The Learning Engine 28 May 2026 One Surface Issue, Two Underlying Challenges: A Diagnostic for Every Instructional Leader Your conversation with a teacher looked productive. The teacher was engaged, asking good questions and leaving with a clear next step. You sat with the notes after the conversation, feeling a disconnect between the productivity in the conversation and what would happen next. There was a pattern from the previous three times together – productive-looking conversations with...
10 days ago • 2 min read
The Learning Engine 24 May 2026 Philosophy, Learning, and AI Agents – The Structure Under Every AI Interaction The morning started brightly. Each prompt to the AI agent gave you information, so you seemed to be making progress towards your goal. But, frustration was mounting. Some part of the information was off; sometimes the mistakes were obvious, with other errors arriving subtly. [Five hours later] Frustration has turned to anger, both at yourself and the AI agent. What am I doing wrong?...
14 days ago • 8 min read
The Learning Engine 26 April 2026 Newsletter 043: The Learning Breakdown Diagnostic Greetings and salutations! You are working hard – the effort is genuine and the investment is real – but a gap is still there. Or, a gap has closed somewhat, but not at the rate the effort deserves. That nagging sense that learning could be compounding faster is not impatience; the sense is diagnostic information. Two years ago, a friend named Cedric Chin asked me a question across a table at a Starbucks in...
about 1 month ago • 1 min read
The Learning Engine 28 March 2026 Newsletter 042: A two-year journey started by a single question — “How does it help?” A good day to you! On Saturday, April 6th, 2024, I sat across from my friend Cedric Chin at a Starbucks in the Bukit Panjang MRT station in Singapore. I had been reading Cedric's work at Commoncog for a while (you should also read his work!) — he writes with unusual clarity about expertise, skill acquisition, and how people get better at demanding work. When I found out he...
2 months ago • 2 min read
The Learning Engine 10 March 2026 Newsletter 041: A Walk, a Problem, and a Clearer Direction A good day to you! On a recent morning walk, I finally named a problem I had been carrying for months – and with the naming came the clearest sense of direction I’ve had in a long time. Meetings were happening; interest in my ideas was real. The diagnosis I kept returning to was the same: My framing needed to be sharper, with the vision for The Learning Engine more compellingly described. Somewhere...
3 months ago • 1 min read
The Learning Engine 4 February 2026 Why Learning is the Ultimate Meta-Skill [Video] A good day to you! For the last couple of years I have used this newsletter to share long-form essays regarding how we process information and build capability. These explorations have been a joy to share with you – I hope the essays have been interesting and useful. Recently, my focus has shifted toward the engine that drives every other part of our lives. Most professionals possess systems for finances,...
4 months ago • 1 min read
The Learning Engine 1 February 2026 Learn21 — A Redesign That Expanded What Was Possible A good day to you! I want to share a moment when I saw the principles of learning work deeply — from the results of my physics students. In 2018, I moved from teaching high school physics in South Carolina to an international school in Singapore. I was hired partly to take over AP Physics C — known as one of the hardest courses in the school — from a teacher who had taught the course for over 20 years....
4 months ago • 2 min read
The Learning Engine 30 January 2026 Learn21 — What D1 Soccer Taught Me About Life and Learning A good day to you! I want to share a story of starting from behind — and what the experience taught me about life and learning. In the second semester of my freshman year in college I walked on to a D1 varsity soccer team. I had been a four-year starter in soccer at a small high school in southwest Virginia — plus excelling in football and basketball. I thought I had what I needed to make the D1...
4 months ago • 2 min read
The Learning Engine 28 January 2026 Learn21 — Is This For You? A good day to you! I've been getting questions about Learn21, so I want to answer them directly. "Do I have the time?" Learn21 is about 10-12 hours over 21 days. That's less than an hour a day, with a few days off. Live sessions happen at 11 AM Eastern on Thursdays and Mondays; if you can't make a session, recordings are available immediately. Here's another way to think about the time: Check your screen time right now. How many...
4 months ago • 2 min read
