Action Item: Progress Over Process, Remembering What You Read, Zettelkasten

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

🤓 Dan's Take

• 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.

🧠 Read for retention

If reading is Simon’s superpower, highlighting is his secret weapon. He highlights everything he finds important on his Kindle, which is then automatically imported into Readwise, where he can tag, sort, and track his highlights.

Actionable Takeaway

• He often tags highlights with #flash, and then periodically turns them into flashcards in Anki.
• This helps him resurface the nearly 10,000 he’s amassed so that he can apply them better in his day-to-day life.

📕 Read: How Jeopardy! Champion Roger Craig uses spaced repetition to remember everything