S3-EP20: Jeff Hamaoui on Changing Mindsets and Navigating the Messy Middle of Transitions

Apr 23, 2021


Debbie talks to Jeff Hamaoui about transitions during this time of global transformation, messy middles (a real term), mindset management, and the pattern-interrupting power of physical retreats.



Debbie talks with Jeff Hamaoui, Modern Elder Academy Co-founder and Chief Education and Innovation Officer, about getting through the “messy middle” (a real term) of transitions. This time of global transformation is also a time of existential transition for many of us. What comes next – and when? And how? Especially if you are in midlife or older.

The messy middle of any life transition is not easy, or comfortable, to get through. The old has ended but the new has not yet started or is not yet clear. 

If you’ve been listening to the podcast for a while you’ve heard her mention MEA and you might have listened to her interviews with founder Chip Conley. Debbie joined MEA’s online program, Navigating Midlife Transitions, feeling she needed dedicated time and space to reflect on – and make sense of – this pandemic “gap” year. Jeff’s guidance through the program was provocative, so she called him to dive a little deeper.

Jeff, and others who have studied transitions (most notably William Bridges), have identified the “messy middle” as the most challenging phase of a transition. Adopting a mindset of growth and curiosity can help you get through it. This applies equally to transitioning into midlife and beyond. What we used to call “getting old.”

Debbie and Jeff talk about:

  • Why Jeff’s interest in transitions
  • What is a modern elder
  • The anatomy of a transition
  • The concept of messy middles and how to get through them
  • Why a growth mindset is important
  • Pattern interruption – why you need to go to a place to rethink aging and midlife


At the end of the episode, listen for the sound of birdsong and trickling water as Debbie reports back from a recent real-life visit, with her husband Sam, to the MEA campus in Baja Sur, Mexico.


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Thanks to our media partners

Encore.org, our newest media partner, is an ideas and innovation hub tapping the talent of those 50+ as a force for good. Founder and CEO Marc Freedman is an award-winning social entrepreneur and author, most recently, of How to Live Forever: The Enduring Power of Connecting the Generations. Looking for a great gap-year transition program? Check out Encore Fellowships, which match skilled, seasoned professionals with social-sector organizations in high-impact, paid assignments.


Modern Elder Academy is a program dedicated to navigating mid-life transitions. MEA, based in Baja California, Mexico, provides the place and the tools to start reframing your lifetime of experience. Grow whole, not old. Founder Chip Conley is a New York Times bestselling author, award-winning hospitality entrepreneur and a rock star of the mid-life transition movement. His newest book is Wisdom @ Work: the Making of a Modern Elder.


Next For Me is an important new resource for the 50+ crowd focused on rewriting life. Taking a gap year or timeout may be the best way to figure out "what's next" when you're in this stage of life. Founder Jeff Tidwell explains, Next For Me "connects and inspires our generation to evolve our post-50 lives through new work, a new purpose, or a new social contribution."