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 | Related Content Don't Buy The Hype There are a lot of misconceptions about Social Security. Here’s the truth about three of them. Social Security: The $64,000 Question One of the most common questions people ask about Social Security is when they should start taking benefits. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.