Planning for Retirement. Even once you've stopped working, you might still need to file a tax return and pay income tax -- and shockingly, you might also have to include some of your Social Security benefits as taxable income on your return. Yet those benefits come at a cost, and working Americans pay taxes out of their paychecks year in and year out to go toward paying current recipients of the program. Here's what you need to know:. New Ventures. What if I'm an Employee and Also Self-employed? Payroll Tax Documentation. Even though the payroll tax rate has stayed the same, the Social Security Administration typically boosts the amount of earnings that's subject to the tax. Moreover, about , self-employed workers earned at least the maximum earnings subject to Social Security payroll tax in the most recent year for which data's available. There's no wage base limit for Medicare tax.

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