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Hello!
Welcome back to Action Items a series of articles where we condense and extend each of our interviews into actionable bullet points—only for paid subscribers.
This week we’re covering one of our most popular interviews ever: How to Build a Learning Machine with Simon Eskildsen.
Simon is a curiosity machine, and he’s built a collection of systems to help him learn new things and apply everything he knows. He uses Readwise, Anki, and a custom-built Zettelkasten at a world-class level—meaning this interview is filled with great takeaways.
Today’s Action Item is 699 words—that’s 3 minutes and 29 seconds of actionable learnings.
Let’s dive in!
📖 Progress Over Process
Simon wants to have a T-shaped personality—so he reads widely rather than deeply.
He reads 30-50 books a year, but he doesn’t follow a fancy process to help him prioritize what to read next. Instead he:
Follows whatever is most fascinating to him at the time
Reads about the same topic from different authors so he doesn’t have to trust just one person’s perspective
Reads along lines of inquiry to learn about interconnected topics
Sends sample chapters of books to his Kindle to try out before he commits to the entire thing
🤓MY REACTION
Any time you’re dealing with a high-upside, low-downside bet—like which books to read next—it’s usually far more valuable to skip the process and just make a decision.
Simon’s preference to skip the process and just read whatever is most fascinating to him is exactly the right one: if he finds that he’s making a mistake he can always just put the book down
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The Everything bundle now has 10 paid newsletters including Superorganizers. Here are a few articles from around the bundle that you should pay attention to:
How I Spend 5 Minutes A Day on Email, by Nat Eliason in Almanack
Dealing with Co-Founder Resentment, by Jerry Colonna and Andy Sparks
Ask a Journalist, a live event on writing with award winning journalist John H. Richardson, hosted by Rachel Jepsen of The Long Conversation (I’ll be there live too!)
