Timing Your Retirement This short video illustrates why knowing when to retire can be a crucial part of your strategy. Share | Have A Question About This Topic? Name Email Address Message Thank you! Oops! Related Content Does Your Portfolio Fit Your Retirement Lifestyle? Lifestyle considerations in creating your retirement portfolio. 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. Medicare Advantage 101 Overview of Medicare Advantage, what’s in them, special rules, and more.