This year, as you wallow in anxiety waiting for the tax team to get back to you, I have a fun project for you. Make sure your state payroll tax settings are correct. This is the only time when it DOESN’T feel irrelevant and boring. So Take advantage of it.

If you work remotely for a company based in New York but you live and work outside of New York, then you pay taxes as if you're a New Yorker.

How does this even slip through? For THREE YEARS? Part of it had to do with a quirk of how taxes work in reciprocity states like Wisconsin. Part of it was because state agencies don’t talk to each other. And implementation teams aren’t tax experts. And some payroll providers don’t have enough error flags for situations like this. And humans are flawed. They make mistakes.

Your dark and mysterious payroll past comes back into your life. Another notice. Something unreadable. You thought you'd left this all behind. But here it is again. Your pulse quickens. You're back under the tax agency's smoldering gaze. And this time, they won't take no for an answer.

When you move, the old taxes need to be discontinued and the new ones added. This is true, even if your office stays in the same place. Or if you work from home. Especially if you work from home. If you don’t fix it soon, the state is going to send you a whopper of a bill when you file your tax return.

Many midwestern states have reciprocity agreements where each state agrees to let the other handle payroll taxes. Without keeping score. It’s the state tax equivalent of saying, “It’s cool, bro. I know you’ll get me next time.”

Here's a rule of thumb: The best states to work in are some of the worst states to work with.

Except that something didn’t add up. They didn’t even have employees for half that time, and one of the people they were assessing violations on wasn’t even in the state.

Letters from government agencies can be real scary sometimes. Especially when they contain words like "Warrant" and penalties with commas in them. By all means, take these letters seriously. But don't let them scare you.

But what passes for “security” in these agencies is a cruel joke. It is no more realistic for you to expect me to tap Mr. or Ms. Business Owner on the shoulder and hand them the phone than it is for me to demand that you tap the governor on the shoulder and get him/her on the phone.

But why would someone take a 40+% pay cut by choice? That time must be more valuable than money. There are plenty of reasons besides laziness why this might be true.

Did you know: Payroll doesn’t update tax settings automatically when someone moves. If you live somewhere where it’s common to commute across state lines, having different settings for where someone lives and works seems natural.