Timing Your Retirement This short video illustrates why knowing when to retire can be a crucial part of your strategy. 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. Term vs. Permanent Life Insurance When considering life insurance, it's important to understand your options. Coaches Coaches have helped you your whole life, in ways big and small. We’d like to be one of them.