I recently did an experiment. I allowed files and folders to accumulate on my computer for a month – just let them pile up without organizing anything. By the end of that month, I had 222 individual items scattered across my desktop and downloads folder. The accumulated files were genuinely diverse… Financial documents: personal tax…
Six years ago, I attended a week-long course in Northern California called Groundbreakers. Facilitated by Joe Hudson and his wife, Tara, it was one of the most impactful experiences of my life. The experience I had there reshaped my relationship with the “voice in my head,” that is, with my own inner monologue. It helped…
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…
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
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…
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…
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…
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…
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…
I recently came across a Substack post by Venkatesh Rao called Oozy Intelligence in Slow Time that was one of the most insightful I’ve ever read for understanding the nature of Artificial Intelligence. We tend to think of Artificial Intelligence as being in an arms race with Human Intelligence. Which one is smarter? When will…
Like so many others, I’ve spent the past year exploring and experimenting with emerging AI tools. Throughout that time, there has been one question I’ve been trying to answer: Will AI replace the need for Second Brains entirely? A lot of people seem to think so, and I admittedly have a self-interested motivation: to decide…