Career & Finance

Letterer and Type Designer Jessica Hische

Jessica Hische takes lettering, illustrating, and type design to a whole new level with her fun, bold designs. She has a portfolio that includes greeting cards for Papyrus, book covers for publishing house Penguin Books, and print advertisements for Starbucks; Jessica has certainly found her niche in the graphic design world. She has also been voted one of Forbes Magazine “30 under 30” in art and design, one of 25 Emerging Artists by STEP Magazine, and a “Person to Watch” by GDUSA.

It was in 2009 after many all-nighters and hand drawn designs that Jessica took the leap to strike out on her own. During this time of uncertainty and wayward scheduling, she started the Daily Drop Cap as a way to keep creativity flowing—she showcases a new hand-drawn illustrative letter every day. And even with the new influx of freelance clients, Jessica stayed true to the Daily Drop Cap and drew her way through the alphabet 12 times; by the 13th round, she asked guest designers to contribute their talent. The letters are available as free downloads to use on blogs and websites—a brilliant marketing move if you ask us! Clearly, Jessica knows her way around both the creative and business side of a successful freelance career.  

Today Jessica splits her time between Brooklyn and San Francisco (where she now calls home). And to top it all off, it’s where she set up a collaborative studio and workshop space for other creatives to utilize, learn, and grow. Jessica is a self-proclaimed “serious over-sharer” and lucky for us, she shared quite a bit about her start in design, growing into her career, and becoming an expert in her industry. And we absolutely agree with Jessica when she told us, “Everyone is different, and just when you think you figured it out you find some better way of doing things. The key is to always keep trying to be better.” Yes! 

Full name: Jessica Hische
Age: 30
Current title/company: Letterer and Type Designer
Education: BFA in Graphic and Interactive Design, Tyler School of Art, Temple University

Your first job after college was a freelance designer for a small studio in Philadelphia. How did you land this position and what did you learn?
When I was still in college, I asked my professors Paul Kepple and Jude Buffum if Headcase Design (Paul’s Studio) was hiring internships. They had never had an intern before, and after a bit of convincing they hired me. When I graduated, the studio was slammed with bookwork and it was only natural that I stay on to help as a freelancer. I ended up freelancing full-time for about six months and part-time for a bit after that. I learned SO MUCH while working at Headcase—a lot about how book projects are managed, but mostly about how much I loved illustration and that I wanted to figure out ways to do more of it. 

Due to untimely circumstances, the studio unfortunately cut your hours. But, ultimately, this led you to a job with one of your heroes! Tell us how you ended up working alongside one of your idols and how you overcame this career obstacle.
When the studio cut my hours, I was disappointed but ultimately saw it as an opportunity to do more freelance editorial illustration and design. I also picked up a teaching gig at Philadelphia University. Philly is a pretty inexpensive city (especially at the time), so it’s a bit of a freelancer’s paradise. I put together a promo to send to magazines and agencies that might hire me for illustration work, but I also sent it to a couple of my idols, including Louise Fili. When Louise emailed about coming in for an interview, I was shocked—in no way did I think that my little promo might turn into a job offer. I hadn’t planned on packing up my bags and moving to NYC for a full-time gig, but it was an amazing opportunity and I couldn’t resist!

Next up, you decided to strike out on your own with a project that earned you the moniker “That Drop Cap Girl.” Tell us about it! What gave you the courage to start your own business?
Starting my own business was a bit of a no-brainer when I did it. I had been freelancing alongside my full-time job and found out after a year or so of doing it that I was actually making more money freelancing than I was at my day job! I was learning so much from Louise, though, that it took a while to feel ready to leave. I waited until I had about six months of expenses saved before I went out on my own so I wouldn’t feel stressed over how to pay my bills. I started Daily Drop Cap because I wanted to make sure I was still lettering every day once I was full-time freelance (you never know what clients are going to hire you for, and sometimes your portfolio can get away from you). I also liked that the project imposed structure in my newly formless schedule. 

Your clients now include American Express, Wes Anderson, and The New York Times. When you started your business, how did you gain exposure for your brand? When did you finally feel like you had “made it” and that your business was a success?
Honestly, I first felt like I made it when I got my very first freelance gig from a non-friend when I was 21 years old. It wasn’t for a crazy big agency, or well-known company, but it felt like I had won the lottery. Everything grew organically—I started getting work from small regional magazines, then eventually was hired by bigger national magazines. Eventually I started getting hired to do book covers (mostly for lesser-known authors) but eventually was able to work for some bigger names. It just slowly grew over a few years, punctuated every now and then by an impressive name like AMEX until suddenly I found there were more major names than not. When you freelance, you always worry about whether or not your business will last, and I think it took three or four years of consistent end-of-year numbers to realize that I’d actually created a successful business. 

You are a letterer, illustrator, and graphic designer. We want to hear about your inspiration as a creative! Where does your inspiration come from? Do you seek it out? How would you describe your design style?
I find inspiration everywhere, but mostly from people! I do a lot of public speaking, and I always feel the most inspired when returning from a conference because of all of the wonderful people I meet (speakers and attendees alike). Personally, I find that a good balance between social time and work time is what keeps my creative engines running smoothly—that if I don’t spend enough time with people I start feeling unmotivated and sluggish. As far as influences though (which is probably what you’re asking) I get a lot of project inspiration from the content of the project itself (for instance, reading the book I’m doing the cover for gives me more conceptual and visual inspiration than spending a day in a rare books library). I do love visiting print studios though, perusing Pinterest, visiting amazing places like Letterform Archive in San Francisco. 

And now some advice! Freelancers are abundant in the graphic design and illustration industry. What guidance do you have for freelancers wanting to create exceptional and distinct work?
I guess my top advice is to try to not follow trends too closely (if you can). Dribbble and Behance can be great for getting your name out there and seeing what others are up to but if you spend too much time looking at your contemporaries’ work you run the risk of making work similar to the herd. Spend time falling in love with things that aren’t design, and let those things influence your work. Inspiration comes from everywhere and all good designers talk about how much they’re inspired by architecture, fine art, books, nature, etc. 

Just when you think you figured it out you find some better way of doing things. The key is to always keep trying to be better.

In your opinion, what traits are necessary to become a successful freelance designer? Share tips on how to be your own boss, manage your schedule, and handle payment or compensation. Some of which can be a tricky part of the business!
Every person is different, but the key ingredient is to be self-aware and to constantly evaluate your process. If there are things that you are downright terrible at, is there a way to delegate that responsibility to someone else? I’m terrible at keeping track of paperwork, so I’ve had an artist rep for years to handle that for me. As far as schedule managing, it can take a bit to understand how long projects take you to complete (or stages of projects). I live and die by my calendar, and have separate calendars for every kind of deadline, event, etc. (Finals, Sketches, Meetings, Life Stuff, Travel, etc.). I also use lists a lot to organize incoming requests / collaborations so they don’t fester in my inbox (like having a list for speaking requests so that I can go over them all at once instead of on a case by case basis). Everyone is different, and just when you think you figured it out you find some better way of doing things. The key is to always keep trying to be better. 

You split your time between Brooklyn and San Francisco, and also travel across the country for speaking engagements. Describe a typical day (or week!) in the life of Jessica Hische. Give us a glimpse into the madness!
Most months I have at least one speaking engagement, but my travel can definitely get out of hand in the fall, during “conference season.” It’s rare that I get an entire uninterrupted work week in my office during the busy times! I can’t really work on client stuff when I’m traveling for conferences because travel is so exhausting, you’re always in different time zones, and because there are always a lot of random commitments during the conference that you didn’t account for until you arrive (social events, interviews, school visits, etc.). When I’m in my office in either SF or Brooklyn, I keep a pretty regular schedule. I generally work from 9am-7pm, start my day off with an hour of email, and spend the rest of the day trying to ignore my inbox and actually get work done. My mornings are usually for sketching or brainstorming and my afternoons are spent doing vector drawing. I reserve Mondays for “admin days” so I can answer interviews, really dig through my inbox, send files to people, etc. It’s definitely tough to stay on top of everything, but since I’m in charge of how much work I take on I just tend to slow the flow of work when I’m feeling overwhelmed or have too much travel on my calendar. 

 As a business owner, how do you achieve a work/life balance?
It’s definitely tough! Work/life balance is different for everyone though. Right now I don’t feel like I have the best work/life balance because I feel stuck within a “day job” schedule because my husband and everyone around me has that kind of schedule. Generally I’m happiest when I can work when I want and play when I want, which means that sometimes I take afternoons off and work until late or sometimes I wake up at 5am to work so I can have an easier late day and evening. Having to confine myself to work within certain hours has definitely been a challenge, but I know it’s just prepping me for other life stages!


I think since people feel that they “know” me more than other folks, I’m more likely to be hired. Being myself online has helped with that. 

You admit to being an over-sharer. Us too! How has social media affected your career success?
It’s been incredibly important to my career, mostly because I think since people feel that they “know” me more than other folks, I’m more likely to be hired. If you had to look at five similar portfolios and pick someone to hire, you’d probably pick the person that you already get a sense of who they are and how they’d be to work with. Being myself online has helped with that. My following has grown really organically and it feels good to know that the people that pay attention to my work are real people and not a bunch of Internet robots. 

Best moment of your career so far?
Seeing my name come on the screen at the end of Moonrise Kingdom and all of my friends clapping and cheering!

In five years, where do you see yourself and your business?
I have no idea. I’m not a five year plan kind of person. I could potentially see myself having employees at some point, but I’m not sure if that’s a five year or 10 year plan. I tend to let my career and work grow organically in the directions that my interests take it. I’ll undoubtedly still being doing lettering, but I might end up doing more type design. I might focus more on brand refreshes, who knows! It really depends on the experiences I have, the kind of clients that come my way, and all sorts of extra factors like where we’ll be living, kids, etc. 

What advice would you give your 23-year-old self?
No matter how motivated you are, still find time for friends and family! I definitely let a few relationships get pushed aside when I was struggling to get my career going early on. 

Jessica Hische is The Everygirl…

Morning or night?

Best advice you’ve received?
“Don’t do anything you wouldn’t want to see on the front page of The New York Times.”

If you could have lunch with any woman, who would it be? What would you order?
Tina Fey or Amy Poehler (or both!) and I would order a pulled pork sandwich. 

Who would play you in the movie of your life?
Hard to say! I’ve (at different times in my life) been told I look like Jennifer Aniston and Mandy Moore, but I’m not sure if they’d be my top picks.

Aidan or Big?
Aidan for sure, though it’s been so long since I watched that show (and I was only a sometimes watcher) so I might have to re-evaluate.