Why was it so important give Shopify a new Illustration style?
Illustration is a communication tool with three super powers. It can add clarity to a complex idea. It can link concepts to the words we’ve assigned them within our respective products (aka on-boarding). And, it can capture the values and traits of a brand in a single voice, shift the tone depending on the situation, and speak directly to the user.
The existing illustration style, while visually pleasing, did little to augment the content, and only repeated the existing copy instead. It was limited in it’s ability to communicate complex ideas, and it did not accurately map to the Shopify values or principles.

The Documentation:
I’m pretty sure future Meghan is going to be stoked that we took the time to document our decisions. As the team evolves, I would consider it a failing on my part if there is no means for the next person to step in and easily get up to speed. There is no doubt that it is a useful tool for sharing what we’ve created, some day. To be honest, when there are three just three of us who invented this illustration style—who spend 110% of our time drawing in this illustration style, talking about this illustration style and thinking about this illustration style—we don’t exactly need to refer back to the style guide on the reg.
But where the style guide, and documentation is powerful, particularly in the early stages of creating a new illustration style, is alignment. It starts with “Okay, I’m writing this down, we’re all on board with these colours, right?” — an easy check. Every time the style guide grows, the questions get a little bit harder, moving from “rounded or square caps?” to “hey there’s something to the objects we choose to illustrate that makes them feel like they belong together. What is it?” or “So you know how we’re always a little haphazard, but, not too much..?”