Oh boy, the weekend is here and Monday is quickly approaching...to pay quarterly payroll taxes. There's nothing quite like going from being a W-2 employee for so many years to being a small business owner. It's like taking the red pill when you do your taxes. I wish everyone had to experience writing a check to the IRS, State, and DES for unemployment taxes. I've been doing this for a while now, but I still have the same, sickening reaction every quarter. You W-2 employees see the deductions from your check, but it's not nearly as painful as actually having that money and then writing multiple checks to pay your taxes - trust me.