Retirement When Should You Take Social Security Monthly Social Security payments differ substantially depending on when you start receiving benefits. Thinking of Retiring Abroad? However exciting retiring abroad may sound, it deserves considerable planning. Your Changing Definition of Risk in Retirement A change in your mindset during retirement may drive changes to your portfolio. Social Security: The $64,000 Question One of the most common questions people ask about Social Security is when they should start taking benefits. 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. Do I have enough? Have a Question Name Email Address Phone Question Thank you! Oops!