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. Have A Question About This Topic? Name Email Address Message Thank you! Oops! Related Content Contributing to an IRA? Determine if you are eligible to contribute to a traditional or Roth IRA. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP. Three Key Questions to Answer Before Taking Social Security When to start? Should I continue to work? How can I maximize my benefit?