Navigating Grandfatherhood and Midlife Career Moves with Mark Aylward - EP 227
Release Date: 04/18/2025
Skip Gen Travel with Stefanie Shackelford EP - 251
The Cool Grandpa Podcast
Episode Summary In this episode of The Cool Grandpa Podcast, I sit down with Stefanie Shackelford, founder of Odyssey Travel, to explore how travel has evolved—and why experienced travel advisors matter more than ever, especially for grandparents planning meaningful trips with their grandchildren. With over 40 years in the travel industry, Stefanie shares how travel planning has shifted from handwritten tickets and phone-book-sized fare manuals to today’s digital-first world—while explaining what technology still can’t replace: human insight, experience, and relationships. Together,...
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Raising Tomorrow with Kepler Knott - EP 250
The Cool Grandpa Podcast
Episode Summary: In this episode of The Cool Grandpa Podcast, I sit down with author, father, and former tech entrepreneur Kepler Knott to explore what it means to raise kids in an age of rapid change. Drawing from his book Raising Tomorrow: Talks to Prepare Our Kids for What Lies Ahead, Kepler shares why adaptation, resilience, and values matter more than ever—and how parents and grandparents can guide kids without hovering over them. Together, we discuss how to talk with kids (not at them) about meaning, work, money, technology, relationships, and values. The conversation highlights the...
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Navigating Senior Living with Jeannie Duckworth EP - 249
The Cool Grandpa Podcast
Summary: Choosing senior living for a loved one can feel overwhelming, emotional, and deeply personal. In this episode of The Cool Grandpa Podcast, I sit down with Jeannie Duckworth, co-founder of Blue Magnolia Senior Living Advisors, to unpack what families really need to know when navigating senior care options. Jeannie shares her journey into senior living, shaped by years of hands-on experience inside communities and a deep passion for advocacy. She explains that Blue Magnolia Senior Living Advisors was built to serve families first—offering free, personalized guidance while...
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Leadership Lessons from Santa Claus EP - 248
The Cool Grandpa Podcast
Show Notes: Santa Claus isn’t just a holiday icon—he’s a world-class leader. In this episode of The Cool Grandpa Podcast, I explore four powerful leadership traits modeled by Santa Claus and how grandparents, parents, and team leaders can apply them both at home and at work. Drawing from real-life experiences, generational insights, and leadership wisdom, this conversation reminds us that leadership is less about titles and more about vision, trust, consistency, and joyful service. Whether you’re guiding your family, leading a team at work, or mentoring others, these...
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Grandparenting in the Roman Empire with Dr. Lisa Brunet EP - 247
The Cool Grandpa Podcast
Summary In this episode, I talk with historian Lisa Brunet, whose work explores the hidden world of grandparents in ancient Rome. Together, we unpack what grandparenting looked like 2,000 years ago—how elders shaped family identity, cared for young children, preserved memory through storytelling, and passed on family and cultural traditions. While grandmothers often stepped into hands-on roles, grandfathers frequently became the family's historians and memory keepers—sometimes proudly seeing themselves in a toddler learning to speak or scribble. Lisa explains how Roman law, marriage...
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Bonus Show - How Grandkids Stretch Us: Lessons from Dean Nielson
The Cool Grandpa Podcast
Show Notes You are going to enjoy listening to the very first interview that I did for The Cool Grandpa Podcast. This episode originally aired back in May of 2020. This conversation still resonates with me, my wife Karen, and many other listeners to the podcast. If you heard it before, I hope you enjoy it again. If this conversation is new to you, you will get a lot of wisdom from Dean. In this heartfelt, post-Thanksgiving episode, I sit down with longtime friend and seasoned grandfather Dean Nielson. Dean—a Lean Six Sigma project manager, Eagle Scout mentor, devoted husband, dad of four,...
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Lead Like a Grandpa: The Heart-Centered Leadership Your Team Needs EP - 246
The Cool Grandpa Podcast
Summary In this solo episode, I explore how the natural strengths of intentional grandfathers — presence, curiosity, encouragement, patience, and wisdom — translate into powerful leadership skills in today's workplace. Using stories about Legos, pancakes, and real-life team challenges, Greg reframes proven leadership ideas from Dale Carnegie, John Maxwell, and Dan Miller into an accessible, heart-first approach he calls Grandpa Leadership. Listeners will learn how to build stronger connections with their teams, empower younger employees, guide people through mistakes, and cultivate...
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Empowered Caregiving; with Renee Balcom EP - 245
The Cool Grandpa Podcast
In this follow-up conversation, I welcome back healthcare advocate and tech CEO Renee Balcom to discuss how grandparents and families can take control of caregiving decisions before a crisis hits. Renee shares practical insights on avoiding common caregiving mistakes, understanding medical and legal authority, and how technology, such as her new platform, Scroll.care, is changing the way families find trustworthy care providers. We explore why planning for aging is not about fear—but about empowerment—and how grandparents can build a legacy of compassion, preparedness, and advocacy...
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Caring Grandparents Insights from Neil Taft EP - 244
The Cool Grandpa Podcast
“Thou shalt honor the parents of your grandchildren. That’s the most effective way to build lasting family relationships.” — Neil Taft 🧩 Episode Summary In this heartfelt and insightful episode, I reconnect with author and grandparenting expert Neil Taft to explore the evolving role of grandparents in modern families. Neil shares insights from his newest book, Caring Grandparents, and explains how grandparents can both care about and care for their grandchildren. We discuss the emotional and financial realities of grandparents raising grandchildren, the importance of respecting...
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Millennial Grandparents; Insights From James Lott Jr. - EP 243
The Cool Grandpa Podcast
I welcome back longtime friend and repeat guest Dr. James Lott Jr., host of to discuss the rise of millennial grandparents and how shifting generational dynamics are reshaping modern family life. Together, we unpack everything from Millennials' and Gen Z’s futures as grandparents to how technology, social media, and evolving family structures have changed what it means to be a grandparent today. The discussion is full of humor, honesty, and insight — a lively cross-generational conversation about love, legacy, and laughter. Highlights: Why millennials are redefining what “young...
info_outlineIn this heartfelt and candid episode, I sit down with career coach, entrepreneur, and proud grandfather Mark Aylward. They dive into the complexities of becoming a grandfather under unexpected circumstances, the power of simply "showing up," and how intentional presence can transform relationships.
Mark also shares powerful insights from his decades-long career in IT recruitment, his transition into career coaching, and his mission to help midlife professionals reclaim Clarity, confidence, and courage.
Expect real talk, big laughs, and memorable moments—from vocabulary lessons with his grandson to a great story of a friend calling NBA executives pretending to be Larry Bird. Whether you're navigating grandparenthood or a late-career pivot, this episode offers something valuable and inspiring.
🔑 Key Topics & Takeaways:
- The surprise and beauty of becoming a grandfather at 17
- Supporting a son through addiction and young fatherhood
- The importance of presence and modeling for children and grandchildren
- Tree climbing and gratitude: bonding through simple routines
- The broken hiring process and how to bypass the gatekeepers
- Why confidence is often the missing piece in career transitions
- Helping professionals in their 50s+ rediscover purpose and direction
- The art of storytelling in job interviews and career branding
- Why asking "What do you mean by that?" unlocks absolute Clarity.
- Embracing the role of a grandparent without overstepping boundaries
Links
- MarkAylward.com – Website, coaching info, and newsletter
- The Imperfect Men's Club Podcast – Real talk for men in midlife
- Use this link to book Mark's Free 30-Minute Coaching Call: https://calendly.com/aylwardmark/30min?month=2025-04