Illustrator Shannon May on the Pros & Cons of Freelance Life and Being Female in the Industry

Shannon May is an San Francisco-based illustrator with a long list of clients and an even longer list of accomplishments under her belt. Her works have been featured in publications like McSweeney's, Grantland, Gizmodo, The New York Times, Chronicle Books, as well as more scientific and academic ones such as Institute of Physics, MIT Technology Review, and the Harvard Law Bulletin. In March, she left her full-time position as a designer/illustrator at the San Francisco Chronicle to rejoin the freelance masses. As anyone who's ever left (or wanted to leave) a full-time job for freelance life knows, leaving a consistent and dependable paycheck, workplace, and other benefits is not always the easiest thing to do. I was curious about why Shannon felt like it was the right thing for her to do, and to find out more about what she's working on these days.

A self-portrait by Shannon May

A self-portrait by Shannon May

A lot of illustrators these days do editorial work, but many of them are freelance. What was it like being a full-time staff member at the San Francisco Chronicle

Being at the Chronicle was a really great experience. I worked as an illustrator and designer, so I got to play around with how the illustrations and type could work together and really tried to push that in my layouts. I also got to see the inner workings of a publication, working with writers, editors, and art directors to put out the newspaper every day. There's a lot that goes on behind the scenes that illustrators aren't always privy to! I created more than 300 illustrations over the course of 2 years, so I averaged an illustration almost every other day! I learned a lot just through the sheer volume of work. And my art directors let me do a lot of fun experimentation; I got to embroider a map of San Francisco, do some origami, carve rubber stamps – all for illustrations for the newspaper. These are things I probably wouldn't have done for freelance editorial assignments. I even drew some video game reviews as comic strips!

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Some examples of work that Shannon created while working full time as an illustrator at the San Francisco Chronicle

Some examples of work that Shannon created while working full time as an illustrator at the San Francisco Chronicle

Why did you decide to go freelance again?

It was a really tough decision! It's sort of hard to describe, but there's a subtle difference between being full-time and freelance, in my experience. Being a freelance illustrator, you can have at least some confidence that the art director chose you because they already like your work and want your style for the assignment. Being full-time (and maybe this is just me and my own insecurities), there are a lot of stories that come across your desk that aren't necessarily suited to your work, but you have to find an appropriate way to illustrate it anyway, because the newspaper MUST be published! Sometimes an editor wants the style of another illustrator, but due to financial or time constraints we can't hire them and you're kind of stuck trying to find a way to fudge your work a bit to fit that need. Like sticking a round peg into a square hole! Eventually I just sort of felt that I wanted to spend my time developing my own voice more, which is something I'm still struggling with! Maybe that struggle never really ends. I also was presented with the opportunity to do some teaching, which wouldn't work with a full-time job. All at the same time in some kind of weird confluence of things I got an agent and started getting a ton of freelance work, so it just sort of made sense.

Illustration about Superman's career arc for Grantland Quarterly 8

Illustration about Superman's career arc for Grantland Quarterly 8

And are you still the Art Director at Hyphen (an Asian American arts and culture magazine)?

I am! Hyphen Magazine has been an amazing opportunity. We're a non-profit and everyone who works there is a volunteer, so it's a group of really wonderful and dedicated people. It has been a lot of fun hiring illustrators, many of whom are my good friends and it's great to work with them. I love finding an illustrator whose style seems to work really well with an article; I think I know what I'm going to get from them, but they always surprise me!

In your free time, you still do a lot of drawing. I'm thinking particularly of the drink+draw events that you organize at the Knockout (a bar in San Francisco). Can you explain the event a little more for those who have never been to a drink+draw. What do you like about hosting this event and have you met any artists who you've become closer with because of it?

I still feel like I don't do as much drawing as I should! But yes, I host a monthly drink+draw at the Knockout that is a ton of fun. Basically the idea is that for every drink you buy you get a blank index card, you draw something on the card (we provide drawing materials if you don't have your own!) and put it in a raffle bucket. We randomly pick a drawing from the bucket throughout the evening and that person wins a prize! It's a really nice mix of professional artists (mostly illustrators), people walking by the bar and randomly walking in, and people who've heard about the event online and love to draw but aren't professional artists. So there's a lot of mingling, and it's a great chance for people who might be interested in illustration to meet professionals. There are a few people who I knew peripherally that I know much better now because of drink+draw, like Roman Muradov, Kellan Jett, Mackenzie Schubert, Sophia Foster-Dimino to name a few. Illustration can be a really isolating profession, since you're generally working alone all the time, so it's nice to get out and see some human faces!

An illustration for the New York Times Science section about the diaphragm

An illustration for the New York Times Science section about the diaphragm

You're really interested in science and a lot of your work's been featured in more didactic science and educational publications like the Johns Hopkins Health Review, MIT Technology Review, Stanford Medicine Magazine, etc. Do you pitch to these publications or did they find you? 

I think most of the time they find me somehow, probably through the work I've done for the New York Times, though it's sort of hard to keep track of all the feelers you put out into the world when looking for work! I was really interested in physics in high school but was horrible at math, otherwise I might have pursued that instead of art, so I think that's present in my work. And though I had always wanted to go to art school, I ended up starting college as an environmental science major, thinking it was a more practical career. So science was always something I was really into, though it took a while for it to creep into my illustration work. I think artists and scientists have a lot in common, even though people say the brain is divided between the creative side and the scientific/logical side. I don't really subscribe to that. To me, art and science are just different ways of trying to make sense of the world around us. There's a lot we don't understand! Art tries to capture it visually, science tries to describe it through hypotheses, diagrams and equations. I enjoy the challenge of applying the language of science to other concepts. What kind of diagram can you draw to describe interpersonal relationships, or challenges in education, or inefficiency in the workplace? I'll admit not all of my visual solutions are science-oriented, but it's fun to think about. (Anybody interested in this stuff might want to read Art & Physics by Leonard Shlain.) I also really like the idea of Occam's razor, that a simple solution is usually better than a complex one, and like to apply that idea to my illustration work. How can I communicate the concept with the fewest possible visual elements? 

An illustration of Robin Hunicke for Women's Work

An illustration of Robin Hunicke for Women's Work

You're working on a zine called Women's Work. Can you tell us more about that. What is it, how did it come about, and when will it come out? 

Women's Work is a 'zine I co-curated with illustrator Celine Loup. It's a celebration of women in STEM careers, mostly currently working, in the form of portraits by contemporary female illustrators alongside bios. It also contains an interview with myself, Celine, and a number of other female illustrators (Anita Kunz, Jaleen Grove, Alice Meichi Li, and Sarah Green) that was published on Ravishly.com about the issue I'm about to discuss. The 'zine came about as a response to Nina Burleigh's cover story in NewsweekWhat Silicon Valley Thinks of Women. The cover was illustrated by a very prominent male illustrator and depicts an anonymous faceless woman in profile wearing a red dress and high heels with a mouse cursor lifting up her skirt. The illustration sparked a lot of debate online about a) why a man was hired to illustrate an article specifically about the experiences of women and, b) whether or not the visual solution itself was sexist. Many female illustrators voiced their opinions and faced hostility from our peers, both male and female, and some of us were left asking, "Well, how do we respond to this? How would we have illustrated this article?" Instead of literally reinterpreting the cover illustration, which felt like it would only spur more hostility, we decided instead to come together to celebrate the women who may be facing adversity in the tech industry, the women continuing to fight and even prosper in that environment, by having women illustrators (who sometimes face the same struggles in our own industry) draw their portraits and tell their story. I just ordered it from the printers yesterday, so hopefully it will be available soon!!

What else are you working on these days? What are you looking forward to most this year, professionally or personally or both?

I'm really excited to start teaching. It's inspiring to see all the different solutions students come up with in response to an assignment, it kind of opens your mind a bit. It's so easy to get trapped inside your own head. I'm also looking forward to moving into a studio with some other very talented illustrators, it will be nice to leave my apartment once in a while, though I'm sure the cat will miss me. I'm hoping it will help me to make some more self-motivated work, make some more products (I've been working on a line of screen-printed bandanas) and get a proper online shop together eventually. I'm also getting married in October, so there's that!