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:

• Get Your FREE Simply Retirement Roadmap
• 2026 Tax and Retirement Planning Cheat Sheet

Connect with Eric Blake:

• www.TheSimplyRetirementPodcast.com
• Join the Simply Retirement Newsletter
• Ask a Question or Suggest a Topic for the Podcast
• Blake Wealth Management
• YouTube

Connect with Kelly Ottman:

• LinkedIn: Kelly Ottman
• Website: Kelly Ottman – Leadership Portals

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:

• 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:

• Get Your FREE Simply Retirement Roadmap
• Ultimate Guide to Women’s Social Security Success
• #24 – Understanding Spousal (and Ex-Spousal) Social Security Benefits
• #37 – Top 5 Questions on Social Security Survivor Benefits
• #47 – Three Game-Changing Social Security Strategies
• #54 – How Social Security Gets Taxed: What You Need to Know
• #63 – Social Security Planning After Divorce: Crucial Rules and Mistakes to Avoid
• #109 – Social Security Rules That No Longer Apply

Connect with Eric Blake:

• www.TheSimplyRetirementPodcast.com
• Join the Simply Retirement Newsletter
• Ask a Question or Suggest a Topic for the Podcast
• Blake Wealth Management
• YouTube

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:

• Get Your FREE Simply Retirement Roadmap
• 2026 Tax and Retirement Planning Cheat Sheet
• #17 – Financially Fearless Women with Barb Provost and Maggie Nielsen

Connect with Eric Blake:

• www.TheSimplyRetirementPodcast.com
• Join the Simply Retirement Newsletter
• Ask a Question or Suggest a Topic for the Podcast
• Blake Wealth Management
• YouTube

Connect with Meg McKeen:

• LinkedIn: Meg McKeen
• Website: Adjunct Advisors
• Instagram: @megmckeen
• Podcast: Bound & Determined

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.