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:

• Get Your FREE Simply Retirement Roadmap
• Facebook Group: The Simply Retirement Community
• Episodes Category: Investing in Retirement
• Episodes Category: Healthcare and Medicare
• Episodes Category: Social Security

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 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:

• Get Your FREE Simply Retirement Roadmap
• Ultimate Guide to Women’s Social Security Success
• #56 – What Will You Do with Your 1,000 Hours a Year in Retirement?

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.

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.