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 Contents A Fruitful Retirement: Social Security Benefit Taking your Social Security benefits at the right time may help maximize your benefit. When Should You Take Social Security Monthly Social Security payments differ substantially depending on when you start receiving benefits. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.