Illustration by Ruby A. Photograph by Peter O’Dwyer.

If you are a young and aspiring designer (me) with a particular affinity for typography (me again) who dreams of working with the likes of Wes Anderson and Louise Fili (guess who?), you might catch yourself looking at graphic designer and illustrator Jessica Hische and thinking, WHY CAN’T I BE YOU? At the age of 28, Jessica has a remarkably prolific career; she is known for her gorgeously elaborate custom lettering and illustration for clients like Target, Barnes & Noble Classics, and National Public Radio. Jessica is a Big Deal not only because of her professional awards and achievements, which include being named an ACD Young Gun and a Forbes 30 Under 30 in Art & Design, but also for her popular web-based side projects, like her brilliant Daily Drop Cap project, launched in 2009, where she created a different illustrated capital letter every day, going through the alphabet 12 times (which is lovably nuts). She’s a frequent contributor to the oft-inspiring Friends of Type blog, and her wedding invitation is the loveliest thing on the internet. I sat down with her and half a dozen mini cupcakes at her studio, Title Case, in San Francisco, to pick her brain.

Jessica, thank you for being so generous with your time! Once I discovered how to activate the Teen Girl mode on your website,* I knew you were one of us, and we really had to talk. So tell us: what is it, exactly, that you love about what you do?

I love almost everything about what I do. I get paid to draw all day, I get to read and respond to wonderful emails from aspiring designers, illustrators, and letterers and help them in any way I can, and I get to travel around the world talking at conferences and meeting people whose work I admire. I’m definitely a lucky girl, and every now and then I have to step away and remind myself just how lucky I am.

You created the film titles for Moonrise Kingdom. What was it like to work with Wes Anderson?

It was a dream, because Wes had his hand in every aspect of the visual process. I would get emails at 2 AM asking to make the R slightly smaller, or to make something else a little bit rounder. I didn’t expect that attention to detail.

Jessica’s lettering for Moonrise Kingdom.

What is your stance on attending design school—is it necessary for the type of work that you do?

I think attending art school is an awesome and wonderful experience whether or not you know for sure if you want to be a fine artist. College in general is really just a wonderful way to transition into adulthood, as long as you don’t treat it like a massive excuse to party and drink your brain cells away. I worked incredibly hard in school, and because of that my professors gave me opportunities that other students didn’t have. School is what you make of it, and you could go to any college and get a great education as long as there are a couple of professors there who are willing to put the time in and that you, in turn, are willing to give 110%. There are people out there that say college isn’t necessary, but I definitely wasn’t mature enough to enter the workforce at 18, and I feel like I really found myself in art school. Plus, there are very few other opportunities to be surrounded by so many like-minded people having intense discussions about your work. I miss art school like crazy because those kind of critiques are hard to come by, and no matter how many artsy friends I have, nothing compares to being surrounded by 100 peers, all working 24 hours a day, exhausted but excited.

What advice do you have about getting internships, making connections, and getting your foot in the door? Also, please tell us how you got my dream job working with Louise Fili!

For anyone out there looking for an internship, the best advice I can give is: meet with everyone in person if possible. You’re far more likely to be hired if people get to know you a bit, and I’ve definitely come across a number of young designers that I would probably hire before even looking at their portfolio just because I think they’d be fun to have around the office, and they have the right attitude about learning and working for someone else. You might be the most talented person out there, but if you’re not pleasant to be around or have an ego bigger than Michigan, you will have a much harder time finding a really excellent job with someone willing to mentor you.

I ended up working for Louise almost by accident—I was a huge admirer of her work, and so I sent her a little gift in the mail. I didn’t expect anything in return, I just wanted to show her some of what I was making and tell her how much I loved her work. She called me up for a portfolio review and that day offered me a job. It completely floored me that reaching out to someone personally could make such a difference, and that you didn’t necessarily have to send over a résumé and cover letter to get someone to peek through your portfolio.

Jessica’s entirely new font, Buttermilk.

You grew up in a small town in Pennsylvania. We get comments from Rookies all the time saying, “My town is so boring—what do I do?” How did you beat boredom and keep yourself creatively satisfied?

I think the biggest challenge anyone from a small town has to face is how to defeat small-mindedness and not get caught up in the drama that can happen in an insular community. Once I was able to gain perspective and feel more connected with the world through traveling and by attending a university fairly far from home, it was a lot easier to overcome any obstacles that might have existed before. But I’ve always loved to make art, and I think I would have pursued it whether I came from a small town or a big city. I’m happy that I’ve had the opportunities to avoid being a big fish in a very small pond.

You’ve certainly expanded your pond, from having spent most of your professional life up to now between Brooklyn and San Francisco. I’m curious if you’ve observed any major differences in the professional and social environments of the two coasts.

The main difference I’ve seen in San Francisco is, because the community is smaller and more tech-focused, people are incredibly hungry for more design events, workshops, and community-related activities. In New York, there is always so much going on that by starting up another event you don’t feel like you’re making a huge difference, but in San Francisco you do. I think it’s a great place for me to be for now. I miss Brooklyn terribly, but I love all the people I’ve met in San Francisco, and I definitely love my studio situation here so much.

Your studio is kind of amazing. You work independently, in your own office, which you share with another designer. What kind of person succeeds and enjoys this type of work situation?

I think people that have the most success in any career are those that can remain a bit humble—or at least empathetic—no matter what their career status. If you love people—love interacting with them, working with them—you’ll have success in your career. To have success as an independent designer or creative type, you have to be driven, you have to at least try to be organized, and you have to be pleasant to work with. Art directors will come back to you over and over again if you make the experience of working together a pleasant one. If you ask them, they will tell you that the number-one thing that turns them off from working with a person again is if that person was disrespectful, unkind, or seemed “above” the project. Freelancing is all about forming short partnerships with art directors and clients and making them feel that you’re as excited about it as they are.

A day planner designed by Jessica with full-page typographical illustrations.

So many creative people I meet—fellow students, design teachers, work colleagues—have a hard time saying no to projects, and get overwhelmed by committing too much. I love your “Should I Work for Free?” flow chart, because sometimes it’s OK to take a break from saying yes! Do you have any advice for the chronically nice?

It’s OK to do work for free if it’s for a cause you believe in, but know when you’re being taken advantage of and when you’re not. I think one of the best ways to work for free or cheap is to actually invoice the client for what they should be paying, and then outline the discount that you’re giving them for whatever reason, like “I love what your non-profit does!” And let them know that if they come back to you for more work, the same discount might not apply. In this way, they treat you as if they’ve hired you as an expensive designer, with respect and as a partner, even if they aren’t actually paying you like one. This also prevents you from doing cheap work for them or others forever.

Also, forgive yourself for occasionally doing free work just because you want to, as long as you don’t think that doing so will injure others in your industry. If a giant corporation asks you to do something for free, and you accept it, you’re actually helping to devalue ALL designers’ work, but if a friend asks you to design an album cover for free, you’re just doing a favor for a friend. There is definitely a distinction.

How much time and devotion did it take to be as accomplished as you are at such a young age? I’m planning on never sleeping during my 20s, and I wonder if I will make it out alive.

I think most people that have a lot of success early in their careers don’t see what they do as “work”—I would make art whether or not anyone was paying me to do it. If you can see your career as your calling more than your job, it’s easy to devote your life to it. There is a very blurry line between “life” and “work” for me, and because of that I’ve been able to put a lot of time into it, but I love every minute of it. It’s easier to put more hours in when you’re young, so why not be a little sleep-deprived if you’re excited about everything you’re making? It’s been a little harder to find work/life balance now that I’m in my late 20s, mostly because there is a definite difference in how much your body can handle as a 22-year-old versus as a 28-year-old. It’s only a few years, but I have to make sure that no matter how hard I’m working, I’m not letting my work get in the way of my health. I definitely had a few unhealthy years in my early 20s, but I wouldn’t take them back now. I loved working long hours, and throwing myself headfirst into projects. Just do what you feel capable of doing. You can work hard and get a lot done without getting yourself hospitalized. ♦

* See the heart in the upper right-hand corner of Go ahead, click it!