Jessica Hische is a lettering artist, illustrator, author, and self-described “avid internetter” who needs no introduction. She has become as well known for her side projects as she has for her client work and some of her clients include Wes Anderson, The United States Postal Service, Tiffany & Co.,and Starbucks. She shares openly what it's been like going back to work after having her first baby, managing personal and client expectations, and what she loves most about her work. It was an absolute pleasure talking with Jessica and her interview is filled with insight and inspiration. Enjoy!

I know you have a million different projects on the go at any given time. What's keeping you busy at the moment, what are you working on right now?

It’s a little complicated at the moment. I was working on a campaign for the Oscars which ended up getting killed. They were looking for a really loose style and the work I was turning over was just too tight for them. The creative director and I got along like gangbusters though, so it was a lot of fun to work on, but ended up killing my calendar for a month.

Right now, I’m working on an ad campaign for a hospital. It involves me doing watercolor paintings-that’s really out of my comfort zone which I’m psyched about! I’ve been feeling inspired to take on more challenging work. Pushing myself to do more interesting, and weird stuff since I’ve been back to work. I’m a parent now, but I’m not a brand new parent anymore, so getting back into the workflow and trying new types of work has been fun.

I'm also working on a couple of logo projects that are finishing up. I try to only take one logo project on at a time. I want to devote as much as I can to the client when it comes to a logo and their branding because it’s an emotional process for everyone. I just did a poster and catalog cover for a show here in San Francisco at the Letterform Archive. I've been trying to do flocking on them and finding printers that do flocking still was harder than I thought it was going to be. It's like a psychedelic poster that's going to have pink flocking on it, that fuzzy texture.

On top of that we just bought a house, so I moved last month!

Do you plan how many projects you take on around different things that you know are going to be going on? For example, speaking engagements, moving etc.

For sure. When I have a lot of stuff going on, it's difficult to keep my schedule as busy as I would like it to be. I'm one of those people who is most productive when I have a little too much to do. If there's any holes in my schedule, I will fill them with leisure [laughs]. I will find a way to have a two-hour lunch with a friend.

Speaking and travel is the hardest because I have to warn my current clients that I'll be unavailable for a certain amount of time. I've tried working while traveling and it's just miserable. You just can't really be in some hotel on the other side of the world doing work when there are tertiary events to go to. A lot of the reason conference organizers invite you is so you'll actually interact with all the people that are there. It's one of the reasons why I love speaking at events as well.

It's fun to go on stage and talk about yourself, but it's more fun to meet new people and students all over the world. It's really enjoyable and inspiring for me. So if I go somewhere and all I do is go on stage, come off stage and then sit in my hotel room to finish up a project, it's not really worth it.

When I'm planning around speaking engagements, I end up having to do quite a bit of buffering. I’ll tell a client that I won't be available that week, so we need to finish the project up the week before. It's just about managing expectations with clients and being really honest if I’m not available. There are a lot of people that try to ignore whatever they have going on personally, but I think it's important to talk about the realities in your life when it comes to scheduling things. It's a normal part of life.

What would you say are the most challenging aspects of the work you're doing right now?

The most challenging aspect for me right now has to do with my attitude towards the work. I'm having a hard time not getting intimidated by intense schedules or larger workloads since I've come back to work. Before I came back, after the baby, I had much higher expectations of what I'd be able to accomplish in a week. Managing baby duties on top of client work has made my days, and my hours much shorter than I thought.

My work day is from 10:30 AM until 4:00 PM, which feels like no time whatsoever. I can work at night but it's difficult to find the motivation and then I’m exhausted the next day. I have to be in bed by 10:00 PM incase I’m surprised with a 5:00 AM wakeup.

The baby goes to sleep at around 7:30/8, which leaves two hours at the end of the day to reclaim for work but it's difficult to do that. My biggest challenge has just been pushing myself to ramp back up to the level that I know I will be best at. Rather than being overly cautious and just taking on a few projects here and there, if I push myself to take on more work, I will do more work and I'll probably be happier. I'll be more effective at my desk and not fiddling around with email for half the day.

Time management is a lifetime issue and once you feel like you've got it handled, something happens in your life that completely changes how everything is framed. I'm still in the stage of working out my current system. I want to feel like I'm really maxing out my career stuff, but also really maxing out family stuff too. I think I'd be able to forgive myself for a few years of not being the most productive designer, but I couldn’t forgive myself for a few years of not being the best parent.

When you're faced with an unfamiliar challenge, what's your process like for approaching an unfamiliar territory?

I think with everything, I need to break things into easily accomplishable stages rather than think of it as, "I need to make a painting." I ask myself what is familiar about the process to me already. One, I have to do a sketch to start. I know what I'm doing when it comes to sketches because I sketch for every project. Even if I'm doing something in a medium or style I don't work in, I know that pencil has to hit paper first.

I try to turn down the intimidation factor on whatever it is to just get started. Then when I do start, it's not a problem to push myself and experiment more. It's just getting it started that is hard.

No one wants to spend a million hours creating something that is going to look bad—which is why it can be difficult to start projects, especially larger projects. You have to figure out ways to be chipping away at something without feeling like the work you’re doing has to be amazing. Whatever you're doing is helping you get to that final product, whether the work you're doing right now actually contributes directly to it.

If you're writing, you might write a first draft and not use it at all. Maybe that first draft was just to get all the bad ideas out. If you're doing design work, you just have to start thinking and creating something, even if whatever it is you're doing right now will get canceled tomorrow.

When do you know when it's time for a new challenge? To try something that you haven't done before or take on something you're less unfamiliar with?

Since I'm reliant on clients coming to me for what I'm doing in any given week, it's very a kismet kind of thing. I'm sure I could reach out to people if I wanted specific kinds of work but I really like the variability of just letting things happen as they happen. When I start noticing that all the projects coming in are the same kind of projects that's when I stop having enthusiasm to work on those things.

If I'm already getting the feeling by reading the email that it's a project I'm not excited about, I know that it's time to take on different kinds of work. It's just a feeling. Whenever something that used to bring you joy no longer brings you joy, it's time to try something new. It's not that that thing will never give you joy again, it's just that you need some time away. Your relationship with your work is like your relationship with any really close friend. No matter how tight you are with someone, you don't want to have a slumber party for three months with them.

I think self-awareness is the key to success in life. No matter how talented you are, if you don't take the time to think, "is this actually what I want to be doing? Am I happy? Is this work going to help me develop as an artist or bring me the kind of clients that I'm interested in?" You have to be asking yourself those questions. For example, there are lots of designers that will never work for tobacco companies. I'm one of them, because (aside for just not wanting to work for ill-intentioned corporations) if I work for a tobacco company, I can't ever do children's work. You can't be making pretty things to sell cigarettes and then do a children's book. You can't do it. It's a big conflict of interest.

Is there anything you do specifically that helps you manage time amongst your email and communication stuff, versus the design work that you need to do?

I was doing admin Mondays, which are still pretty true, so I never have client deadlines on Mondays if I can help it. For one, Monday deadlines mean I have to work on the weekend which I definitely prefer not to do, so I try not to have a final deadline on a Monday. Mondays are full of answering emails, phone calls and doing all the things that you have to do as a person and as an artist. It’s when I do the things that are not paid work, but are still work that has to get done.

That also helps me say no to things for the rest of the week. So if people contact me and say, "Hey, I want to interview you" or, "Hey, can you fill out this paperwork?" I can tell them that I’ll send it over or deal with it Monday. It gives me a task list so that all those little things don't kill my week. Otherwise, it can be like death by a thousand scratches. Every time you ramp down from work and ramp back up to work, it takes away time.

For managing clients, I use a series of Google calendars. I'm good at understanding how long it takes me to do something, because I have been doing this long enough. When I see a project brief come in, I can generally know how long it will take me.

It's like a puzzle of filling your time. Not only to plot things in a way that you can actually get them done, but also in a way that you're not going to feel burnt out from doing a lot of the same type of work. If I had a bunch of logo projects at the same time, I wouldn't set it up so that I was working on logo briefs for three projects in the same week. That's a lot of hardcore thinking and writing and heavy client time. So I schedule the deliverables for each in a staggered way. It really helps to break it up.

You mentioned ways that you avoid burnout, but do you ever experience it still and what helps you get out of that and motivates you?

I'm kind of in the middle of a burnout session right now. My burnout has less to do with the client work and more to do with just all the other business and personality management things. Since my time in the studio is so precious right now, I get a little upset with people when they send me really generic questions to answer or that kind of stuff. I know that's a total symptom of burnout and I just need to take a breath and take some time for me. It's a combination of things in terms of how I deal with stuff.

Sometimes, I'm just burnt out because I feel like I haven't had a moment to breathe and have a long walk, or lunch with a friend. Sometimes the reason I'm burnt out is that I was bad at saying no to things. The only thing that you can do is promise yourself that you'll be better in the future. I think that that's the thing you always have to think about when you're in the middle of a bad, "I'm not good at stuff" phase.

It’s important to remember that whatever you’re experiencing right now is because of decisions you made in the past. Not because of the decisions you’re currently making. You can take an active role in making your life better but it's okay if that's not felt immediately. You can't expect that if you're burnt out right now, that next week you're just a totally awesome person again. If you're burnt out right now, it means that this is the fall out of the decisions you made in the last few months. The next few months will be better because you'll make better decisions.

What are the five tools that you’re touching on a daily basis right now?

iPhone - I do a lot of iPhoning especially because we haven't had internet at our house. I've been answering a lot of emails and I do this speech-to-texting all the time. I thought I was so dorky but my husband uses it like crazy. I wish I could do that on my computer for answering emails because I like it so much.

iMac - I have a laptop set up but I just ordered a new iMac because I want to not have to commute with my computer anymore.

Adobe Creative Cloud - Mostly Illustrator and a little Photoshop with a bit of InDesign.

Robofont - I also use Robofont occasionally when I work on type design projects. I'll use it if I'm working on a super basic type-based logo because I think differently when I work on type based projects. I over-analyze, and you need to do that for a logo, so I do like to work in that environment when I'm working on type projects.

Wacom - I have a Wacom which I like. I don't love it for vector work but I love it enough for editing sketches and photos in Photoshop that I keep it, even though it bothers me in Illustrator which is the primary environment that I work in.

What was the most recent moment that you had to go out of your comfort zone or do something unfamiliar or something that scared you?

What’s been scaring me recently is the realization that all the things that people with kids tell you are totally true. Wherein it completely changes your perspective on your work.

I didn't feel like I was having the new parent identity crisis until recently. I escaped it for the first eight months some how—when I came back to work she was three and a half months old and even then I thought, "This is great, I'm just a person with a baby, I'm not a mom." [laughs]

It's only recently that I've been having a harder time being as enthusiastic about work as I was in the past. Maybe that's a symptom of me being a little more careful about the kind of projects I take on, because my schedule isn't the most friendly to certain things. Or maybe it's just a thing that everybody goes through. When you have this joyful little human in your life, they really are the best thing and you want to be with them as much as possible.

Before this, work and life were the exact thing for me for so long and I really loved that. I was sad when I lost that. That happened before the baby though, when I moved to San Francisco. My husband had a full-time job and we weren't both keeping crazy hours anymore. So it wasn't like we were sitting on the couch and having work parties until 1 in the morning. He was no longer at the studio working late while I was at my studio working late so it wasn't the same, "work whenever you feel passionate about something" lifestyle anymore. He wanted to hang out with me when he wasn't at work, so it was important to find the balance between spending time together and working on projects.

That has become even more important now because before, I would still work on the weekends if I was really stoked about a project. Now, it would have to be just next level shit to make me work on a Saturday. I just have to have the holy spirit move me in order to want to have a Saturday at the studio instead of hanging out with the baby. It's been scary. It's scary to have your whole vision of yourself totally up-ended, but I think it's just an adjustment period and everybody goes through it.

I'm super glad you said that because I talk to a lot of people who are younger and at the beginning of their careers, and I've talked to people who have had kids, so those two ends of the spectrum are interesting. You have a very fresh perspective because you're right in the middle.

What I discovered when we moved to San Francisco was that being a New Yorker, everybody just works their butts off all the time and they love it. I loved it. I would have kept that way forever. I probably would have died ten years younger but I loved it and I wouldn't have cared. When I moved out here, I realized that, "Hey, I don't have to do 100 portfolio worthy pieces a year to stay relevant." I can have a little more free time in my schedule and that free time helps me make better work when I do work. I need the down time and I need to be healthy.

It was really freeing to feel that I didn't have to be running at a breakneck speed. What I've told a bunch of people is that it taught me that you can actually drop off the face of the earth for upwards of two years and almost no one will notice [laughs]. That was really freeing and made me feel less intimidated about having a kid. To know that if I take six months off of work, it's really a blink of an eye.

That said, it has taken a while to get back into the groove. Clients have almost been too respectful of my time off, and think I'm still on leave. I've noticed that I can't Instagram with the baby because it makes people think I'm still on leave. I have to be conscious about what I talk about online in terms of my personal life. Whereas before, it was just a brain dump of whatever was happening in my life.

Since the biggest thing in my life is this kid, if I always talk about it, everyone just assumes I'm not working. Which I think is really different for guys than it is with women. No one assumes that a guy nine months into having a kid, is still taking off work but it's not an incorrect assumption to think that a woman could be doing that. It's weird.

Why do you do what you do? What makes it so meaningful to you and what do you love about it?

There's two things. One is that I just love the process. It's super meditative for me. I like having constraints. I love the world of design and commercial art. I'm not one of those people that's going to swear off clients forever, because I like the purpose that a client-driven work style brings. There's enjoyment in having someone at the other side of it be happy.

Then there's also the mentorship aspect and the fact that I can be an inspiration for young designers. I'll get emails from them that say I made something seem less intimidating, or they applied to art school because they were inspired by me. That is super-duper fulfilling. Whenever I have doubts about working in an industry that's making things for sale that are prettier, I just have to read one of those and know I'm having an impact. It may not be in a global way like how people that work at life changing start-ups do. It's more of a small scale impact but it's more meaningful. It's a deeper impact with less people.

Who would you like to see on Ways We Work?

I've been wanting to talk to Michael Bierut and Paula Scher, just about how they keep up the stamina of interviewing for 30 years. I really want to have a personal interview with them about, "Hey, how are you still doing this?" My studio mate Erik Marinovich would be a pretty good one as well!