In early 2023, after teaching 6,000 students over six years, I abruptly decided to stop teaching our Building a Second Brain cohorts. Even at that early stage, with the release of the first version of ChatGPT just a couple months earlier, it was clear to me the impact this new technology would have. Almost from…
You’re scrolling LinkedIn during a coffee break. A course creator you know just hit $100K in their first cohort. Another founder you know just closed a funding round. And a peer you met at a workshop got invited to speak at the conference you’ve been attending for years. “They’re so lucky,” you think, closing the…
Anthropic now offers two tools that can BOTH control a web browser AND access your local files. But they work very differently. Here’s the simplest way to think about it: Cowork is the easy option. It lives right inside the Claude desktop app — no setup, no installation, just start chatting and it gets to
At the start of 2025, I dubbed this “The Year of Profitability,” and now that it’s come to a close, I can say we successfully fulfilled that intention. We ended the year with 2.15M in gross revenue, and $650,000 in net profit, for a 30% gross margin. That’s our second-best year ever as a business!…
I’m incredibly proud to share news that’s been two years in the making: my next book is coming on November 3, 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,…
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…
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 it has now earned out its advance! That probably doesn’t mean anything to readers, but to me as an author, it means a ton. It means that the…
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…