from that…

  • Estimated Taxes When One Spouse Is Self-Employed

    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…

  • Do You Send a 1099 to an LLC? Read the Letter on the W-9

    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…

  • Your 1099 Is Wrong and the Client Will Not Fix It

    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…

  • S Corp and You Never Ran Payroll: What Happens Now

    You elected S corporation status, took money out of the business all year, and never ran a payroll. Nothing has gone wrong yet — nobody has sent you anything. But the return that reports the year is due in March, and what you put on it decides how this ends. Here is what the rule…

  • W-2 Job and 1099 Income in the Same Year: How to File

    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 Moved States Mid-Year. Now You File Two State Returns.

    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…

  • Mileage Deduction Calculator for 2026 (Both Rates)

    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…

  • Do You Have to Pay Quarterly Taxes in Your First Year of Freelancing?

    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…

  • Invoice Late Fee Calculator: Four Ways to Count the Same Clause

    Most late fee calculators give you one number. The problem is that the clause on your invoice supports four, and the gap between them on a $4,000 invoice is thirty-five percent. This one shows all four, so you can see which reading your contract is actually claiming. Below: where the four numbers come from, and…