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How to Make Yourself Into a Learning Machine

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

Mar 3, 2020 · 13 min readUpdated Aug 28, 2026

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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.

When he started, Shopify had 150 employees supporting tens of thousands of merchants. Now, it has 5,000+ employees and over a million merchants. 

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?

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