How Do You Set Aside Estimated Tax Payments? More and more individuals are venturing outside the regular paychecks of a nine-to-five job and striking out on their own with side businesses, consulting, and self-employment—which means more people are paying estimated taxes throughout the year to keep up with Uncle Sam. When you're collecting payments from clients and customers and an employer isn't automatically deducting state and federal taxes, four times a year—on January, April, June, and September 15th (today)—you've got to pony up a portion of what you'll owe for the tax year. Since today is one of those four dreaded estimated tax days, we want to know: how are you freelancers and sole proprietors setting aside, tracking, and paying your estimated tax? Let us know in the comments. (Here's more on how to automate saving for estimated tax payments and the rest of your finances.)