Five Key Retirement Challenges (and Solutions), Ep #393

Mar 24, 2025

Preparing for retirement involves more than just saving money. This discussion highlights five critical challenges retirees face, including financial instability and skyrocketing healthcare costs. Practical solutions like flexible withdrawal plans and tax-efficient options, such as Roth conversions, are shared. The hosts also delve into estate planning essentials to safeguard loved ones. A listener asks about using a MIGA ladder strategy to enhance financial security, providing insights into annuities and their role in a retirement portfolio. Retire with confidence!

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ADVICE

Financial Instability

Structure a flexible withdrawal strategy and asset allocation.
Role-play your reactions to market downturns to avoid emotional decisions.

ADVICE

Healthcare Costs

Plan for healthcare costs beyond Medicare with HSAs and Medigap.
Consider your home equity as a potential resource for long-term care expenses.

ADVICE

Taxes in Retirement

Utilize Roth conversions and tax-efficient withdrawals to minimize taxes.
Be mindful of the impact of required minimum distributions (RMDs) on your tax liability.

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Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn’t just about having enough money—it’s about managing risks that can threaten your financial security and lifestyle.

In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger’s Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they’re not prepared.

We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones.

Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.

If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you're years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead.

Outline of This Episode

(0:00) 5 Key Retirement Challenges (and Solutions)
(1:17) Retirement headline: Kiplinger’s article on retirement challenges
(1:42) Challenge #1: Financial instability
(4:09) Challenge #2: Healthcare and long-term care costs
(6:33) Challenge #3: Taxes in retirement
(7:33) Challenge #4: Inflation’s impact on retirement income
(8:32) Challenge #5: Estate planning oversights
(10:25) Listener question: MIGA ladder strategy for retirement income

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