illustrated type

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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Wesley Bird

Wesley Bird is an Art Director, Illustrator, and Designer currently living in Los Angeles, California. 

After majoring in painting and printmaking at San Diego State, Wesley got her start working in the art department at Hurley. Three years later she moved to Sydney, Australia to work with Hurley's International division. Wesley currently works as an Art Director at Society6, responsible for all marketing creatives and initiatives. As a freelancer she has illustrated designs for home goods sold exclusively at Urban Outfitters, created custom apparel graphics for Mate the Label and Daydreamer LA, and illustrated type projects for clients and personal promotion.  

Tell me about your path to becoming a freelance designer, illustrator, and art director. 

It evolved pretty naturally actually. I studied painting and printmaking in college and interned at Hurley after my first year of school. It was there that I learned how to use the Adobe design programs and all about apparel design, production and printing techniques. After school I worked for another surf company doing apparel and graphic design. It was a very small company so I wore a lot of hats and just learned along the way. I worked on tech packs, marketing materials, apparel graphics, went to design tradeshows and grew a ton. I then went back to Hurley to work in the art department and design women’s apparel graphics and textile prints.
After a few years, I started to feel a little burnt out on apparel and made the shift to marketing design at Society6. When I started there, our marketing team was myself and one other person. I was given the freedom to build a lifestyle brand with very little direction and hand-holding, which meant I learned how to shoot lifestyle photography, build emails, create marketing campaigns, and learn how to read data so I knew what was working and what wasn’t. It was an incredibly eye-opening experience, and again, I learned a ton. After almost two years at Society6 I was promoted to Art Director and that’s what I am currently doing while freelancing on the side.
I think it was important for me to get a degree in fine art. It helps me as an illustrator to not feel confined by my computer. If there is something I can’t solve with a cursor, I can pick up a pencil and paper and work it out that way. All of my time spent in marketing design helped me learn best practices and become a smarter and more effective creative. I know some people do just fine starting out as freelancers and I am incredibly impressed by these people, but I am definitely not one of them! I needed the structure of a full-time job, a corporate environment, difficult bosses and creative directors to thicken my skin and teach me better communication skills to be an effective freelancer. Everything I learned in my early days of design shaped who I am now and taught me skills I can offer my clients now as a freelancer! It also taught me accountability, organization, and patience. All of which are incredibly important when working for yourself!

"If there is something I can’t solve with a cursor, I can pick up a pencil and paper and work it out that way."

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

Honestly, it was from posting my work on Society6. At the time, back in 2010, they had a licensing program with Urban Outfitters and I was selected for inclusion in their print shop program. My art prints were sold on and in their stores and it got me a lot of good exposure. From there I just started to get freelancing requests from clients who had seen my art at UO and it just kind of went from there. At that time I was also working in the Art Department at Hurley, and as I posted the work I was doing there on my website and social I got a lot of interest that way too.

Do you have any tips for being your most productive? 

I make lists and love checking off items. I am also a huge advocate for taking breaks and going outside. Thankfully, I have a dog on a schedule so it forces me to get out of the house and walk a few times a day without a screen in front of my face. Also, I know I work best in the morning so I try to knock out as much work as possible while the juices are flowing and then I stress less in the afternoon. I have a lot of friends who are most productive in the afternoon so it’s just about knowing when you’re at your best and taking advantage of your energy and inspiration! 

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

I am not the most patient person and I expect a lot, sometimes too much, from myself. These are pretty terrible traits when it comes to freelancing haha. We’ve all had those clients that drive us up the wall, give terrible feedback, and very rarely, make us hate our jobs. It’s in those moments of terrible impatience and intense personal pressure that I have to remind myself how grateful I am to have these talents and be able to create for others.

What is your favorite thing about freelance?

Every new project is so different! I love the variety. I also love the feeling of wrapping a project where the client leaves stoked. That “feel good” moment is probably the best part.

How do you continue to attract your ideal clients? 

I think it’s important to stay active on social media, post on your blog if you have one, and keep your website fresh and up-to-date with your best work. In periods of less freelance work, create work for fun that represents your own design style. The ultimate goal as a freelancer is to attract clients that want you for you, not just someone who knows Photoshop and can follow orders. So constantly post personal and client work that you are proud of on your social channels. Social media can serve you in two ways, it can act as a mini work and life portfolio and it shows potential clients that you are busy and have other work. This makes you relatable and desirable. The ultimate win, win!

"In periods of less freelance work, create work for fun that represents your own design style."

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

This is my ultimate least favorite part of freelance work (doesn’t every designer say this?!). I am pretty bad at responding quickly to emails, but it’s one of the things I promised myself I would work on for 2016. I literally have to schedule an hour a few nights a week in my iCal for answering emails. If I don’t schedule it, it doesn’t happen and emails (aka projects and MONEY) just get lost in the void.
Invoicing is my favorite admin thing to do because I actually fully designed out my invoices so they look rad - and I kid you not, just doing that made the whole process way more fun for me. If that’s what it will take for you to get stoked about invoicing, do it! I tricked my mind into thinking it’s fun haha.
Lastly, definitely hire an accountant. I married one so I totally lucked out (he gets weirdly excited about doing our taxes). But don’t let the stresses of trying to figure out how much you owe the government get in the way of your happiness. You will be more organized and productive and your quality of life will just be better if you hire a professional.

Since you still work for Society6 and freelance on the side, do you have any advice for maintaining a work-­life balance?

Honestly, it’s hard! But having a full-time job has actually given me the freedom to be pickier about the freelance I take on. I am pretty good about knowing my limits so if I know I simply can’t handle one more thing, I will say no. I think it’s okay to do this. Not only would you be sacrificing your quality of life, but you’d be giving your clients less than 100%. I have had clients wait a decent amount of time until my calendar cleared up just to work with me. People respect honesty.
I’m not going to lie though, there are times where my husband has gently told me to shut down work for the night. Know your limits - and if you have a partner, know their limits too :)

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

Great communication skills, Organized, Efficient

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Leah Goren

Leah Goren is an illustrator and surface pattern designer living in Brooklyn, NY. She graduated from Parsons School of Design in 2012 with a BFA in Illustration. She has worked for a wonderful list of clients including Anthropologie,, Chronicle Books, The Land of Nod, Loeffler Randall, Penguin Random House, Vanity Fair, & Vogue.

Tell me about your path to becoming a freelance illustrator.

I studied illustration at Parsons School of Design, and graduated with a BFA in 2012. I opened an Etsy shop while I was in school, and it became successful, enabling me to support myself and get out my work to a huge audience at the same time. This wasn't that long ago but it feels like a different era of the internet. At the time, Etsy was new, and fashion and lifestyle blogs were huge. There was a big demand for handmade or illustrated goods, and in 2010 not everyone had a shop like they do now, so my work stood out more. Over time, I transitioned from having an Etsy to an independent shop platform, and from focusing on my shop to steady client work. I have so much work now that my shop is closed, but I hope to reopen sometime soon!

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

Really just from my shop and the internet. I've never done anything to solicit work other than put my work online—I'm too scared to just email art directors! I've always had a blog, and I switched from Blogspot to Tumblr when it felt necessary. I also started using Instagram in 2011, shortly after it started, and it's been a really great publicity tool.

Do you have any tips for being your most productive?

I keep a very consistent schedule and almost always do the same things at the same times every week. I know that I will be at the studio from 9 or 10 to 6 or 7, my allergy shot is Tuesdays at noon, Pilates is Friday at 10:30, etc. This is probably just my OCD and not an actual tip, but it works. I write everything down in a calendar (well, it's Google calendar now) and make a lot of lists. I also keep pretty good track of what actually is a priority. I just don't procrastinate on things when I know they have to be done. What I do put off is emails that don't really need to be sent, or tasks like filling out this interview!

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

There hasn't been one defining struggle, but in general I don't always know how to do everything I need to do, and it's up to me to figure it out. Knowing what to charge and handling contracts are a couple issues that have gotten much easier over the years. My creative process has gotten a lot easier too, and I have a better idea of how long projects will take and what I'm capable of. But I still have problems with tons of stuff! Health insurance confuses me so much, and I still barely know how to use Adobe Illustrator. And just today I was setting up a new computer and having mini-meltdowns about almost deleting important files from Dropbox and the Wacom pen sensitivity not working in Photoshop. So, it's always something, but I'll always be learning.

What is your favorite thing about freelancing?

Even though my schedule doesn't vary too often, I love having control over it. I can travel any time I want to, I can be sick any time I want to, and I can go to the beach every day in the summer (if I don't have any work!).

"I can travel any time I want to, I can be sick any time I want to, and I can go to the beach every day in the summer (if I don't have any work!)."

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

I use a program called Billings for invoicing. I don't know if it's the best (it probably isn't) but it works for me. I also hire someone to do my taxes. That's about it though. I know some illustrators have agents so they don't have to deal with the business side of their work, but I find that it really doesn't take much of my time.

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

Having a studio separate from my apartment really helps. When I used to work at home there was very little divide between life and work—it's hard enough as it is because my job is so tied to my identity. Also not working too much is important. I almost never work on weekends and try to go home at a reasonable hour every night. I always like the idea of working endlessly, but in reality I need time to reset at the end of the day.

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

independence, work ethic, talent or skill
Photo by Arden Wray

Photo by Arden Wray

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