I've been following some serious business and tech writers for years and these are their serious business illustrations (credits at the end).

This got me thinking, why exactly is the hand-drawn / Microsoft Paint aesthetic so effective? A thread ⬇️
I've always wondered whether this is a passing trend or if there's a functional reason for this style. Whatever it is, it's not short-lived. Newer business and tech writers are also quick to adopt these kinds of illustrations.
Beyond business and tech writers, we see other creators such as long-form essayists and educational YouTubers also keen to illustrate in this style.
One theory is that these types of illustrations proliferated because they're easy to produce and accessible for many creators, but this can be refuted by a couple points.
1. Prominent creators continue to choose this "rough around the edges" style even though they have the resources to employ professional illustrators.

2. Despite looking effortless, these illustrations are not easy to create. https://twitter.com/dwr/status/1296839956153774081
Side note: Another great look into highly produced content that appears effortless is Casey Neistat's video on how he makes his vlogs.
So that leaves us wondering, what exactly are the benefits of this style? Why does it resonate with audiences?
To understand these illustrations, we must understand comics. Conveniently, the book Understanding Comics by Scott McCloud can help.
If we turn to 'Chapter Two: The Vocabulary of Comics', we'll see this series of faces. It is meant to show a spectrum of faces with more realistic faces on the left and more abstract faces on the right.

Scott uses this series of faces to explain two important points.
1. "Cartooning [is] a form of amplification through simplification."
What biz and tech writers, long-form essayists, and educational YouTubers have in common is the need to convey complex concepts. For this purpose, the hand-drawn MS Paint illustrations work wonders because the simplicity draws attention to the concepts rather than the visuals.
2. "Another is the universality of the cartoon imagery. The more cartoony a face is, for instance, the more people it could be said to describe."
While this second point directly applies to the many illustrations with stick figures, I think there's a subtle corollary that extends to the diagrams and graphs that are devoid of faces.
I believe the more hand-drawn an illustration looks, the more familiar the concepts feels. The audience can more readily make abstract connections with their own thoughts and prior observations.
In other words, professional and polished consulting-esque diagrams are less relatable than friendly and cartoony diagrams.
There's a lot of great content from the book Understanding Comics as well as from the creators whose illustrations I've shared in this thread. I highly recommend checking them out. ⬇️
You can follow @iamalexjin.
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