In my role on the Editorial team, I end up touching a lot of different parts of Automattic. I work on learning resources, company blogs, highlighting great users, longform publishing, and brand work, with the occasional theme and conference design thrown in. This sort of variety is absolutely amazing, and one of my favorite things about working here.
Of all the projects I get to work on, my favorite thing to do may be illustrations for Longreads. It’s lovely to focus on reading and reflecting on stories, and to have the freedom to explore and experiment with visual representation.
I’ve done over a hundred illustrations for Longreads over the years, and I thought I’d share a few notes on the concepting process I go through for each one.
I always start by reading the story (duh!). While reading, I take note of all the visuals that pop into my head along the way. Most of them will end up being tossed out, but usually there are a few that help build the base of the illustration.
For example, we recently published an essay where Jami Attenberg describes her battle with flight anxiety. Here’s the list I jotted down while reading her piece:
- airplane seats
- pill bottles
When I’m finished reading the story, I run through a series of mental exercises that I picked up years ago in my “Visual Communication” class from design school. VisCom (as we called it) was a required course for all Design, Illustration, and Advertising majors, since at their core, all of those fields center around utilizing visuals to convey or enhance an idea. We were taught about symbolism, juxtaposition, and how to use use color, shapes, and text to get a message across. Here are the questions I ask myself:
- Are any of these items a common symbol? If so, does it represent something that relates well to the story?
- Can one of these items be turned into a new symbol?
- Can I smash some of these images together to make something new?
- Is there a scene from the story that I can build using these images?
My favorite of the bunch is the “smash things together” exercise. This usually involves taking two seemingly unrelated things and combining them create greater meaning. In the case of Jami’s essay, I smashed clouds together with Xanax pills to depict the anxiety-ridden, xanax-fueled flights she described throughout her story.
Another great example of this approach is the illustration I did for Alexander Chee’s piece, “Our Well-Regulated Militia.” I smashed together a map of the United States and a gun rack to echo the article’s statement about the prevalence of guns in America:
This technique doesn’t always work, but it does help kickstart creative thinking, and can help generate other solutions. I often run through 2–3 ideas for each illustration before finding one that sticks.
We’ve been building up our publishing pace and coverage lately at Longreads, and illustration plays a key part in making this successful. Our illustrations help attract readers, and if done well, they can amplify the message of the story itself. We’ve been bringing in some amazing freelance illustrators lately, and I want to close by showcasing some of the great work they’ve been doing too: