If you’re filing your self-employed taxes for the first time, you’re likely wondering what exactly a tax deduction is. Here, we’ll walk you through the most common-and not so common-tax deductions for the self-employed, and guide you through the paperwork to help you file your taxes accurately. Whether you’re filing your business taxes as a self-employed worker for the first time or the 20th, there are certain best practices that can save you thousands of dollars a year. But, when you’re self-employed, the labyrinth of paperwork and potential tax deductions creates a tax situation that’s enough to give even the most laid-back freelancer heartburn. Filing your taxes as a W-2 employee can be overwhelming.