Retirement Checklist: Five Years Before You Retire

A practical guide to preparing for retirement.

Questions? Call 360 Wealth Management • 918-209-5367

Complete this checklist during the five years leading up to retirement. Checking these items off before your last day of work can help reduce stress, minimize taxes, and improve your long-term financial outcomes.

• Estimate your retirement spending and determine how much monthly income you'll need.
• Build a comprehensive retirement plan that models different retirement dates and scenarios.
• Confirm when you can comfortably retire without running out of money.
• Decide when to begin Social Security after comparing multiple claiming strategies.
• Understand where your health insurance will come from before Medicare and after age 65.
• Review Medicare enrollment deadlines and avoid late-enrollment penalties.
• Create a lifetime tax strategy—not just this year's tax plan.
• Identify low-income years that may be good opportunities for Roth conversions.
• Estimate future Required Minimum Distributions (RMDs) and determine whether reducing them now makes sense.
• Determine which accounts you'll spend first (taxable, IRA, Roth, cash) rather than withdrawing randomly.
• Build a retirement income strategy that coordinates withdrawals with taxes.
• Review your investment allocation and make sure it matches your retirement income needs and risk tolerance.
• Create a cash reserve for unexpected expenses and market downturns.
• Review pensions, annuity options (if applicable), and survivor benefits before making irreversible elections.
• Update wills, trusts, powers of attorney, beneficiary designations, and healthcare directives.
• Discuss legacy goals and whether it makes sense to pay taxes today rather than leaving taxable IRAs to heirs.
• Estimate healthcare and long-term care costs as part of your retirement plan.
• Review insurance needs, including life, disability (if still working), umbrella, and long-term care coverage.
• Pay off or evaluate major debts such as mortgages before retirement if appropriate.
• Schedule a retirement readiness review 12–24 months before retiring.

360 Wealth Management
918-209-5367
Better financial decisions come from seeing the whole picture.