The Simply Retirement Podcast

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:

Resources:

Connect with Eric Blake: 

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.

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:

Resources:

Connect with Eric Blake: 

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:

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.

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:

Resources:

Connect with Eric Blake: 

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:

Resources:

Connect with Eric Blake: 

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:

Resources:

Connect with Eric Blake: 

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:

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.

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:

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.

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:

Resources:

Connect with Eric Blake: 

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.

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

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.