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 Rightsizing for Retirement What does your home really cost? Estimate Your Health Care Costs in Retirement Studies show that health care concerns are the top of the list for Americans planning their retirements. How Much Home Can I Afford? With a few simple inputs you can estimate how much of a mortgage you may be able to obtain.