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 | Related Content Should You Tap Retirement Savings to Fund College? There are three things to consider before dipping into retirement savings to pay for college. Social Security: The Elephant in the Room Some people wonder if Social Security will remain financially sound enough to pay the benefits they are owed. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.