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. When Should You Take Social Security Monthly Social Security payments differ substantially depending on when you start receiving 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.