3 Financial Questions Every Retiree Should Ask

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G. DeWayne McAnally, CFP

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Retirees face unique challenges, such as managing fixed incomes, navigating healthcare costs, and ensuring their savings last for the long haul.


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Here are three questions every retiree should ask to set the stage for retirement. (Photo by Sean Gallup)

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Retirement marks an exciting new chapter in life , filled with possibilities for relaxation, exploration, and time with loved ones. But alongside these opportunities comes the need for careful financial planning. Retirees face unique challenges, such as managing fixed incomes, navigating healthcare costs, and ensuring their savings last for the long haul. Asking the right questions can set the stage for a secure and fulfilling retirement.

Here are three critical financial questions every retiree should ask to stay on track.

1. Do I Have a Sustainable Withdrawal Strategy?

A key challenge in retirement is balancing your need for income with the need to preserve your savings. Withdraw too much too quickly, and you risk running out of money; withdraw too conservatively, and you might not enjoy the lifestyle you’ve worked so hard to achieve.

To address this, retirees should develop a withdrawal strategy that aligns with their goals, life expectancy, and risk tolerance. Common approaches include:

  • The 4% Rule: A traditional guideline suggesting you withdraw 4% of your portfolio annually, adjusted for inflation.
  • Dynamic Withdrawals: Adjusting withdrawals based on market performance or personal circumstances.
  • Bucket Strategy: Dividing your savings into short-term, medium-term, and long-term buckets to manage risks and liquidity needs.

Consulting a financial advisor can help refine your approach and ensure your withdrawals keep pace with your needs while safeguarding your future.

2. How Will I Manage Healthcare Costs?

Healthcare is often one of the most significant and unpredictable expenses in retirement. Fidelity estimates that the average retired couple will need hundreds of thousands of dollars to cover medical expenses, excluding long-term care. Understanding and preparing for these costs is essential.

Start by assessing your coverage:

  • Medicare: Familiarize yourself with what Medicare covers and consider supplemental insurance (Medigap) or Medicare Advantage plans to fill in gaps.
  • Long-Term Care Insurance: Determine whether you need coverage for potential long-term care needs, such as in-home assistance or nursing facilities.
  • Health Savings Accounts (HSAs): If you have an HSA, plan how to use it wisely in retirement.

Additionally, consider setting aside a dedicated portion of your savings for medical expenses. This proactive approach can help mitigate the financial strain of unexpected healthcare needs.

3. Am I Maximizing My Income Sources?

Retirees often have multiple income streams, including Social Security, pensions, retirement accounts, and personal savings. Optimizing these sources is crucial to make the most of your resources.

Key considerations include:

  • Social Security Timing: Deciding when to start collecting benefits can have a significant impact on your lifetime income. Delaying benefits until age 70 can increase your monthly payout, but earlier withdrawals might make sense for those with immediate needs or shorter life expectancies.
  • Required Minimum Distributions (RMDs): Understand when you’ll need to start withdrawing from tax-advantaged accounts like 401(k)s or IRAs to avoid penalties.
  • Tax Efficiency: Strategize withdrawals to minimize taxes. For example, consider drawing from Roth accounts, which provide tax-free income, or coordinating withdrawals to stay within favorable tax brackets.

By thoughtfully managing income streams, you can reduce financial stress and maintain a steady cash flow throughout retirement.

Planning for Peace of Mind

Retirement can be one of the most rewarding phases of life, but it requires diligent financial planning to ensure it remains stress-free. Asking these three questions—about your withdrawal strategy, healthcare costs, and income sources—can help you make informed decisions and protect your financial well-being.

With the right plan in place, you’ll be well-positioned to enjoy a secure and fulfilling retirement.

By Andrew Rosen, Contributor

© 2025 Forbes Media LLC. All Rights Reserved

This Forbes article was legally licensed through AdvisorStream.

G. DeWayne McAnally profile photo

G. DeWayne McAnally, CFP

President
G DeWayne McAnally, LLC
Office : 4057281649
Schedule a meeting