I recently helped with a migration off of a PEO. The client was frustrated with all the ways that the PEO was curtailing their decisions and all of the extra work it involved. “Extra work?” you ask. “But PEOs are supposed to save work.” That’s the myth.

Like you can just tap them on the shoulder and hand them the phone. “Excuse me, Mr. Zuckerberg. Can you please talk to this guy Doug in Minnesota?”

I can’t stand it when people insist on unnecessary steps. Especially if those unnecessary steps are self-defeating.

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.

Your registered agent is just someone in another location that is authorized to accept mail for you. That's 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.

Because some of a company's most sensitive and highly-regulated data flows through the HRIS, very few people get full insight into everything that’s happening in the platform. HR software is a pretty blind item. You don’t get to try before you buy. Even with the providers who give you a sandbox, it’s hard to get a true sense of performance until you have live data.

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.

Have you ever wondered what it would be like if you threw five cats in a bag and asked them to run your payroll? Or have you already tried Paylocity?

There’s more to the difference between an employee and a contractor than whether the company withholds taxes.

To get this one solved, I had to engage Claire-en mode. I demanded to speak to a manager. When the first person wouldn’t call a manager, I hung up and called again.

You know why their checks are cut by ADP? Because most of them work at big, old companies and switching payroll providers is really, really hard at that size. And because people don’t know any better.

The PEO issues the paycheck, but you pay the wages, taxes, and employer portion of benefits. Since the PEO is the employer on paper, they handle registering for state agencies and tracking compliance laws. And because PEOs can pool all of their client-employees, you get access the more affordable and flexible large-group benefits.

Justworks just works. Whether you’re reading that sentence positively or negatively, you’re right.

Here’s why your paycheck takes so long: Many companies pay in arrears. Which is a fancy way of saying that there’s a gap between the end of the pay period and when you actually get paid. If you’re paid hourly, there’s literally no way to get you paid without a gap. Here’s what’s happening in that time:

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.

I just really, really love Rippling. Because I’ve used it. And I’ve used its competitors. And, in my opinion, Rippling is better. At (just about) everything.

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.

Hey, Tyler. I noticed you have seven dependents on your tax form. Usually those would be people in your immediate family who share your living expenses and rely on your income, like a spouse and kids. Are you sure that all of these people would actually be considered dependents for tax purposes?

For my small business clients (who aren’t considering a PEO), the decision often comes down to Bamboo or Gusto. Both Bamboo and Gusto have clean, easy-to-understand user interfaces with cute graphics that really do make dry and stressful processes less intimidating and occasionally “delightful.”