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 Retirement Questions That Have Nothing to Do With Money Things to consider before retirement. When to Self-Insure Choosing to bear the financial burden of an adverse event is called self-insuring. Do you know what that entails? Does Your Child Need to File an Income Tax Return? When your child has income, there’s a good chance that he or she will need to report it and pay taxes.