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 Retirement Questions That Have Nothing to Do With Money Things to consider before retirement. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP. Tax Freedom Day Assess how many days you'll work to pay your federal tax liability.