Years ago, our host invited Jessica Hische to come and speak at the first Women In Design event and she blew everyone away with her humor, honest vulnerability, and passion for her work. Jessica is a lecturer, illustrator, and type designer — hands down one of the most important designers living amongst us in our generation today. Her clients include Wes Anderson, Dave Eggers, Penguin Books, The New York Times, Tiffany & Co., the list goes on and on.
She recently released her book, In Progress, where she shares her creative process, how her career unfolded, and how each opportunity leads to the next. We only scratched the surface in her interview, but we still managed to cover a lot of juicy stuff, plus wisdom and tips for the striving creative.
Forgive yourself for decisions you made that were best for you at the time.
— Jessica Hische
Majo: Let’s talk about how you landed that job, because it’s really interesting.
Jessica: It was really random. This happens to a lot of people when they’re dating. You put your “I’m fine with myself, I don’t need someone” energy into the world, and of course that’s when everybody is falling at your feet and coming to your door. That was sort of the energy I was putting out at the time. I was like, “You know what, this is my time. I’m going to work on my freelance illustration, I’m gonna be like all these people I know in Philadelphia that have their shit together and their lives seem great. I’m going to be a freelance illustrator. Life is sweet and everything’s amazing.”
So I put together this promo to get freelance illustration work. This was a huge deal for me because I was totally broke, you know, I was fresh out of college, trying to pay down my student loans, living with three people. And I made this holiday promo, which was The 12 Days of Christmas, and made it into a twelve postcard set with a belly band and put them in a little envelope. The whole project cost me $1,800, which was…
Jessica: It was basically a billion dollars to me at the time. I think it was more than what I sold my car for.
Majo: So wait, I want to understand your motivation for this. What I’m understanding is you were doing this out of a sense of…
Jessica: A sense of, “I’m going to get illustration work! And it’s gonna be great.” When I graduated college, all the designers left. There’s just not a lot of design jobs in Philadelphia. So the few people who did get those jobs stayed, and then everyone else went to New York or LA or their hometown. Philadelphia is a freelancer’s heaven because there are still ways to live somewhat cheaply. And so a lot of the creative folks I was meeting who were still around were freelance illustrators. And it was through seeing their lives that I was like, “Oh my god, I think I just wanted to be an illustrator this whole time, I think this is what I’m supposed to be doing!” And I still think that because lettering is essentially illustration.
Majo: Of course.
Jessica: So I made friends with this rep, because all my friends in Philadelphia were repped by this guy, Frank Sturges, he’s still my rep now. But he wanted to redo his website and some friends had recommended me to help him with the design, and while we were doing that I told him I wanted to be an illustrator. And he was like, “I don’t know man, you’re pretty green.” But then I put together this promo of The 12 Days of Christmas, and when he saw the work he was like, “Oh wait, you’ve nailed something here,” because I had found a style that was a little bit more unique. And he said, “I’m going to give you a list of people to send this to, and hopefully that works out.”
So he gave me this list of like two hundred and something art directors at ad agencies and magazines, and as I was putting it together I decided I also wanted to send my promo to a couple people that I just wanted to have one. So I picked a few design heroes, found their addresses, and was just sending it out as a gift without expecting anything in return. It was around the holidays. And one of the people I sent it to was Louise Fili, who had been such a hero in college and all my professors had been obsessed with her. And I heard nothing back, except from Louise.
She reached out and invited me to do a portfolio review with her. So I went up there and showed her my stuff, which I was really proud of at the time, and at the end of the review she was like, “I think this is great, I’m trying to fill a position in my office. Would you be interested?”
- Growing up as a quiet art kid from a small town. [4:08]
- On Jessica’s work ethic, the awkwardness of high school, and her book, In Progress. [10:13]
- How her parents’ divorce made her a kinder person, and why “oversharing” is a huge part of who Jessica is. [14:53]
- The shock of criticism: Being told she wasn’t “good enough” and how she responded. [20:16]
- Dealing with competition in art school, doing lots of internships, plus a great pro tip for students. [26:30]
- Going all in: The illustration promo she put together to get noticed, and how it paid off. [31:44]
- On working insane hours, being upfront with her boss about what was important to her, and how hard it was to quit. [42:16]
- Diving into freelancing full-time and being her own boss: How Jessica dealt with doubt and her biggest fear. [50:24]
- Why Jessica likes to think of her life and career as a constellation, plus some great advice for creatives looking to attract business. [54:20]
- The importance of being an accessible creative leader, speaking her truth, and maintaining humility without losing self-confidence. [1:01:08]
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