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Tax Aspects of Becoming Self-employed Individual taxpayers are opting to start their own businesses for myriad reasons. Regardless of why you're contemplating self-employment, you should consider several basic tax-related issues before and immediately after actually leaving your current job.   Federal Taxation of Social Security Benefits With millions of baby boomers close to retirement age and job losses inflicting financial strain on additional millions, many taxpayers are looking to social security benefits for financial assistance.   Which Is Best for Your Business: Section 179 or 100% Bonus Depreciation? Taxpayers who acquire assets for use in their trade or business activity have a very good chance of writing off the entire cost, thanks to 100% bonus depreciation plus very generous Section 179 deduction limits.