Summary: Simon built a system to read and remember lessons from hundreds of books on various topics. He uses tools like Readwise and Anki to help retain information and connects ideas in a custom Zettelkasten system. By reading broadly and memorizing key facts, Simon enhances his learning and understanding to excel in his work and personal projects.
And Simon never went to college — he stayed at Shopify and moved up the ranks to lead infrastructure teams that help keep Shopify processing hundreds of thousands of requests a second, day and night.
So how did he do it?
He began to treat his mind like technology infrastructure.
Suddenly, instead of building systems to optimize server performance, he was optimizing his own brain: he was building himself into a learning machine.
Simon realized that in order to level up fast enough to do his work he needed to read — a lot. And not only that, he needed to retain what he read.
So he built an elaborate system to read, retain, and apply the lessons in hundreds of books. And he didn’t just read about infrastructure — he read literature, and scientific history; he read about politics, and philosophy.
Along the way he discovered that reading broadly was the best way to get to the bottom of things, and therefore the best way to get better at his job. (View Highlight)
What I found was that choosing books with a fancy process ends up being more about what I “ought” to read, rather than what I actually just find most fascinating. Eliminating a rigid system helped me pay better attention to what I like and don’t like: getting through the 700 pages of Anna Karenina was a struggle, but I tore through a book on the history of the telegraph in no time.
The one thing I do try to follow is to go on streaks of reading a lot of books on a particular topic around the same time. Doing this is useful because it means I don’t have to just trust one author’s perspective on a particular topic — and helps me connect a lot of facts together, so I can understand things better. (View Highlight)
I read to learn, and I flash to make sure I remember.
I have flash cards on everything from how many kilowatt-hours it takes for a car to travel 100 kilometers, to the definition of the term pollyanna, to the history and culture of the islands of New Caledonia.
It’s powerful to read something and be confident you’ll retain it for a long, long time. To me, flash cards aren’t to memorize random things, or to win at trivia.
They’re there to trigger a concept you’ve already learned, but want to make sure you don’t forget.
I am creeping up on 10,000 cards in Anki, and I’ve been doing this for over 4 years. It’s probably the most impactful habit I have in terms of impact over time invested. (View Highlight)
So that’s what I find helpful — knowing all of these facts becomes a kind of memory connector.
It gives you this web of facts for you to put new information into context, and answer questions with deduction without having to go look something up. (View Highlight)
