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 Dreaming Up an Active Retirement When you retire, how will you treat your next chapter? How Will Working Affect Social Security Benefits? Knowing the rules may help you decide when to start benefits. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.