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 A Fruitful Retirement: Social Security Benefit Taking your Social Security benefits at the right time may help maximize your benefit. Social Security: What’s Changing in 2016? There have been a number of changes to Social Security that may affect you, especially if you are nearing retirement. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.