Financial Services – The Simply Retirement Podcast

10 Retirement Websites Every Woman Should Bookmark (Ep. 128)

By The Simply Retirement Podcast | October 28, 2026

Social Security, Medicare, old retirement accounts, long-term care, and even your credit report can all raise questions as retirement gets closer. Knowing where to find reliable information can make those decisions feel much more manageable.

In this episode, I share 10 websites I believe every woman should bookmark for retirement planning. I explain where to review Social Security records, understand Medicare, search for forgotten retirement accounts and unclaimed property, research long-term care and caregiving resources, check a financial professional’s background, and review your credit reports. My goal is to help you gather useful information, spot anything that may need attention, and ask better questions before making important retirement decisions.

Key points:

How to review your Social Security earnings record, benefit estimates, and other important account information
Where to learn about Medicare coverage, enrollment, costs, and free local health insurance counseling resources
How to search for forgotten 401(k)s, pensions, bank accounts, checks, insurance proceeds, and other property
Where to find caregiving and long-term care resources and understand services that may be available locally
How to check financial professionals and credit reports for disclosures, errors, unfamiliar accounts, or concerns
And more!

Resources:

Websites:

Connect with Eric Blake:

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What Women Are Telling Us About Retirement: Their Goals and What Keeps Them Up at Night (Ep. 127)

By The Simply Retirement Podcast | October 21, 2026

Retirement can bring a surprising mix of excitement and uncertainty.

Having enough money matters, but so do the questions about health, purpose, family, taxes, and whether you’re making decisions you’ll feel comfortable living with.

In this episode, I share what women in the Simply Retirement Community told me about their biggest retirement goals and worries. I walk through themes including financial independence, travel, health, Social Security, Medicare, taxes, and investment decisions. I also explain why defining what you want retirement to look like can help you ask better questions, evaluate your choices, and understand how the different pieces of your retirement plan fit together.

Key points:

How defining what you want your money to support can make the question of “enough” more personal and useful
Why travel, health, mobility, independence, family, purpose, and legacy shape retirement beyond the numbers
How Social Security, Medicare, healthcare, taxes, and long-term care create overlapping retirement decisions
Why understanding a financial recommendation includes asking what it costs, what you give up, and what could change
How education, good questions, and clear explanations can help you make decisions when retirement feels uncertain
And more!

Resources:

Connect with Eric Blake:

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Retirement for Women: Identity, Purpose, and Life After Work – Part 2 (Ep. 126)

By The Simply Retirement Podcast | October 14, 2026

What happens when the career that shaped your schedule, relationships, and identity is suddenly no longer part of your everyday life? Preparing for retirement can mean thinking beyond the financial pieces.

In this episode, I continue my conversation with Kelly Ottman, PhD, Professor at Milwaukee School of Engineering and Executive Leadership Coach at Leadership Portals, LLC, about preparing for the personal transition into retirement.

We explore how women can rethink identity beyond a job title, create new sources of purpose, maintain important relationships, and build structure before leaving work. Kelly also shares practical ideas from her research, including practicing retirement habits, creating a curiosity list, finding mentors and role models, and becoming more comfortable with a different pace of life.

Kelly discusses:

How women can begin separating their identity and sense of purpose from a professional title before retirement
Why relationships and social connections deserve intentional preparation before leaving the workplace behind
How practicing new routines, hobbies, health habits, and social activities can make the transition feel more familiar
Why a curiosity list can help women explore interests and possibilities they haven’t had time to pursue before
How mentors, role models, friends, and family can provide valuable support when retirement starts to feel overwhelming
And more!

Resources:

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Connect with Kelly Ottman:

About our Guest:

Dr. C. Kelly Ottman is an executive coach and consultant, keynote speaker, scholar, and award-winning professor with more than 25 years of experience developing leaders across the leadership lifespan. A former healthcare executive, she brings expertise grounded in a prestigious two-year executive development fellowship and a PhD in Organizational Leadership and Adult Education from the University of Wisconsin Madison. As an executive coach/consultant, Dr. Ottman partners with local, national, and global organizations and boards. Her clients range widely—from Fortune 500 executives to executive steel leaders, and even executive nuns. She has extensive global experience, with a particular focus on Asia, especially China and India. With a passion for service, she is currently the volunteer Executive Leadership Coach Coordinator for the WE Empower United Nations (UN) Sustainable Development Goals (SDG) Challenge and the International Leadership Association. Emerging from the intersection of her coaching and academic work, Dr. Ottman recently completed a groundbreaking study on executives and the transition to retirement. This was supported as part of a protracted leave (research-focused sabbatical) as a business Professor at Milwaukee School of Engineering University (MSOE). To activate her research and extend her current coaching and consulting to include leadership beyond retirement, she is a Certified Professional Retirement Coach (CPRC) through the Retirement Coaches Association.

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Retirement for Women: Identity, Purpose, and Life After Work – Part 1 (Ep. 125)

By The Simply Retirement Podcast | October 7, 2026

Retirement can look settled financially and still leave you wondering who you’ll be when your career and title change. How do you prepare for the parts of retirement that don’t show up on a financial statement?

In this episode, I sit down with Kelly Ottman, PhD, Professor at Milwaukee School of Engineering and Executive Leadership Coach at Leadership Portals, LLC, to explore her research on how executives experience retirement. We look at why women may enter retirement with broader identities and social networks, yet still struggle with losing credibility, purpose, and voice.

Kelly also shares what she learned about spending anxiety after years of saving, the role of financial and non-financial planning, and why retirement may be better viewed as a period of renewal, repurposing, and possibility.

Kelly discusses:

Why retirement can challenge identity even when someone feels financially prepared to leave a long career
How women’s broader social roles can support retirement while the loss of professional credibility still hurts
Why some retirees know they have enough on paper but still need confidence and permission to spend more freely
How financial planning and non-financial planning can address different parts of the retirement transition
Why retirement plans need room for changing health, family circumstances, relationships, and personal priorities
And more!

Resources:

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Connect with Kelly Ottman:

About our Guest:

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Social Security Rules Women May Not Know: Survivor Benefits, Retirement Age & Taxes (Ep. 124)

By The Simply Retirement Podcast | September 30, 2026

Social Security rules can look straightforward until survivor benefits, retirement ages, taxes, and your personal history start overlapping.

Understanding where these rules came from can help you recognize which details deserve a closer look before you file.

In this episode, I look back at how Social Security has changed and why that history still affects women making retirement decisions today. I explain why some people have two different full retirement ages, how survivor and divorced-spouse benefits developed, and how rules around remarriage have changed. I also cover Social Security taxation, cost-of-living adjustments, and several numbers that haven’t kept pace with inflation.

Key points:

Why retirement and survivor benefits can have different full retirement ages for the same person
How survivor benefits developed and why a spouse’s filing age can affect the surviving spouse
Why a 10-year marriage remains an important threshold when considering benefits from an ex-spouse
How Social Security taxation thresholds have remained unchanged even as incomes and costs have risen
Why understanding today’s Social Security rules can help women make more informed retirement decisions
And more!

Resources:

Connect with Eric Blake:

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Rethinking Retirement: Building a Life on Your Own Terms (Ep. 123)

By The Simply Retirement Podcast | September 23, 2026

What happens when the life you planned no longer fits the person you’ve become?

Retirement planning can create space to reconsider where you live, how you work, and what you want your next chapter to look like.

In this episode, I talk with Meg McKeen, Founder and Principal Consultant at Adjunct Advisors LLC, about the personal and financial decisions that reshaped her life. Meg shares how divorce pushed her to understand her finances and become her own advocate, how she eventually left corporate life and became a full-time traveler, and why she’s learning to balance saving for the future with living today. We also explore practicing retirement, spending after years of saving, and giving yourself permission to choose a path that may look different from everyone else’s.

Meg discusses:

How divorce became a turning point for learning to make financial and personal decisions independently
Why understanding everyday expenses helped her see that supporting herself financially was possible
How leaving corporate life and selling her home eventually developed into five years of full-time travel
Why practicing a different lifestyle before retirement can help clarify what you actually want from it
How learning to spend intentionally can be just as important as building the habit of saving for retirement
And more!

Resources:

Connect with Eric Blake:

Connect with Meg McKeen:

About our Guest:

Meg McKeen is the founder and principal consultant of Adjunct Advisors LLC and the host of the Bound & Determined podcast. After building a traditional corporate career in the insurance industry, Meg stepped away at 39, took a year away from work, and launched her company in 2018.

Her personal path has included marrying young, divorcing at 30, and building an independent life without children. In 2021, Meg sold her Chicago home and many of her belongings to begin traveling full-time. She has since spent meaningful time in every state except Alaska while continuing to run her business.

Meg’s story encourages women to question long-held assumptions about work, home, success, and retirement. She also brings an honest perspective on the planning, uncertainty, and tradeoffs involved in creating a less traditional next phase of life.

Meg McKeen and Adjunct Advisors LLC are not affiliated with Blake Wealth Management or RFG Advisory.

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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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