Do you find yourself constantly seeking clarity and certainty, even when faced with complex challenges that don't have simple answers? What if that very pursuit of certainty – that comfortable feeling we all chase – is actually blocking your growth, your learning, and your ability to create something new?

This episode explores the counterintuitive idea that confusion isn't something to avoid, but rather something to value as a gateway to deeper learning. What's possible when we release our grip on needing to know and instead embrace the generative space of uncertainty? Together we consider how the most meaningful growth often happens precisely when we're willing to step into discomfort rather than rushing to make it disappear.

Jennifer Garvey-Berger is a thoughtful disruptor who's constantly questioning how we might do business, relationships, family, and leadership better. As CEO of Cultivating Leadership, she's spent decades helping leaders navigate complexity and uncertainty. Jennifer brings a fascinating blend of intellectual rigor and lived experience to our conversation, including her bold experiment of buying a house with twelve friends in France to deliberately create a different way of living. In this episode, you'll discover:

How confusion serves as a necessary gateway to learning and growth
Why certainty, despite feeling comfortable, often blocks our ability to discover new possibilities
How good conversations create something neither person had thought of before
Why crafting a meaningful life requires questioning default assumptions
How deliberate disruption can lead to more authentic ways of working and living
Why play and exploration remain essential elements of leadership at any age
How creating intentional communities can challenge our assumptions about work/life separation
Why our idealism is not something to outgrow but rather a strength to cultivate

Timestamps

(00:00) The Value of Confusion

(08:47) The Quest for a Better World

(14:55) Living Fully vs. To-Do Lists

(32:18) Creating a Unique Living Environment

(40:03) Growth Through Difficulties

(42:28) Giving Less Fucks

Other references:

David Whyte: https://www.goodreads.com/quotes/9100423-what-you-can-plan-is-too-small-for-you-to
Richard Bach: https://en.wikipedia.org/wiki/Illusions_(Bach_novel)
Oliver Burkeman: https://en.wikipedia.org/wiki/Four_Thousand_Weeks:_Time_Management_for_Mortals
Vito Perrone: https://www.gse.harvard.edu/ideas/news/11/09/hgse-remembers-vito-perrone
Thomas Huebl: https://thomashuebl.com/
Heidi Brookes: https://www.cultivatingleadership.com/team-member/heidi-brooks
Andrew Maffett: https://player.captivate.fm/episode/8dc40ef3-104d-4a48-a38e-495ed4650abb
Adam Cooper: https://player.captivate.fm/episode/48bf4ecf-f533-47d3-943e-2445135d473d

You can find Jennifer at:

Website: https://www.cultivatingleadership.com/

LinkedIn: https://www.linkedin.com/in/jennifer-garvey-berger-7b4a264/

Books: "Unlocking Leadership Mind Traps," "Simple Habits for Complex Times," and "Changing on the Job"

Check out my services and offerings https://www.digbyscott.com/

Subscribe to my newsletter https://www.digbyscott.com/subscribe

Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/

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