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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.   Capital Gains and Losses Technically, almost everything you own and use for personal, pleasure, or investment purposes is a capital asset.