Name: Stop Trying to Figure Life Out. Start Figuring Yourself In.
Uploaded: 2026-07-22T07:39:10.000Z
Duration: 4526
Description: What does real leadership require when the old maps stop working? In this conversation, Dave sits down with leadership expert and coach Andy Cahill to explore...

What does real leadership require when the old maps stop working? In this conversation, Dave sits down with leadership expert and coach Andy Cahill to explore the fantasy that someone out there has life figured out, and the alternative Andy offers instead: learning to figure yourself in. They get into why so many of us are pulled toward crisis and quests without meaning to be, what it looks like to drop the change agenda in coaching and in relationships, and how strength and gentleness work together rather than against each other.

In this episode:

-The fantasy that someone else has it figured out
-Figuring yourself in versus figuring life out
-How leaders unconsciously create the crises they thrive in
-The change agenda, and what it costs a coach or a parent
-Holding strength and gentleness together
-The micro pause, and why real reflection happens in the moment
-Book recommendations on embodied cognition and the psychology of environment
The Extended Mind: The Power of Thinking Outside the Brain — Annie Murphy Paul
The Architecture of Happiness — Alain de Botton

Chapter Timestamps

⏱ CHAPTERS
00:00 — Introduction
04:57 — The fantasy of someone having it figured out
05:26 — Figuring yourself in
17:15 — The crisis I was creating
19:20 — The change agenda
33:52 — Strength and gentleness
46:47 — The micro pause
1:13:08 — Book recommendations
[00:xx] — Closing question

______

Andy Cahill is a leadership development expert who works with purpose-driven executives and entrepreneurs. Past and current clients include Microsoft, Marriott International, Alnylam Pharmaceuticals, Patagonia, lululemon athletica, The Obama Foundation, MIT, and a variety of A-to-D series funded startups in the tech and social impact sectors.

Andy earned his master’s degree in leadership from the Harvard Graduate School of Education. He is a professionally certified coach (PCC) with the International Coaching Foundation, and he is also a Level 2 certified Internal Family Systems practitioner.

He is also the host of Wonder Dome, a podcast with a global listenership that explores explores the intersections of philosophy, psychology, science, and spirituality. And his critically acclaimed science-fiction novel Gradient brings a mythic frame to the interplay of human and artificial intelligence, surfacing themes of leadership, cultural adaptation, identity formation, technological innovation, and collective resilience in the face of loss.

Website: https://wonderdome.substack.com/
LinkedIn: / andrewjcahill

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