Time Investing 101 Welcome to the Habit Chess newsletter where I talk about training everyday skills to make moves. read time: ~5-6 minutes In 1913 at Ford’s Highland Park plant, building a single Model T took around 12.5 hours. The work was divided into stations, but workers still had to walk, fetch parts, reposition tools, and move around the car itself. The process worked—but it wasn’t designed for flow. Later that year, Ford’s team introduced a moving assembly line. Instead of workers...
30 days ago • 4 min read
We Fear the Wrong Failures Welcome to the Habit Chess newsletter where I talk about training everyday skills to make moves. read time: ~2 minutes I was watching the Netflix documentary on the James Webb Space Telescope (a $10 billion project that took decades of work). It’s the telescope NASA sent farther into space than any we’ve ever built. There’s a moment where NASA engineer Mike Menzel says something I haven’t forgotten since. “Webb launched with 344 single-point failures.” A...
about 1 month ago • 2 min read
How I Reduce Eye Strain from Scrolling at Night (in 3 Clicks on Your iPhone) Welcome to the Habit Chess newsletter where I talk about training everyday skills to make moves. read time: 2-3 minutes Watch on YouTube or listen on Spotify. I’ve been tracking my sleep on and off for about ten years. I’ve used a wide range of devices. Apple Watch, Fitbit, Whoop strap, Garmin — and the data is all pretty consistent if you run this experiment on yourself. But you don’t even need a sleep tracker to...
2 months ago • 4 min read
Choosing Riverside vs Descript for Podcasting (2025 In-Depth Comparison) read time: 3 minutes Watch on YouTube Choosing the wrong editing software kills podcasts before they even have a chance to begin. If you’re overwhelmed every time you open up the tools you need, that friction is enough to throw you off course once the motivation of being a new show starts to wear off. I’ve been using Riverside and Descript for about five years at this point, and it’s also something that I teach clients...
4 months ago • 4 min read
This Simple Shift Will Make You a Faster Learner Welcome to the Habit Chess newsletter where I talk about training everyday skills to make moves. read time: 2 minutes Watch on YouTube or listen on Spotify. I’ve always been fascinated with how we learn. Especially when it comes to stuff we’re not naturally good at. For me, that was…most things. Wrestling, tennis, boxing, standup comedy, coaching, consulting, podcasting—you name it. But I had a weird obsession with getting better. I wanted to...
5 months ago • 3 min read
25 Ways Charlie Munger Outsmarted Bad Decisions (That You Can Too) Welcome to the Habit Chess newsletter where I talk about training everyday skills to make moves. read time: 3 minutes Watch on YouTube or listen on Spotify. “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.” – Charlie Munger Decision making is one of those skills that quietly impacts everything. If your judgment is sharp,...
5 months ago • 3 min read
The New Way to Set Goals in the AI Era Welcome to the Habit Chess newsletter where I talk about training everyday skills to make moves. read time: 8-10 minutes Watch on YouTube or listen on Spotify. In the era of AI, we need a more sensible way to measure our personal progress. Things are changing so rapidly that using the SMART goal method feels like a Stone age way of doing things. And for most people, let's be honest, it leads to failure or dissatisfaction. Not to say that five year and...
5 months ago • 9 min read
How to Use AI Like a $700/hr Consultant w/ Danoosh Kapadia Welcome to the Habit Chess newsletter where I talk about training the right skills faster. read time: 2 minutes Watch on YouTube or listen on Spotify. When it comes to AI, most of us are doing one of two things: Automating low-level tasks Chasing whatever new tool is trending this week But during my conversation with Danoosh Kapadia, an AI educator who coaches executives on strategic thinking, he said something that instantly reframed...
6 months ago • 2 min read
Hi Reader, I made a dumb mistake that made my amazing mic sound like it was off Temu. For years, I was running my Shure SM7B through a cheap USB adapter, wondering why my audio sounded flat despite having what's supposedly one of the best podcast mics money can buy. I'm embarrassed it took me this long to upgrade my audio interface, but the difference was night and day. Here's when you'll actually need an audio interface and which one to get. USB Mic vs XLR: What's the difference? USB mics...
6 months ago • 2 min read