Award-Winning Cartoonist And Author Jessica Hagy On The Creative Life and "The Art of War" As Metaphor For Hassles Big And Small

 In Culture

Webby-winning cartoonist and author Jessica Hagy is known for her insightful, humorous and beautifully simple illustrations that translate complex concepts into entertaining and accessible nuggets of wisdom. Her Webby award-winning blog, Indexed, explores business concepts ranging from ego to optimism–all on 4″x6″ index cards, posted every weekday morning. Her book “How To Be Interesting” (2013), charms and inspires with illustrated advice in a similar vein to Austin Kleon’s “Steal Like An Artist,” and “Show Your Work.”


Hagy brings her skillful brushstroke to bear on her latest project, “The Art of War Visualized.” Originally published in installments on, the project is a visual translation of Sun Tsu’s classic text for the Information Age, bringing to life the Chinese general’s 2500-year-old text with ink brush diagrams and bold typography.

While “The Art of War” has served as required reading in business classes across the world for decades, Hagy’s re-imagining of it makes it even more relevant to today’s entrepreneurs,  creative professionals, corporate warriors and students. We caught up with Hagy to discuss her new book and how “The Art of War” applies to the creative life.

Kelly Hamilton: What made you decide to take on “The Art of War” as your next creative project?

Jessica Hagy: We have a big bookshelf filled with all sorts of books in our basement, and I was just looking through what we had and we had three copies of “The Art of War” and I realized I had never read it. When I picked it up and started thumbing through it, I noticed it’s written in really short, little verses. Almost like the Bible, everything’s numbered and it’s really concise. I was like, ‘I can illustrate this and use each verse as sort of a caption for the image.’ Then I just set it out like, ‘Okay, if I do one chapter every two days and just get this done, we’ll get it done in like, six weeks.’ It was really satisfying and the concept was a lot more interesting and artful and thoughtful than I been expecting it to be. I thought it would be really violet and bloody,  like ‘This is how you stab a guy in the eye’. It wasn’t at all. It was really, really, really thoughtful and strategic and more zen than I thought it would be.


Kelly Hamilton: That’s what I got out of it. It is about how you can approach “battle” but from this very philosophical, metaphorical, standpoint. I hadn’t yet sat down to read “The Art of War” before–though I always felt I should–and reading it in your format allowed it to be much more accessible.

Jessica Hagy: The word “metaphorical” is so true because battle is sort of a stand-in idea for problem solving and getting through anything. It doesn’t have to be all-out violence or life or death situations. It’s applicable to every little hassle.


Kelly Hamilton: Your first illustration project was actually a blog you created in 2006, “Indexed,” where you still post an illustration every weekday morning. What was the inspiration for that?

Jessica Hagy: Back when I was working in Columbus, Ohio, I was at Victoria’s Secret Pink when that brand was launching. Do you remember when Pink was on the back of all the butts, like Juicy Couture was really big? I was in the middle of that and I was writing all sorts of things for Pink and I was going to school at night for my MBA. At school I was doing all these concepts for people who were really free with information and they were like, ‘You should know this and this and this. And this is how this works and this is what this looks like.’ Then I would go into work and they’d be like, ‘We need to sell five for twenty-five underwear, can you do that this week?’ and I was like, ‘Oh, my brain.’

I had read somewhere that every writer needs a blog so I was like, ‘I’m going to put up a blog” but I didn’t want to do a typical one like, ‘This is what my breakfast was’ or ‘This is what I’m thinking about.’ So I just started, basically stealing office supplies and drawing little graph things and I didn’t think anybody would find it but they did, and it became sort this weird internet thing. Now it’s just part of what I do.

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Kelly Hamilton: You started it in 2006, so that pretty much makes you a pioneer in the blogging space, don’t you think?

Jessica Hagy: In 2006, everybody was just like, ‘Oh, you need to have a blog.’It was just what you did at the time. I started the site on Blogspot so it was a free service. I had no HTML skills. I just threw it up there. The fact that I still do it, people are like, ‘Wait, what?’ Because everything has moved so differently online and there are so many different social channels, it’s like, ‘Those should be on Tumblr and you should have a Twitter feed and you should have a Facebook page.’ I have all of those things now but everything still comes out of the old school 2006 blog.

Kelly Hamilton: I think a lot of blogs were started back then that just went away. People gave up on their ideas and it seems like you just really stuck with it and it’s probably continued to build and maintain as a platform. It’s pretty amazing. Is there anything that you think made you stick to yours while others might have faded as ideas that didn’t resonate as much with people?

Jessica Hagy: I think a lot of times, when you have something creative and you don’t get any feedback for it or it’s just sort of withering, you start to doubt, ‘What is the point of this and should I really keep going?’ I think that’s a personal question for everybody. I don’t think you need thousands of people every day commenting on something for it to be a satisfying experience. Even if four people read and those are the most important four people in your life, that’s probably enough to keep something going.

Kelly Hamilton: How did the practice of posting something every day for “Indexed” inform your approach to “The Art of War” project?

Jessica Hagy: I’ve been practicing that sort of format for a while–a billion years in Internet time. I’ve gotten to the point where it’s almost second nature. Sitting down and thinking about a concept and how it works in the graph for and how that translates has really become less of a struggle and a challenge and more of like, ‘Okay, how can I play with this and how can I play with it even more?’ In that case, I’ve been able to sort of make this little language my own thing. It’s become a lot more, instead of a, ‘Oh god, what am I going to do today?’ it’s more like, ‘Oh, I’m done with seventeen ideas, which one should I use?’



Kelly Hamilton: Do you have any advice you like to give maybe, younger or aspiring professional illustrators or artists?

Jessica Hagy: One of my very first interviews I had, I was still in college and I was looking for a job as a copywriter and I had on top of my resume my name and I wrote, ‘aspiring copywriter’. The creative director that I ended up working for said, ‘No, you’re not aspiring. You are what you are. Don’t say you’re aspiring to do anything, just start doing it.’ That’s how anybody gets anything done. You’re not trying to be an artist, you just are an artist. You’re not trying to be something, you just are that something. I think people getting just a little bit of confidence that you can take the word aspiring off your resume, it really is a bigger mental jump than you think. That was a really valuable piece of information and advice that I got.

Kelly Hamilton: That is great advice, I love that. You have to show up and also own your identity and doing that will probably bolster you, even though you feel like you might be an impostor at first.

Jessica Hagy: I still feel like an impostor. I still feel like someday somebody’s goinog to be like, ‘Um, what is going on here? What are you doing?’ It feels really silly. I’m just waiting for that day that somebody’s like, ‘You’re just that weird little middle-schooler who doesn’t know anything about anything. What are you trying to do? Who are you trying to trick here?’ The answer is: pretty much myself, first, and then everybody else, because that’s what most artists run into. They’re like, ‘Am I faking this? Am I the real thing?’ I think as long as you’re sort of worried about that you can just keep going because you’re not super snotty about your work yet and it’s not super precious. It’s healthier.

Join Jessica Hagy on Monday, March 30 at Maryville University Auditorium for the Maryville Women in Leadership Forum. “The Art of War” released March 10 and is available at Left Bank Books. Watch the book trailer here.




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