The Cool Grandpa

Navigating Grandfatherhood and Midlife Career Moves with Mark Aylward – EP 227

In 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 real Clarity
  • Embracing the role of a grandparent without overstepping boundaries

Links

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Affiliate Links

These are links to products and services that I highly recommend AND use. I do get a percentage of the purchases you make.

More than GrandMore Than Grand is an excellent resource for new grandparents AND parents. Listeners of The Cool Grandpa Podcast enjoy 10% off any fantastic products that More Than Grand provides by entering COOLGRANDPA10 at checkout. To visit More Than Grand, click HERE.

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Intentional Grandfathering MasterclassGrandfathers have a unique and meaningful role to play in grandchildren’s development, yet they often find themselves behind the scenes, on the sidelines, or less engaged than they’d like to be. This masterclass delivers a playbook for helping grandfathers level up their influence and impact. Listeners to The Cool Grandpa Podcast can receive 40% off this course by using Cool40 at checkout.

Visit Intentional Grandfathering

Grandparents academyFounded in 2011 by Aaron Larsen as a way to honor his grandparents, GrandparentsAcademy.com is the world’s first and only online academy dedicated to helping grandparents grow meaningful relationships and rich legacies with their loved ones.

Visit Grandparents Academy
Cover for My Grandpa's Grandpa

My Grandpa’s Grandpa

When it is time for bed, Charlie’s grandpa tucks Charlie in. Charlie asks his grandpa many questions about his grandpa’s grandpa. Charlie’s grandpa shares a magical moment as he introduces Charlie to his great-grandpa through fun memories.

 

This is a smooth mouse pad for even smoother browsing. The top lets everyone know that you are a Cool Grandpa or have a Cool Grandpa in your life. The rubber bottom guarantees no slip around the mouse (optical and laser). The mouse pads will serve you for years without fraying or pilling.

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