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Interviews

Jessica Hische: Tomorrow I’ll Be Brave

Almost everyone has a fear of failure and that emotion can feel paralyzing when it comes to both life and work. Achieving is great, but, as Jessica Hische has learned, real accomplishment is pushing through the initial fear to actually start creating.


Procrastiworking (noun): The work you do while you procrastinate is probably the work you should be doing for the rest of your life.  

If you’re in the design community, you might already be well acquainted with this word and its definition. And even if you don’t know the term, maybe you know its creator, Oakland-based lettering artist, type designer, illustrator, and author Jessica Hische.

The 34-year-old originally conceived of the word to describe the advice she was giving to young artists who were having trouble figuring out a direction. “Over the course of my career I’ve tried to pay attention to the work that I do when I’m putting off other work,” she explains on her site. Passion projects can be very telling.

Hische discovered procrastiworking for herself at Tyler School of Art in Philadelphia, when her own passion for graphic design overshadowed her lifelong interest in drawing. “I took a graphic art class and found myself procrastinating from all of my fine art work to work on my graphic design projects,” she recalls. After graduating, Hische transformed this enthusiasm into a successful illustration and lettering career.

Hische photographed in her office in California’s Bay Area.

Today, Hische’s professional projects reach across mediums and range from corporate powerhouses like Target and Tiffany & Co. to more offbeat indies like McSweeney’s and Wes Anderson’s Moonrise Kingdom.

Hische might be as well known for her beautiful hand-drawn letters as she is for her hands-on approach to sharing professional insights. Her prolific, multimedium advice includes speaking at creative conferences, workshops, seminars, and on podcasts. The artist’s first side project, Daily Drop Cap, a website she created in 2009, offered bloggers an original daily letter illustration to make their blogs more beautiful.

She drew her way around the alphabet 12 times for the daily project that effectively transformed into a massive online gallery. Her “Should I Work for Free?” flowchart, an analysis of a question every creative person faces in their career, is online and also available in a letterpress print. Don’t Fear the Internet, a site she created with her web designer husband, Russ Maschmeyer, was meant to demystify HTML for beginner web designers. “I love making things and love creating, but I’m not immune to burnout,” she says. “The work that I do to help others is just the best motivator in the world.”

In her new book, Tomorrow I’ll Be Brave, that encouragement is extended to a much younger audience. It’s an uplifting bedtime story offering children the confidence to try new things. While her first book, In Progress: See Inside a Lettering Artist’s Sketchbook and Process, from Pencil to Vector, literally walked readers through her own creative process, this one is a different kind of support guide. It recognizes that the definitions of success can be different for everyone.

But, Hische might agree, positivity and procrastiworking are good places to start.

Congratulations on Tomorrow I’ll Be Brave. This children’s book offers encouragement to keep trying even if you don’t meet your goals right away. Have there been some moments where you have learned from the process of trying and not always succeeding in the way you imagined?

This theme definitely resonates with me. I feel like it ends up being a central theme of a lot of the public speaking that I do, and a lot of the one-off mentoring sessions I end up having with people. I’m a little addicted to getting coffee with strangers and playing design therapist. Part of the reason why it resonates so much for me is that “big picture” dreams felt so far off when I was younger and still kind of do as an adult. I can feel really demotivated by the scale of big projects and big life shifts.

Achieving is great, but the real accomplishment is pushing through the initial fear to actually start doing something.

Because of that, I’ve sort of adapted to be a person who “Tarzans” through life and through their career – moving forward by grabbing the closest vine, one at a time, until you reach something close to an end goal. Your path isn’t really a straight line and your choices can push you in directions you didn’t initially plan for. I’ve met a lot of people like me – people who for one reason or another feel too intimidated to start something they perceive as being bigger than them, or feel way outside of their comfort zone.

Almost everyone has a fear of failure, and that fear can be really paralyzing when it comes to both life and work. Achieving is great, but the real accomplishment is pushing through the initial fear to actually start doing something.

Spreads from Hische’s new book Tomorrow I’ll Be Brave. Images courtesy of Jessica Hische.

Is this a lesson your own parents imparted to you as a child, and did it impact your own creative journey?

It definitely came about in my childhood, but probably through my parents trying to comfort me when I was being too hard on myself. I hold myself to a high standard and have a hard time forgiving myself when I mess up. When I was younger, I always felt that once I ruined something, the only way out was a total do-over, not just moving forward and accepting that things can’t always be perfect. I’ve abandoned dozens of sketchbooks because of one bad drawing. I’d given up on courses in school because I got one bad grade and my ability to have straight A’s was ruined.

I put so much pressure on myself that my parents’ main job was to help take the pressure off. I think a lot of kids need this – they need to be pushed to try new things, but too much pressure ruins an activity, dampens your desire to learn and try new things, and can shut you down creatively and otherwise.

Extracurricular projects can be a low-pressure way of exploring new things and even opening new doors. Did Daily Drop Cap impact your career?  

Daily Drop Cap was my first big side project. I think the biggest thing it did for me was to give me a story beyond just being another designer doing client work. It was an exercise in creativity for me, challenging me to make new things every day even when I was busy or not feeling particularly motivated. It was a way for me to give away my work by letting people use them on their blogs. It’s the reason I started getting invited to speak on stage, which I think has opened doors for me and established me as a leader in the community.

Hische lives and works in northern California.

Has there ever been a case where side projects derailed your work? Or didn’t work out the way you intended?

I wouldn’t say that any have derailed my work, but a few of my larger website projects did become a bit of a burden. Inker Linker, for example, is a site that I was really happy to make and am definitely glad that I spent the time putting together, but I never intended to be a webmaster for a printer website forever. I haven’t done anything to make money from it – the only “ads” I’ve run were link exchanges – but I have to pay someone to help me update it and approve comments.

What did you learn from them?

I think anytime you make a project, especially an app or website, you have to consider how much ongoing maintenance is required, and you need to ask yourself if that’s something you’re willing to take on.

What are the most effective ways you’ve found to make a difference?

I think when I get to personally engage with people in a one-on-one way, it ends up feeling the most significant, both for myself and I think for them. I try to write everyone back who emails me, though I can take a long while to respond, and a few times a year I get a very personal and vulnerable email from someone struggling with something in their life.

Everyone knows the phrase “Money can’t buy happiness,” but making enough money is  important in contributing to the ability to be happy.

Sometimes it’s someone trying to re-enter the workforce after having children, sometimes it’s a new designer starting out, sometimes it’s an older person trying to start a new career as a designer. When I read their stories and hear about the things they feel are holding them back, it’s very moving. I try to give as in-depth of a response as I can, giving practical advice, encouragement, and sharing resources.

I’ve had a number of people write me incredibly moving and flattering emails about how something I said or did dug them out of a very specific creative rut, or that some encouragement that I gave them years before ended up being a turning point for them pursuing a new passion.

Is there a specific example that comes to mind?

Six years ago, a man reached out to me about helping him propose to his then girlfriend – she was a huge fan of mine and they were going to be in San Francisco and he wanted to propose to her there. He wanted to commission me to make a piece of art asking her to marry him, and we schemed to have it framed and hanging up in the restaurant they were going to for dinner. I was so tickled to be involved in such a significant part of someone’s life and story that I ended up refusing payment because it filled me with so much joy to do it. He wrote me back recently:

Six years ago, you created the most beautiful artwork to help me propose to my wife. Six years on, Tomorrow I’ll Be Brave is the first book I’ve preordered for our first child (to be born early July). I hope the years in between have been good for you, Jessica. As creatives, we have followed your career with interest. We’ve finally, hopefully (with fingers still crossed) succeeded after three rounds of IVF. But we have your artwork hanging on our bedroom wall every day to remind us of that most special moment.

It’s pretty impossible for me to not get teary-eyed over that. I’ve never met them in person, but just to know that our stories are woven together through these significant moments is so touching, motivating, heartwarming – all the feelings.

Okay, you seem to be pretty effective at changing other lives for the better. But how do you satisfy your own evolving sense of fulfillment?

Happiness, for me, is about living a life close to people I love with as little stress and anxiety as possible. The first part of happiness is just fulfilling your own and your family’s basic needs. Everyone knows the phrase “Money can’t buy happiness,” but I think that making enough money so that you’re not living paycheck to paycheck, and can make basic purchases for your life and family without stress, is  important in contributing to the ability to be happy. That’s one of the main reasons why I always encourage people to be aware of their basic life and financial needs and factoring those in when “doing what you love.”

I’ve found that I’ve had to navigate away from projects with unpredictable schedules and clients who require late-night and weekend work because of their own mismanagement of timelines.

Some people have the privilege of dropping everything to pursue their dreams but most people don’t. Most people have some form of debt: school, mortgage, or both; someone that relies on them for help: a family member, children; and personal needs – health and wellness – that can’t be ignored. Finding fulfillment is possible once all of your basic needs are met, and once you feel like you have a good handle on managing the stresses in your life.

I find it almost impossible to find fulfillment in my work when I’m derailed by something in my life, like the postpartum depression I experienced with each of my children. It’s all about keeping in touch with yourself, what you need in that moment, and adjusting expectations based on the hand of cards you’re currently holding. It is ever evolving, but that’s okay.

Would you mind sharing more about your postpartum depression?

The postpartum hormonal shift after both of my kids had an enormous impact on me. It was long-lasting, and manifested differently at different times. Sometimes it was crippling anxiety and all-day-and-night looping thoughts. Other times it was really classic depression symptoms, like being tired all the time or not being able to derive joy from things that previously made me happy. It made even minor tasks feel gargantuan, and then it would feel like all these little things I couldn’t motivate myself to do were snowballing on top of one another and turning into a big, out-of-control mess.

For both kids, it took about 13 months after having them to start to feel normal again. It gave me incredible empathy toward people who struggle with mental health issues all the time, and made me see just how toxic our work culture can be when you’re not at the peak of health and well-being. We’re thinking about having a third child, and I already told my therapist that I’m 100 percent going on SSRIs [antidepressants] next time because I just didn’t realize how bad it was until I was out of the woods.

How has becoming a parent changed the way you work in general?

Mostly in what kind of projects I commit to. I’ve found that I’ve had to navigate away from projects with unpredictable schedules and clients who require late-night and weekend work because of their own mismanagement of timelines. I feel excluded from working on last-minute campaigns, which can be very lucrative, because I’m unbending in my boundaries about family time. I have to be more proactive about projects and pursue different kinds of work that can fill the gap left from high-pressure, crazy-timeline agency work.

I couldn’t imagine doing it any other way, though. I know that years from now I won’t have regrets over passing on a client project that could have been cool but would have insane regrets about missing out on key time with my kids when they were little.

Hische photographed in the Bay Area.

Speaking of adjusting the way that you work: You’ve talked about how craft doesn’t scale. Growing your business often means spending less hands-on time with the creative work and more time on less interesting, though necessary administrative aspects. How did you decide to scale down your business?

Part of coming to that realization was just a fear of stepping into uncharted territory. I am a pretty risk-averse person, and making the jump to growing a studio versus managing my own career feels significant. It also puts me directly in charge of someone else’s – an employee’s – future. I love mentoring people and advising others, but having that direct and dependent relationship with someone is definitely intimidating.

Art is my meditation.

Ultimately, though, what I found was that I need to be creating: that the act of making work and spending an inordinate amount of time slowly crafting something is very therapeutic for me. And it helps me manage a lot of the stress and anxiety that I can tend to feel. Art is my meditation.

When you imagine your professional future, what do you see?

I think the not-so-far-away future will mean more writing, kids’ books and otherwise; more making physical products, motivated by having my own retail store; pushing myself to experiment more in different mediums: jewelry, apparel – who knows? Mostly, I want to see where the wind takes me. It feels like it’s been picking up speed lately, and, if I can just convince myself to put my sails up, even if it takes me to uncharted territory, everything will work out.

Sandra Nygaard

Sandra Nygaard is an editorial and marketing consultant. Her work has been featured in Men’s Health, Women’s Wear Daily, New York magazine, and Fast Company.


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