What Money to Take First? When you retire, deciding which money to use first can be critical to your long-term financial outlook. Share | Have A Question About This Topic? Name Email Address Message Thank you! Oops! Related Content Retirement Redefined Around the country, attitudes about retirement are shifting. 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.