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How to Make Yourself Into a Learning Machine
Shopify’s director of production engineering explains how reading broadly helps him get to the bottom of things
Oct 25, 2023 · 14 min readUpdated Jun 26, 2026
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Editor’s note: We're approaching the one-year anniversary of the release of ChatGPT, a knowledge and information machine unlike any we have ever before created. As we reflected on the role of knowledge, we also wondered what the future of learning would be. How can we learn in the age of AI? What role (if any) do books have? This interview, which we published before the rise of generative AI, might give us a window.
Imagine this: you’re an 18-year-old with just a high school degree. You immigrate to a new country that speaks a different language, and start work with some of the brightest engineers in the world.
Soon after, you’re thrust into management. Now, you’re leading teams of people who are 10 or 20 years older than you, working on one of the fastest-growing internet companies of the last decade.
You have two options: sink or swim.
That’s the position Simon Eskildsen found himself in early in his career. He left his home in Denmark after high school, and moved to Canada alone to take a pre-college gap year working at Shopify.
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