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Building a Second Brain book under a microscope

3-Year Update: A Financial Analysis of My Book’s Unit Economics

Series Navigation: The Making of a Bestseller: A Behind-The-Scenes Look at the Creation of Building a Second Brain

A Guide to the Claude 4 and ChatGPT 5 System Prompts

One of the most influential yet under-appreciated parts of how large language models work is something most people never see: the system prompt. This is the block of hidden instructions given to the model before it ever receives your input. It establishes the model’s tone, boundaries, and behaviors. You can’t change the system prompt, but…

The Voice-Only Mid-Year Review: Testing the Limits of ChatGPT Voice Mode

I recently set aside some time to do my mid-year review, a ritual I complete around July each year, and noticed that I felt some resistance to it. In fact, I realized that I’ve always somewhat resisted it. Since I’m currently writing a book on the subject, I decided to explore why. My first guess…

A Brief History of the Annual Review

When I began writing my next book more than a year ago, on the topic of “annual life reviews,” I assumed that the practice was a fairly recent invention. Maybe it came from the self-help movement of the 1970s. Or from corporate performance reviews. At most, I figured it might trace back to Ben Franklin…

Finding Perspective at the Edge of the World: 10 Days in Antarctica

I lifted my eyes from the journal I was writing in on the balcony of my hotel room, just in time to witness a towering block of ice split in half, splintering along its length with a thundering crack. The iceberg it was part of shuddered, throwing off a shimmering coat of frost from its…

Mushroom Trip: My First Experience with Psilocybin-Assisted Therapy

I’ve noticed that psychedelic medicine has been on the rise in California and other parts of the U.S. over the last few years, and have heard reports from a handful of friends and acquaintances about the incredible results they’ve had from ketamine, MDMA, and psilocybin. In our new home of Valle de Bravo, Mexico, I’ve…

Life and Death on a Scorched Planet: What I Learned From “The Heat Will Kill You First”

I remember the exact moment I was radicalized about climate change. Standing on the front porch of our new home in Southern California in the summer of 2020, I watched the sky turn a burnt orange as wildfires blazed in the inland summer heat. The particles of smoke didn’t just fill the air—they filled our…

My 4-Stage System for Learning Anything New

You discover something fascinating—maybe it’s vibe coding, sustainable investing, or sourdough baking. Your excitement builds as you imagine mastering this new skill. But then reality hits: Where do you even start? The internet offers endless tutorials, courses, and “ultimate guides.” Your bookmarks folder grows heavy with resources you’ll “definitely check out later.” Weeks pass, and…

How a Small Mexican Town Became My Template for the Ideal Place to Live

We’ve been living in Valle de Bravo – a mountain town a couple of hours outside Mexico City – for 9 months now. I’ve lived in 5 countries for at least 6 months each, and traveled in another 20, and I think this is the most perfect place I’ve ever encountered for an expat family…

What J Dilla and Early Hip-Hop Teach Us About AI and the Future of Creativity

In 1997, a young hip-hop producer from Detroit named J Dilla did something that violated every rule in music: he programmed his drum machine to play “off beat.” Not just slightly off, but deliberately off—breaking up the rigid timing that had governed musical performance in every genre. What happened next confounded the music industry. Instead…

Introducing Death Clock (And My First Experience with Vibecoding)

I’m proud to introduce Death Clock, a life expectancy calculator that predicts the day of your death based on 17 personalized variables. Give it a try for free! This is not only the first “app” I’ve ever created myself, but also my first experience with AI-assisted coding, which has become known as “vibecoding.” I can…

Productive Disorder: The Hidden Power of Chaos, Noise, and Randomness

In the early 1700s, Central Europe faced a crisis: the forests were running out. An explosion in mining, shipbuilding, and early industry had devastated old-growth forests that had stood for many centuries. Meanwhile, the population was exploding as well, creating demands on forests that clearly couldn’t be sustained for long. The kingdoms of Prussia and…

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Dedicated to Exploring the Frontier of Modern Productivity