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 Message Thank you! Oops! Related Content A Fruitful Retirement: Social Security Benefit Taking your Social Security benefits at the right time may help maximize your benefit. 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. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.