Whether or not your benefits will increase depends on how much money you earn and how many years of earnings records you have. If you have fewer than 35 years of earnings, additional work years will certainly raise your benefit amount. Similarly, if you are currently earning a significantly higher amount than you have earned in the past, this will also increase your benefit amount. When performing your retirement planning, you should likely seek the help of a financial advisor or personal finance expert. You should also consider any income from retirement accounts, like an IRA or 401k, in addition to your Social Security benefits.