How do you act effectively in times of uncertainty? One way is by asking yourself better questions. In this conversation, Harry shares a framework to do just that.

Show notes:

- Masters of Uncertainty by Rich Diviney
- 8 1/2
- Cascading Choices Framework by Roger Martin

Implementing changes – especially irreversible and potentially catastrophic changes – requires humility and understanding. In this conversation, we discuss Chesterton's fence and the art of mindful change-making.

Show notes:

• The Thing by GK Chesterton
• Chesterton’s fence
• Seeing Like a State by James C. Scott
• Systemantics by John Gall
• Gall’s law
• Christopher Alexander
• Drift Into Failure by Sidney Dekker

Acting skillfully entails choosing the right thing to do at any given moment. But these actions must also serve higher-level goals. In this conversation, we explore the relationship between both levels of priorities.

Show notes:

• On Grand Strategy by John Lewis Gaddis
• The New How by Nilofer Merchant
• Playing to Win by A.G. Lafley and Roger Martin
• Four Thousand Weeks by Oliver Burkeman
• Innovation Games by Luke Hohmann

Mental models are key to thinking and acting skillfully. But the phrase "mental models" itself has several meanings. In this conversation, we explore models of mental models – and land on one with practical implications for your life.

• The Power of Impossible Thinking by Yoram (Jerry) Wind, Colin Crook and Robert Gunther
• Indi Young
• The Informed Life ep. 82: Indi Young on Time to Listen
• Mental Models by Indi Young
• Farnam Street
• The Great Mental Models Series by Shane Parrish
• Mistakes Were Made (but Not By Me) by Carol Tavris and Elliot Aronson
• Charlie Munger
• Immunity to Change by Robert Kegan and Lisa Lahey
• Diagnosing Your Own Immunity to Change by Robert Kegan and Lisa Lahey (pdf)
• Minds At Work
• Liminal Thinking by Dave Gray

Relying solely on data for decisions is limiting; integrating intuition and diverse insights enhances judgment and outcomes.

Show notes:

• Libby
• Alchemy The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life by Rory Sutherland
• The Fountainhead by Ayn Rand
• Nexus: A Brief History of Information Networks from the Stone Age to AI by Yuval Noah Harari
• How to Measure Anything by Douglas Hubbard
• Drift into Failure From Hunting Broken Components to Understanding Complex Systems by Sidney Dekker
• Embracing the Unexpected: Creative Transformation Amid Rapid Change
• Creativity, Inc. (The Expanded Edition) by Ed Catmull and Amy Wallace
• Toyota Production System

Harry shares an extreme personal experience in service to exploring the question: How can we act skillfully in unfamiliar circumstances?

Show notes:

• An introduction to Ambient Music by Jon Dale
• Spinning Away by John Cale & Brian Eno
• The Age of Surveillance Capitalism by Shoshana Zuboff
• Steve Jobs introduces the iPhone (YouTube)
• Zen Mind, Beginner’s Mind by Shunryu Suzuki
• Dunning–Kruger effect
• Robert Montoye - LinkedIn
• Extreme Ownership by Jocko Willink and Leif Babin
• Extreme Ownership Academy
• The Informed Life episode 75: Hans Krueger on the Cycle of Emotions
• Waking Up app

Exploring the balance between self-deception and reality in goal setting and navigating chaos in professional settings.

Show Notes:

• MIT Professional Education
• Creativity, Inc. (The Expanded Edition) by Ed Catmull and Amy Wallace
• Alvin Toffler
• High Output Management by Andrew S. Grove
• John Cutler (LinkedIn)
• The Hitchhiker’s Guide to the Galaxy by Douglas Adams