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 Retirement Plan Detectives A couple become Retirement Plan Detectives, searching records from old employers. 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.