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? Address Thank you! Oops! Related Contents Retirement Redefined Around the country, attitudes about retirement are shifting. Three Key Questions to Answer Before Taking Social Security When to start? Should I continue to work? How can I maximize my benefit? My Retirement Savings Estimate how long your retirement savings may last using various monthly cash flow rates.