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 Supplementing Retirement Income with Whole Life Whole Life insurance can add to your retirement income and allow you to live confidently. Problems with Probate Probate can be a completely public process, or it can be managed to include as little information as possible. Why Medicare Should Be Part of Your Retirement Strategy How Medicare can address health care needs in your retirement strategy.