retirement checklist

Retirement Planning Checklist: What to Do 5 Years Before Retiring

You’ve spent decades saving and working toward retirement, but the final five years before you stop working are the most important.
This is when your focus shifts from building wealth to preserving and distributing it wisely.

At Virgil Wealth, we help clients simplify this transition so they can step into retirement with confidence, clarity, and peace of mind.

  1. Estimate Your Retirement Expenses and Income

Your retirement plan starts with understanding what your lifestyle will actually cost and where your income will come from.

Steps to take:

  • Estimate monthly expenses, including healthcare, travel, housing, and hobbies.

  • Review projected income from Social Security, pensions, and investment accounts.

  • Identify any income gaps and plan how to fill them.

2. Plan Your Social Security and/or Pension Strategy

Timing is extremely important when it comes to Social Security and pension distributions.

Evaluate:

  • The best age to begin benefits; delaying until age 70 can significantly increase payments.

  • Spousal and survivor benefits if you’re married.

  • Coordination with other income sources to manage taxes.

3. Create a Tax-Efficient Withdrawal Plan

Without careful planning, taxes can erode your retirement income. We will help prevent that from happening!

Checklist:

  • Decide the order to draw from accounts (taxable → tax-deferred → tax-free).

  • Consider partial Roth conversions before RMDs (Required Minimum Distributions) begin.

  • Plan withdrawals to stay in lower tax brackets and manage Medicare surcharges.

4. Prepare for Healthcare and Long-Term Care Costs

Healthcare is one of the largest retirement expenses, and in our experience, often underestimated.

Steps:

  • Review Medicare options (Parts A, B, D, and supplemental plans).

  • Consider long-term care insurance or hybrid life/long-term care policies.

  • Build medical costs into your retirement budget.

5. Update Estate and Legacy Plans

Your estate plan ensures your wealth is transferred smoothly and according to your wishes.

Key items to review:

  • Create or update wills, trusts, and beneficiary designations.

  • Review powers of attorney and healthcare directives.

  • Discuss charitable giving (direct or through Donor-Advised Funds) or legacy goals.

6. Meet With a Fiduciary Financial Advisor

A trusted advisor can coordinate your investments, taxes, estate, and retirement income strategy, helping you avoid costly mistakes and optimize your retirement.

At Virgil Wealth, we specialize in guiding clients through the final stretch before retirement, ensuring every detail of your plan is aligned with your goals.

The five years before retirement are critical. By refining your plan now, you’ll be positioned to enjoy the freedom you’ve worked so hard to achieve. Schedule a free 15 minute consultation by clicking the button below.

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Virgil Wealth Advisory, LLC (“Virgil Wealth”) is a registered investment advisor offering advisory services in the States of New York and Ohio and in other jurisdictions where exempted.  Registration does not imply a certain level of skill or training. The presence of this website on the Internet shall not be directly or indirectly interpreted as a solicitation of investment advisory services to persons of another jurisdiction unless otherwise permitted by statute. Follow-up or individualized responses to consumers in a particular state by Virgil Wealth in the rendering of personalized investment advice for compensation shall not be made without our first complying with jurisdiction requirements or pursuant an applicable state exemption.

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