How to Retire Early Retiring early sounds like a dream come true, but it’s important to take a look at the cold, hard facts. Share | Have A Question About This Topic? Name Email Address Question Thank you! Oops! Related Content How Will Working Affect Social Security Benefits? Knowing the rules may help you decide when to start benefits. Federal Income Tax Use this calculator to estimate your income tax liability along with average and marginal tax rates. Social Security: The 64,000 Dollar Question One of the most common questions people ask about Social Security is when they should start taking benefits.