Retirement Buying a Vacation Home? 5 Questions to Consider First Share | Related Content 4 Things to Consider While You’re Planning When to Retire As the decision to retire approaches, you’ll find the choice of when to retire is rarely black and white. You Would Rather Be... Are you a thrill seeker, or content to relax in the backyard? Use this flowchart to find out more about your risk tolerance. What Do Your Taxes Pay For? Here's a breakdown of how the federal government spends your tax money.