08/27/2026
Payroll is where I get the most "wait, am I doing this wrong?" questions. So let's clear a few up.
Should I be an S-corp? Sometimes. Past a certain point, and not a day before. It's a math problem with your actual numbers in it, not a rule of thumb from a networking event. If your profit's high enough, it can save real money; below that line, the costs eat the savings.
How often should payroll run? Whatever's consistent and legal in your state. Usually biweekly or semi-monthly. Pick one and hold it. Payroll chaos is just future-you's problem in disguise.
W-2 or 1099? You don't get to choose based on what's easier. The IRS decides it by how the work actually happens - who controls it, whose tools, whose clients. Guess wrong and the back taxes and penalties are yours.
Can I pay myself once a month? If you're an S-corp, you're on payroll and it has to be reasonable and regular. So yes, monthly can work, as long as it's actually running. If you're a sole prop or LLC, "paying yourself" is just a draw, not payroll, and the rules are different.
Payroll's one of those things that's boring right up until it's expensive. Got a question I didn't cover? Drop it below. 👇
