Roth Conversions – The Simply Retirement Podcast

7 Essential Strategies for Successful Investing for Retirement (Ep. 121)

By The Simply Retirement Podcast | September 9, 2026

Retirement investing can bring many questions, especially when your savings need to support your lifestyle for decades. How do you balance growth, income, taxes, and market uncertainty when planning for life after work?

In this episode, I share my recent webinar from the New York Public Library’s Investing A-Z program, in which I discuss seven essential strategies for investing in retirement. I explain how a financial plan should guide investment decisions, why inflation can affect long-term purchasing power, and how retirees can think differently about market risk. I also cover the role of stocks, dividend growth investing, tax planning strategies, Roth conversions, charitable giving, and important questions to consider when working with a financial advisor.

Throughout the presentation, I focus on creating a thoughtful approach to retirement investing that connects financial decisions with the lifestyle you want to support.

Key points:

How a financial plan can guide retirement investment decisions instead of focusing only on portfolio performance
Why inflation and rising costs can affect retirement income needs over several decades of life
How retirees can measure investment risk by considering years of income during market downturns
The role of stocks, dividend growth investing, and long-term thinking in retirement portfolios
How tax strategies, Roth conversions, and charitable giving may influence retirement planning decisions
And more!

Resources:

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Retirement Tax Cliffs: The Hidden Costs Every Woman Should Understand (Ep. 112)

By The Simply Retirement Podcast | July 8, 2026

Retirement taxes aren’t always as straightforward as they seem. A decision that looks harmless today could create unexpected tax consequences, higher Medicare premiums, or reduced flexibility later.

How do income sources, tax brackets, Social Security, and healthcare costs all work together in retirement? What happens when a major life event changes your filing status and reshapes your financial picture?

In this episode, I discuss several retirement tax cliffs that can quietly affect retirement income planning, especially for women who are widowed, divorced, or managing finances independently. I explain how required minimum distributions, Social Security taxation, Medicare IRMAA surcharges, and healthcare subsidies can interact in ways many retirees don’t anticipate. We also share planning considerations that may help create greater flexibility, reduce surprises, and improve long-term retirement income decisions.

Key takeaways:

How widowhood or divorce can trigger tax changes that affect income, Medicare costs, and planning flexibility
Why required minimum distributions may create ripple effects beyond simply increasing taxable income
How Social Security taxation can rise unexpectedly when additional retirement income enters the picture
Why Medicare IRMAA surcharges often surprise retirees years after a financial decision is made
Ways proactive tax planning may help create flexibility and reduce unintended retirement expenses
And more!

Resources:

Connect with Eric Blake:

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Required Minimum Distributions (RMD) Explained: Risks, Timing, and Tax Planning Strategies (Ep. 92)

By The Simply Retirement Podcast | February 18, 2026

RMDs are one of those retirement rules that feel simple on the surface, until the tax consequences show up years later.

In this episode, I walk through what required minimum distributions are, when they start, and why missing or mismanaging them can quietly raise taxes, Medicare costs, and long-term financial stress. I explain how planning early creates flexibility, especially for women navigating retirement transitions, widowhood, or income changes. We also cover practical strategies that can help reduce the tax impact without turning retirement upside down.

Key takeaways:

How required minimum distributions work and when they begin under current law
The penalties and long-term damage caused by missed or unplanned RMDs
How RMDs can increase taxes on Social Security and Medicare premiums
Using qualified charitable distributions to reduce taxable income
Timing strategies like Roth conversions and filling lower tax brackets
And more!

Resources:

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This information is for educational purposes only and does not constitute tax advice. Converting to a Roth IRA is a taxable event and may increase your current-year tax liability. Roth conversions cannot be undone. Individuals should consult a qualified tax professional regarding their specific circumstances.

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How Social Security Gets Taxed: What You Need to Know (Ep. 54)

By The Simply Retirement Podcast | May 28, 2025

Most people think Social Security is straightforward—until taxes show up.

The truth is, what you don’t know about how your benefits are taxed can cost you more than you expect.

In this episode, I explain how Social Security gets taxed and why it hits harder for women filing single later in life. I break down the tax torpedo, walk through real examples, and share strategies to help you keep more of your income in retirement.

Key points:

What provisional income is and how it determines whether Social Security benefits are taxable
How even tax-free income sources like municipal bonds can increase Social Security taxation
The “Social Security tax torpedo” and how small withdrawals can trigger significantly higher taxes
Why Roth IRAs and strategic withdrawal planning can reduce the overall tax impact
The importance of early preparation, especially for women who may file as single in later retirement
And more!

Resources:

Connect with Eric Blake:

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