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No matter how much money you make, if you work and are at full retirement age or older, you are eligible to keep all of your benefits.
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There isn't a single optimal time of year to file for benefits. You have until age 70 to file for Social Security payments, but you can start doing so at age 62 if you're eligible.
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According to a general rule of thumb, you will require roughly 15 times your estimated annual after-tax retirement expenses if you plan to retire at age 60.
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Next steps