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 Estimate Your Health Care Costs in Retirement Studies show that health care concerns are the top of the list for Americans planning their retirements. Principles of Preserving Wealth How federal estate taxes work, plus estate management documents and tactics. Consider Keeping Your Life Insurance When You Retire Reasons to retain your coverage into your retirement years.