Jessica Hische

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.

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Becca Clason

Becca Clason is a northern Utah-based freelance lettering artist and stop-motion animator. After studying advertising and graphic design at Brigham Young University, she began working as an advertising art director in New York before transitioning to full-time freelance in 2015. Her clients include Disney, Target, American Express, Kellogg's Special K, The Washington Post, Denny's, Annie's Homegrown, L'Oréal, Sabra Dipping Co., General Mills' Lärabar, and more.

Tell me about your path to becoming a freelance designer and letterer.

I started lettering casually in college, without really knowing that it was “lettering”, and I didn’t find out that lettering had a name and was a profession until a few years after I graduated from college. I fell in love immediately and knew it was what I wanted to do for the rest of my life. I wanted to become great at it, so I practiced all the time. I studied calligraphy on my own, always had a sketchbook with me, did online classes, and attended various workshops. I’ve gotten a lot better over the years, but there’s still so much to learn, and I don’t ever want to stop learning and pushing myself.
I worked full-time doing graphic design for eight years before I became a full-time freelancer. A lot of people think freelancing full time is something they can jump into right away, and maybe for some people that’s the case, but for me it took several years to build my skills, portfolio, and client list to a point where I was able to jump off and expect to pay my bills through freelancing. I worked on the side as a freelancer for about five years, and throughout that time I continued to practice lettering, hone my craft, and build better client relationship skills and business skills.

A video posted by Becca Clason (@beccaclason) on

In the beginning, how did you attract your first good clients?

Instagram has been a huge help for my career. I started getting into tactile typography the summer of 2012, and quickly became enamored with it. I loved being away from my computer and working by hand. So for fun and as a creative outlet, I started creating hand-lettered designs using products, food, or flowers, and posting them to Instagram, and people really seemed to enjoy my posts. I slowly started gaining a larger and larger Instagram following, and among those followers are social media managers for brands, art directors or creative directors at ad agencies and magazines, which has led to some great projects I’ve been able to work on with clients.

Do you have any tips for being your most productive?

If I don’t exercise and take a shower first thing every morning, the rest of the day I feel like I’m running behind and am off my game. I like to start the day on a healthy note that makes me feel good about myself for the rest of the day. Also, I focus better in the morning, so if I can get started on my work at a regular time in the morning, I’m always more productive.

What has been your greatest struggle as a freelancer so far?

Not knowing when the next project is going to come is the biggest struggle with being a freelancer. Sometimes I’ll go a couple weeks without any client projects to work on, and other times I have to decline projects, because I have too much on my plate. There are some months I might not make very much but other months that I make enough for three months. I’d much rather be doing what I’m doing than working in an office from 8–5, commuting, and getting a steady paycheck. So there’s more worry about making enough money during the slow times, but the benefits of being a freelancer greatly outweigh the worries.
During my slower times, I’m able to focus on my brand and portfolio by creating personal lettering designs and stop-motion animations using products and styles that I have been wanting to explore. Then I post the work online, which keeps me relevant and continues to get people looking at my work and thinking about hiring me for future projects.

What is your favorite thing about freelancing?

There are several things that I love about freelancing. I get to work on projects that I love. I never wish I were at home working on something else, which is what used to happen when I worked at an office, because now I get to do that “something else” from home every day. I love that I can work from anywhere, because my husband and I recently bought a cabin in the mountains of Northern Utah and moved there in November. I love that I have a flexible schedule, which is extremely important to me now since I’ll be having a baby in a couple of weeks.

"I never wish I were at home working on something else, which is what used to happen when I worked at an office, because now I get to do that 'something else' from home every day."

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You are represented by several agents, can you describe a bit about the process of hiring an agent?

Definitely, although it’s more like you hire each other. I don’t really work for my agents, and they don’t really work for me. It’s more like a partnership.
When I first decided I wanted to seek out representation, I did a lot of online searching to find different agencies who represent typographers, artists, and illustrators. I sent out personal emails to each one giving a brief explanation of what type of work I create, letting them know I was interested in being represented by them, attaching a few samples of my work, and including a link to view more of my work. It doesn’t always work out that you’ll find a good fit on your first try. I didn’t sign with anyone the first time I emailed some agents, but after five or six months of working on my portfolio and creating new work, I emailed them again (some the same, some new), and this time there were a couple of places who wanted to represent me. I signed with Snyder New York to represent me in North America, and I couldn’t love working with them any more.
Since then, some agencies in different areas of the world reached out to me to see if I wanted to be represented by them. So artist reps are always looking for good people to represent just the same as artists are looking for agents to represent them.

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Do you have any tips for dealing with the nitty-gritty business details?

Luckily, my agents take care of most of the nitty-gritty business stuff! What a relief. They deal with all the contracts with clients, paperwork, and invoicing the clients. I invoice my agents once the project is completed, and I get paid once the client pays my agent.
I do have to save all my invoices for tax purposes, and since taxes aren’t taken out of my payments, I set aside ⅓ of all of my payments for taxes in a separate bank account, so when it comes time to pay taxes, I have all the money there.  

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Take breaks! Sometimes there are days when I don’t leave the house, but whenever I take a break to go on a drive or a hike with my husband, I am so glad I did. I need refreshers without realizing I need refreshers, but it’s good for the mind and soul if I spend time outside every day.
Get off your computer at night. Sometimes if my husband and I are watching some shows after dinner, I keep my computer on my lap, editing some images from my photo shoots or responding to emails. I feel like I need to be productive all the time, but that’s counterintuitive, because if I don’t stop working at a good time every day, I’ll just get burned out.
If I have a deadline and need to finish putting together an animation or editing a design, that’s another story. I’ll stay up all night if I have to. Haha.

The 3 greatest attributes you need to be a freelance creative are:

Drive, good will, and time management (and I’d like to add a fourth: brand strategy).

Becca just gave birth to a beautiful baby boy named Ira! Send her love by getting social with her in the links below!

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