A Fruitful Retirement: Social Security Benefit Taking your Social Security benefits at the right time may help maximize your benefit. 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 $64,000 Question One of the most common questions people ask about Social Security is when they should start taking benefits. An Inside Look at Retirement Living A number of questions and concerns need to be addressed to help you better prepare for retirement living.