Funny Fails and How Not to Be One of Them 

Let’s talk payroll—because if you think it’s as easy as writing a check and calling it a day, you may also believe unicorns do your taxes.

Payroll mistakes are some of the most common (and hilarious, if you’re not on the receiving end). Like the guy who accidentally paid himself twice and then asked HR if it was a “sign.” Or the small business that withheld zero taxes and thought the IRS wouldn’t notice. Spoiler: they noticed.

Top payroll mistakes that’ll bite you:

• Misclassifying employees vs. contractors (Hint: if they show up to your meetings every day, they’re probably not a freelancer).

• Forgetting to file IRS Form 941 quarterly (cue panic googling).

• Not tracking PTO or overtime properly. Suddenly Karen from HR has 96 unused vacation days.

How to avoid becoming a payroll horror story:

• Use a trusted payroll platform (Gusto, ADP, or QuickBooks Payroll)

• Know your federal and state tax deadlines

• Work with a bookkeeper who triple-checks your withholdings

Also, remember that payroll taxes are not your money. They are the government’s money, and they want it now (or with penalties later).

✅ Funny Tip: If your payroll process involves sticky notes and good intentions, it’s time to upgrade.