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 Content Retirement Redefined Around the country, attitudes about retirement are shifting. Social Security: The 64,000 Dollar Question One of the most common questions people ask about Social Security is when they should start taking benefits. My Retirement Savings Estimate how long your retirement savings may last using various monthly cash flow rates.