When you work as an employee, taxes are withheld from every paycheck. By the time April rolls around, you've already paid most of what you owe. Filing is just a matter of squaring up. When you run a business, nobody withholds anything. The IRS still expects to be paid throughout the year, but now it's your job to make that happen. That's where estimated tax payments come in. And for many business owners, this is where tax planning goes sideways. Who Needs to Make Estimated Ta