5 Smart Investing Strategies The slideshow presentation that you would like to view is too large for your current screen resolution. Click here to view to view the slideshow at full resolution. Launch Presentation » Share | Have A Question About This Topic? Name Email Address Question Thank you! Oops! Related Content Three Key Questions to Answer Before Taking Social Security When to start? Should I continue to work? How can I maximize my benefit? Annuity Comparison This calculator compares a hypothetical fixed annuity with an account where the interest is taxed each year. Social Security: The 64,000 Dollar Question One of the most common questions people ask about Social Security is when they should start taking benefits.