This week we had the pleasure of speaking with lettering bad-ass Jessica Hische. Jessica has been working on her own as a letterer, illustrator, type designer, and relentless procrastiworker since 2009 and has worked for (and continues to work for) a lot of wonderful clients like Wes Anderson and Penguin Books. In September of 2015 she published her first book In Progress: See Inside a Lettering Artist's Sketchbook and Process, from Pencil to Vector. When she's not manipulating beziers or working on fun projects in San Francisco, you can find her at the airport en route to a speaking engagement. To top it all off she welcomed her daughter Ramona Mae into the world last April! We so enjoyed chatting with her about how she balances life and work and continues to make time to create for the love of it.
Hello Jessica, thank you for taking the time to answer my questions! Can you tell us a little bit about your path to becoming a freelance lettering artist?
Sure! My dream of being freelance started when I lived in Philadelphia and was surrounded by freelance illustrators. I really loved how their work lives and personal lives seemed incredibly intertwined. I starting sending out promos and picking up freelance clients, then moved to New York to work for Louise Fili full time (pursuing my freelance dreams at night). It was under Louise's tutelage that my love of lettering really flourished, and it was during that time that my freelance career began to pick up. Eventually, it made financial sense to leave my day job (as emotionally hard as it was to branch out on my own and away from my mentor). At the time, my freelance work was mostly illustration, but as I incorporated lettering more and more into my illustration work, clients began calling for just lettering. I worked really hard, stayed involved in the creative community (both in person in NYC and online), and created passion projects in my free time that helped me find an audience (or really helped an audience find me).
In the beginning, how did you attract your first good clients?
I worked with an artist rep from very early on, and he was great at putting my work in front of creative directors and art buyers. Above all though, I think most of my best projects came from referrals, either from past clients or people who had met me through the creative community.
You are a relatively new mom to your beautiful daughter Ramona. How has becoming a mom changed how you work and/or the types of projects you take on?
It's definitely made me a more disciplined worker—I can't let myself screw around during the work day anymore because I know I can make up the time at night or on the weekend. Work/Life Balance used to mean working whenever I wanted to and living somewhere in those hours too—now it means making sure I devote my full self to work in the hours that I'm at my office so I can devote myself fully to my daughter when I'm at home. There have been some definite roadblocks—I find myself taking on "safer" work or being afraid to say yes to very ambitious projects (which would potentially require a lot of last minute late nights or weekend work), and saying yes to speaking gigs is...complicated. All in all though I have been really happy with the flexibility that a freelance career provides with transitioning to be a parent, and only get frustrated when I end up picking up a lot of our household slack because of my flexibility.
You often self-describe as a "procastiworker" now that you have a baby, do you feel that you have time to pursue self-created work?
I do! Though I have to remind myself more often that that work is "worth it". When you have less hours in your day to devote to any kind of client / creative work, you tend to judge yourself pretty harshly if that work isn't pushing you forward or directly contributing to your career. I've had to forgive myself a lot for working on things just because I felt like working on them, not because I knew they would make me money or would bring in more client work.
Since having a baby I feel like I have a much harder time remembering things and focusing, curious what your tips are for being your most productive?
Once we got through sleep training and I could get more than 2 hours of sleep at a time, things got A LOT easier. I also found that in general after I stopped breastfeeding it was a night and day difference in terms of productivity (if/when we have another baby, I'm going to stop breastfeeding a lot sooner—it was brutal to work / pump at the same time). As far as general productivity tips, my biggest tip is to try to not let menial tasks take over your life. It's very easy to spend an entire day on the phone with customer services, organizing things, poking around in email, etc. I try to do all of my weekly emailing on one day ("Admin Mondays") and only reply back to urgent emails at other times during the week.
"As far as general productivity tips, my biggest tip is to try to not let menial tasks take over your life...I try to do all of my weekly emailing on one day ("Admin Mondays") and only reply back to urgent emails at other times during the week."
What has been your greatest struggle as a freelancing mom so far?
One of the things that's been hardest for me is realizing that I can't really post photos of my daughter (publicly) online, because clients assume I'm only working part time or am still out on leave. I was getting far too many emails from potential clients that started with "I don't know if you're back at work yet but..." and for every one of those emails I know that plenty of potential clients were just not reaching out at all. I never really worked hard at promoting myself prior to having a baby (my day to day life posts did a lot of that work for me, because my life was so centered around work), but now I try to make more of an effort and when I do I feel the effects immediately. I have plenty of male friends who do not need to censor their personal lives with their kids online because no one would ever assume they were not working, and the double standard is infuriating.
You have always been a strong advocate for fair pricing and the value of creative talent, have you found as a woman that you need to work harder to explain your value?
I didn't get this feeling until relatively recently, but I do feel that clients tend to push back a little harder or balk a little louder when women ask for high sums of money on projects. I do have the problem of being "an explainer" for all things. If I turn down a project, I feel like I need to explain why. If I turn down a speaking engagement, I feel like I need to justify it with a conflict. It's something I struggle with—I should be able to ask for something or say no to something and not have to explain my motivations, because those motivations shouldn't matter if my decision is final.
"I should be able to ask for something or say no to something and not have to explain my motivations, because those motivations shouldn't matter if my decision is final."
As you know well, freelancers are just as much small business owners as we are creatives, what are three tips for managing the nitty-gritty components of your business?
Hire people to do the things that you're bad at.