I’m incredibly proud to share news that’s been two years in the making: my next book is coming in Fall 2026! It’s called Life in Perspective, and it represents the culmination of a reflective practice I’ve been refining since 2008: the annual review. If you’ve read Building a Second Brain or The PARA Method, you…
In the summer of 2005, when I was 20 years old, I sat down and wrote one of my first personal goals: “Hold a position in the Associated Student Government of Saddleback College at start of Fall semester (August 22, 2005).” I had just dropped out of college on the East Coast after burning through…
My wife Lauren and I met at a co-working space in San Francisco in our mid-twenties. I was working an entry-level position at a creative consulting agency, at the bottom of the pyramid. Lauren was making $15/hour at an arts nonprofit, living rent-free with her aunt. We both saw no pathway to climb in our…
A new, powerful definition of intelligence is emerging out of the AI field: “boundary intelligence.” I first came across it in this excellent piece To Know Is To Stage by Venkatesh Rao, which appropriately, was co-authored by an LLM. Let me step back and explain what boundary intelligence means (mixing my own words with paraphrasing…
Series Navigation: The Making of a Bestseller: A Behind-The-Scenes Look at the Creation of Building a Second Brain<< Did My Bestselling Book Turn Out to Be a Financial Failure?It has now been 3 years and 3 months since my book Building a Second Brain came out in the U.S., and I’ve just received word that…
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…
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…
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…
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…
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…
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…
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…
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