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Maximizing Business Transportation Expense Deductions The costs of commuting from a personal residence to places of business or employment generally are nondeductible personal expenditures. The deduction for commuting costs is disallowed regardless of the distance involved.   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.