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Retirement Readiness Checklist

Use this checklist to organize the key decisions that often matter most in the years leading up to retirement and in the first years after you stop working.

If you would prefer a printable version, you can also download the checklist as a PDF.

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Income Planning

  • List the income sources you expect to rely on in retirement.
  • Estimate when each source of income begins and how dependable it is.
  • Review how much you may need to withdraw from savings each year.
  • Think about whether your retirement spending will be level or change over time.

Taxes

  • Identify which accounts are taxable, tax-deferred, and tax-free.
  • Review whether withdrawal timing could affect your tax bracket.
  • Look at Roth conversion opportunities before required distributions begin.
  • Consider whether large one-time events could create avoidable tax surprises.

Social Security and Medicare

  • Compare filing ages and understand the tradeoffs of claiming early or waiting.
  • Review how your claiming decision may affect a spouse or surviving spouse.
  • Mark key Medicare enrollment windows and coverage decisions.
  • Think about how health care costs fit into your retirement budget.

Investments and Risk

  • Check whether your portfolio still matches your time horizon and withdrawal needs.
  • Review how much short-term cash or reserves you want available.
  • Consider whether you understand how market volatility could affect your plan.
  • Make sure your investment strategy supports income needs, not just long-term growth.

Estate and Organization

  • Review beneficiary designations on retirement accounts and insurance policies.
  • Confirm that wills, powers of attorney, and health care directives are current.
  • Organize account information, passwords, and important financial documents.
  • Make sure trusted family members know where essential documents can be found.