This page shares my best articles. Not sure where to begin? Below are what many consider to be my “greatest hits” – the essays and articles that have been the most popular or had the greatest effect on readers’ lives.
Decision-Making, Strategy & Mental Models
Full Archives
2023
- March 08 5 Philosophies of History
2022
- March 02 The Four Levels of Organization
2021
- January 13 Certain to Win: The Strategy of John Boyd, Applied to Business by Chet Richards
- January 15 How to Win at Business
- January 27 The Effective Executive Summary
- February 05 My Remote Work Best Practices
- February 19 On 4 Minute Songs
- April 02 The Frontier Thesis
- April 16 Do The Thing You Want To Do
- April 23 Illegible Inefficiencies
- April 28 Fail-Safe Investing by Harry Browne
- May 06 Systemantics by John Gall
- May 07 The Maginot Line Problem
- May 14 The Systems Bible
- May 20 Metaphors We Live By – George Lakoff
- May 28 Taylor’s Machete
- June 04 Festina Lente: Why Slow is Smooth and Smooth is Fast
- June 11 Static vs. Dynamic Games
- June 18 Risk is Not Getting What You Want
- July 02 The Smartest Guys in the Room – Bethany McLean
- July 16 Terminator Mode
- July 16 The War of Art Summary and Notes
- July 30 The Bullwhip Effect and Supply Chain Inflation
- October 22 Subtractive Productivity: How Doing Less Can Achieve More
- October 25 Best Practices for Operational Excellence
- October 29 How to Predict our Economic, Political and Cultural Futures
- December 03 Insurance Makes Wealth Grow Faster
- December 10 The Toyota Production System: A Love Letter
2020
- April 17 Wile E. Coyote Systems
- June 05 The Sand Pile Effect: Why are there weeks in which decades happen?
- June 12 Fire Two Shots, But Never Fire First
- June 15 Tit for Tat Strategy and The Evolution of Cooperation
- June 23 Book Notes – Breakthrough Advertising
- July 10 Become Like Water My Friend
- July 14 The Art of War Summary (and Quotes) by Sun Tzu
- July 14 Reality Has a Surprising Amount of Detail
- July 17 Reality Has a Surprising Amount of Detail:
Business Edition - July 24 The Farmer’s Fable: Free as in Lunch
- July 31 Becoming an Intergalactic Gazillionaire is Harder Than it Looks
- August 14 Nietzsche and Ergodicity
- August 21 The Origins of Political Order Review and Summary
- August 28 RETO: The Robustness Efficiency Tradeoff
- September 04 The Mental Model that Explains Political Revolutions and Financial Crises
- September 18 We Are All Journalists Now
- September 25 The Explore/Exploit Tradeoff: When should I Leap?
- October 02 In Praise of 2/3rd-ism and Messy Compromises
- October 09 Invisible Absorbing Barriers
- October 16 The Farthest Down the Chain Principle
- October 23 History has a History too
- October 30 Metaphorical Proof of Work
- November 06 9 Questions to Ask Before You Start Something New
- November 13 Take the Turkey Out of the Oven
- November 20 Goodhart’s Law: How to not lose $4.6 billion
- November 27 Pull the Andon Cord
- December 04 My Favorite Stone Soup Recipe
- December 18 Trees are the Root of all Evil
2019
- February 28 Markets Are Eating The World
2018
- January 09 Reasons and Persons Summary
- January 10 The Best Books I Read In 2017
- January 10 Debt: The First 5000 Years by David Graeber Summary and Quotes
- January 15 Why Is Bitcoin Valuable?
- February 25 Misbehavior of Markets Summary and Quotes
- June 16 The Most Important Thing Illuminated by Howard Marks Notes and Quotes
- June 16 Market Mind Games by Denise Shull Summary and Quotes
- June 16 The Essays of Warren Buffett Summary and Quotes
- June 16 The Black Swan Book Synopsis, Quotes and Notes
- August 01 When Will Crypto Crash (Again?)
- August 13 The Bitcoin Standard Book Summary and Notes
- August 19 Impro: Improvisation and Theatre Summary and Notes
- September 19 The Best History Books
- September 26 Best Motivational Books of all Time
- September 28 Best Self Help Books
- October 01 The Best Biographies of All Time
- October 10 Best Psychology Books
- November 07 Will Smart Contracts Eat the World?
2017
- June 14 How to Discover Your Core Values List (and Use Them to Make Better Decisions)
- June 17 The Organization Man Quotes and Summary
- July 12 The Truth about How Creativity Really Works
- July 17 Why History’s Greatest Innovators Optimized for Interesting
- July 27 How to Get Into Cryptocurrency: The Best Cryptocurrency Resources
- August 02 The Ultimate Guide to the OODA Loop
- August 10 The Best Philosophy Books
- August 20 How to Prioritize like a Billionaire
- September 05 Everything You’ve Been Taught About How To Read a Book Is Wrong
- September 12 Kaleidoscope Thinking: How to Think Faster and More Clearly
- October 10 The Blockchain Man
- October 11 Denial of Death Summary and Quotes
- October 25 How to Change Your Life using Punctuated Equilibrium
2016
- March 08 Why Product Market Fit is Overrated (and what to focus on instead)
- March 17 Effectual Reasoning: The Little Known Method Entrepreneurs Use to Figure Out What They Want
- April 20 How to Improve Your Mindset
- May 18 How To Plan Your Ideal Day
- July 06 How (And Why) To Find An Online Mastermind Group
- July 20 How to Get Lucky: Focus On The Fat Tails
- August 03 Strengths, Weaknesses, and the Math of Mastery
- August 17 The Unlikely True Story of Ingeborg Francesca Jurkutat
- August 31 Fingerspitzengefühl: What Elite Tank Commanders, Chess Grandmasters, and Entrepreneurs Have in Common
- October 05 The 70% Rule: How to Move Fast and Break Things (and why you should)
- October 19 Speed of Implementation and The Law of Shitty Click Throughs
- November 02 My Favorite Morning Routine
- November 09 The Overton Window and How Creative Business Ideas Arise
- November 30 A Simple Marketing Campaign Checklist
2015
- January 03 3 Steps to Prioritizing Your Reading
- February 07 Welcome to Extremistan. Don’t Be a Turkey.
- March 23 Anything You Want Book Review
- March 23 Be Slightly Evil: A Playbook for Sociopaths Book Review
2014
- January 19 Scaling
- July 12 The Joys of Missing Out (JOMO)
- August 02 The Entrepreneur’s Daily Ritual
- August 16 What is Optionality? How Can Optionality Improve My Performance?
- October 05 The Rise of the Practitioner-Publisher