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 Question Thank you! Oops! Related Content How Women Can Prepare For Retirement Are women prepared for a 20-year retirement? How Will Working Affect Social Security Benefits? Knowing the rules may help you decide when to start benefits. Whole Life: The Key to Unlocking your Retirement Imagine a retirement without having to worry about money? Well, it’s possible.