Chain of Learning: 72 | Finding Clarity Through the Messy Middle: Reflections from My Book Retreat with Betsy Jordyn (BONUS)

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The messy middle is part of the learning process.

It’s the point where what worked before no longer fully fits—but what comes next is not yet clear.
Where your thinking is still forming, your ideas are evolving, and the answer has not fully emerged.

And while it can feel uncertain, this is often where the deepest continuous learning happens.

In this behind-the-scenes bonus episode on Chain of Learning, I share a live conversation with, Betsy Jordyn, my business coach and strategic thinking partner, recorded on the final day of a working retreat earlier this month. 

We pull back the curtains and invite you into our unscripted reflections from working through the messy middle of shaping my next book—and the leadership (and life) lessons that continue to emerge through the process.

Tune in to hear the real-time learning, reflection, and refinement happening as I shape the ideas behind my next book.

You’ll learn:

  • Why the messy middle is often a necessary part of continuous learning, growth, and effective change leadership
  • How to recognize when forcing clarity too early limits stronger thinking from emerging
  • What it looks like to let ideas evolve instead of defending what came before
  • How collaboration and outside perspective sharpen your judgment and deepen your thinking
  • Why modeling your own learning process creates stronger conditions for learning in others
  • How to stay engaged in uncertainty without rushing to jumping to answers too quickly

ABOUT MY GUEST:

Betsy Jordyn is the founder and CEO of Betsy Jordyn International, a strategic branding firm that helps transformational consultants and coaches refine their messaging, positioning, and offers to accelerate their success and amplify their impact. She is also the host of the Consulting Matters podcast and a sought-after speaker and trainer on brand strategy, executive influence, and the business of transformation.

Will you help me?
I have a quick favor to ask. I’m conducting research for my next book and would love to get your insights on people-centered, learning organizations and the leadership that creates them. The survey takes just 5 to 10 minutes and your responses will directly shape the book and a future Chain of Learning podcast episode.
-> Take the Survey here, open through May 22.

IMPORTANT LINKS:

TIMESTAMPS FOR THIS EPISODE:

01:16 The hidden reality of creativity and why books are written multiple times
02:39 What the messy middle feels like and why this stage matters more than we think
05:04 Re-centering leadership on what’s within your control in a world of constant change
06:00 Why influence isn’t about forcing change, but creating conditions for growth
08:12 Reframing resistance and what people actually need to move forward
10:06 How to keep evolving instead of staying stuck in old ways of thinking
12:26 The process of writing a book and getting clarity on the what the book is about
16:04 Why growth often requires releasing what once worked
17:09 Benefits of collaborating in person vs. using AI as a thinking partner
18:07 Why learning can’t be forced, but we need to allow space for insight
22:07 The concept of omotenashi and looking at a lens of caring from a human angle
24:14 The meaning of Intention = Heart + Direction to create the conditions for learning
29:15 What changes when you respect others’ agency instead of driving direction
32:19 How to have empathy and not push your agenda when leaders are not “bought in”
33:01 Why your expertise can become a barrier to connection and clarity
35:46 How different perspectives reveal whether your message actually lands
38:08 Moving beyond the lingo to prevent barriers
43:27 Why growth requires releasing identities, ideas, and ways of working

Participate in my Survey:
LINK HERE
Thank you