Retirement Planning – The Simply Retirement Podcast

Beneficiary Designations: 9 Key Questions for Retirement Planning (Ep. 122)

By The Simply Retirement Podcast | September 16, 2026

Life changes, but the beneficiary forms attached to your retirement accounts, insurance policies, and other assets may still reflect decisions you made years ago.

In this episode, I explain why beneficiary reviews should be part of ongoing retirement planning and walk through nine questions that can help you determine whether your current designations still reflect your wishes. I cover primary and contingent beneficiaries, coordinating designations with your estate plan, trusts, minor beneficiaries, charitable giving, inherited IRA rules, and potential tax consequences.

I also share real client situations that show why verifying these details can be so important after divorce, widowhood, and other major life changes.

Key points:

Why beneficiary forms should be reviewed after divorce, widowhood, remarriage, and other major life changes
How beneficiary designations can control where certain assets go, regardless of instructions written in your will
Why primary and contingent beneficiaries should be checked across IRAs, 401(k)s, insurance, and other accounts
How trusts, minor beneficiaries, charitable gifts, and inherited retirement accounts can require added planning
How beneficiary choices can affect taxes, distribution options, and what your family ultimately receives
And more!

Resources:

Connect with Eric Blake:

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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:

Connect with Eric Blake:

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Social Security Headlines: What They Really Mean for Your Retirement (Ep. 120)

By The Simply Retirement Podcast | September 2, 2026

For women approaching or already in retirement, Social Security decisions can feel harder when tax questions, funding projections, and proposed legislation all appear in the headlines at once.

How do you separate information that affects your plan from news that simply deserves your attention?

In this episode, I answer a listener’s question about Social Security tax withholding while working at age 70. I explain what it really means when up to 85% of Social Security may be taxable, how withholding choices work, and why your broader tax picture matters. I also break down the 2026 Social Security Trustees Report, what the projected funding shortfall actually means for benefits, and what the proposed PROMISE Act could change. Most importantly, I explain why retirement decisions should be based on your circumstances and current law rather than headlines or predictions.

Key points:

Why delaying Social Security until age 70 can increase monthly income for life and potentially affect survivor benefits
What “85% of Social Security is taxable” actually means and how provisional income affects federal taxation
How the five Social Security withholding options differ and why your full income picture should guide the choice
What the 2026 Trustees Report says about future benefits and why a funding shortfall doesn’t mean benefits disappear
How to think about the proposed PROMISE Act without changing your retirement plan based on legislation that isn’t law
And more!

Resources:

Connect with Eric Blake:

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How to Decide If an Annuity Fits Your Retirement Plan (Ep. 119 | Pt. 4)

By The Simply Retirement Podcast | August 26, 2026

If you’re a woman planning for retirement and an annuity has been recommended to you, the hardest part may not be understanding how it works. It may be deciding whether it actually belongs in your retirement plan.

Asking better questions can help you understand what you’re considering before you commit.

In this episode, I explain how to evaluate whether an annuity fits within your retirement plan. I walk through the questions I want you to ask about the retirement need you’re trying to address, other available options, what an annuity actually provides, what you may give up in return, how fees and surrender charges work, and what could happen if your circumstances change. I also explain why reviewing the contract and understanding your free look period can give you time to make a more informed decision.

Key points:

Start by identifying the retirement need you want an annuity to address before evaluating the product itself.
Compare an annuity with other ways of accomplishing the same retirement goal before making your decision.
Understand exactly what the contract protects or provides, including income, principal, and access to money.
Review rider fees, commissions, advisory fees, and surrender charges so you know what you’re paying for.
Consider how changing health, family needs, or cash needs could affect whether the annuity still fits your plan.
And more!

Resources:

Connect with Eric Blake:

Annuities are insurance products issued by insurance companies and involve costs, fees, limitations, and contractual terms that vary by product. Guarantees are backed solely by the claims-paying ability of the issuing insurance company. Before purchasing an annuity, investors should carefully consider their financial objectives, risks, charges, expenses, and contract features, and consult with their financial, tax, and legal professionals.

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How Are Annuities Taxed? A Simple Guide for Retirement (Ep. 118 | Pt. 3)

By The Simply Retirement Podcast | August 19, 2026

Retirement tax planning can feel confusing, especially when annuities enter the conversation.

I’ve found that many people aren’t really asking about the annuity itself. They’re trying to understand what happens to their money, how it’s taxed, and whether an annuity is the right fit for their retirement.

In this episode, I continue our annuity series by walking through the tax rules that often create the most confusion. I explain why the source of your money matters, how qualified and non-qualified annuities are taxed differently, and why buying an annuity inside an IRA doesn’t change the tax treatment of that retirement account.

We also discuss how withdrawals work, how tax deferral fits into retirement planning, and why every annuity decision should begin with one simple question: What do I want this money to do for me?

Key takeaways:

Understanding how the source of your money determines the way an annuity is generally taxed
Why placing an annuity inside an IRA usually doesn’t change the retirement account’s tax rules
The difference between qualified and non-qualified annuities when withdrawals begin
How tax deferral allows earnings to continue growing until money is withdrawn
Asking what role an annuity should play before deciding whether it belongs in your retirement plan
And more!

Resources:

Connect with Eric Blake:

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Don’t Wait for a Crisis: How to Talk With Aging Parents (Ep. 117)

By The Simply Retirement Podcast | August 12, 2026

We’ve learned that many of the most important retirement decisions aren’t only about finances. They’re about family, communication, and preparing for moments that none of us hope will come.

In this episode, I speak with Tami Calais, Aging and Change Coach, owner of Calais Senior Consult, and Motivational Interviewing Practitioner, about why families often delay difficult conversations with aging parents until a crisis leaves them with few choices. We discuss how adult children can approach these discussions with empathy instead of urgency, why connection creates better outcomes than control, how having conversations earlier can help families avoid unnecessary guilt, and practical ways families can preserve a loved one’s voice while planning for future care.

Key takeaways:

Why waiting for a health emergency often makes family decisions much more difficult and emotional
How empathy creates safer conversations than immediately offering advice or solutions
Ways adult children can support aging parents while respecting their independence and choices
Why preserving an older adult’s voice should remain the priority throughout every planning discussion
Practical communication techniques that help families prepare before difficult care decisions arise
And more!

Resources:

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Connect with Tami Calais:

About our Guest:

Tami Calais is the Aging & Change Coach — a speaker and Motivational Interviewing practitioner who helps families and senior living organizations navigate the hardest conversations about aging with confidence instead of avoidance. With 15+ years in senior living and a methodology built on curiosity over control, Tami teaches a different way to talk about change: one rooted in connection, not confrontation. She is the founder of Hard Conversations, Handled Well, and her work is grounded in a simple belief — resistance isn’t a personality trait; it’s the physics of communication.

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Which Type of Annuity Fits Your Retirement Plan? (Ep. 116 | Pt. 2)

By The Simply Retirement Podcast | August 5, 2026

When people hear the word annuity, they often picture a stream of retirement income. While that’s certainly part of the story, there are important decisions that come long before those payments ever begin.

How do the different types of annuities work? Which one might fit your retirement goals? And what questions should you answer before comparing products?

In this episode, I continue our annuity series by explaining the different types of annuities and how each one is designed to solve a different retirement planning challenge. I clarify the difference between an annuity as a financial concept and an annuity as a financial product, explain how immediate, deferred, fixed, fixed indexed, and variable annuities work, and return to one guiding question that can bring greater clarity to every retirement decision: What are you trying to accomplish?

Key takeaways

How viewing annuities as financial products changes the decisions involved before purchasing one
Why immediate and deferred income annuities serve different retirement income objectives
How fixed indexed annuities balance market participation with protection from direct market losses
Why variable annuities may appeal to investors seeking tax-deferred growth opportunities
How identifying your retirement goal first helps narrow the annuity choices that may fit your plan
And more!

Resources:

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Understanding Annuities Before You Decide if They Belong in Your Retirement Plan (Ep. 115 | Pt. 1)

By The Simply Retirement Podcast | July 29, 2026

Annuities often become part of the retirement conversation during major life changes, yet many people still aren’t sure what they actually are or when they make sense.

In this episode, I begin a four-part series designed to help you understand annuities before you ever evaluate a specific product. We discuss what an annuity actually is, why insurance companies created them, how they can provide retirement income, and why every decision should begin with your retirement goals rather than product features.

We also explore accumulation versus income phases, tax deferral, and the questions you should ask before deciding whether an annuity belongs in your retirement plan.

Key takeaways:

How annuities work as insurance contracts that may provide retirement income now or later
Why retirement planning should begin with your goals before discussing financial products
How accumulation and income phases affect the way annuities function over time
Why tax deferral should be viewed as one feature rather than the primary reason to buy
Questions that help determine whether an annuity belongs in your retirement strategy
And more!

Resources:

Connect with Eric Blake:

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Helping Women Make Better Retirement Decisions After Life Changes (Ep. 114)

By The Simply Retirement Podcast | July 22, 2026

Retirement decisions often happen during life’s most emotional moments. When you’re grieving, retiring, or suddenly making financial choices on your own, how do you know you’re asking the right questions or talking to the right people?

In this episode, I share a story from a recent anniversary trip that reminded me why retirement planning is about much more than investments.

Through conversations with women facing divorce, widowhood, and retirement, I explain how decisions around Social Security, beneficiary designations, retirement accounts, taxes, and financial guidance are often connected in ways people don’t realize. We also talk about why every financial advisor approaches retirement differently, why asking the right questions matters, and how finding guidance that fits your situation can influence retirement for years to come.

Key takeaways:

Why retirement decisions made after losing a spouse deserve thoughtful guidance before taking action
How Social Security timing can affect lifetime retirement income and future financial flexibility
Why beneficiary designations and retirement accounts often create unexpected challenges for widows
How communication between financial and tax professionals can improve retirement decisions
Questions women should ask before choosing retirement guidance during major life transitions
And more!

Resources:

Connect with Eric Blake:

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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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