Illustration by Oscar Bolton Green

In anticipation of the 2016 AIGA Design Conference less than one month away (October 17-19 in Las Vegas; register by October 6), we’re getting an early dose of the kind of the design inspiration attendees can expect by hosting six conversations with 12 AIGA Design Conference speakers we just couldn’t wait any longer to meet.

Hailing from different sides of the world but sharing a love of lettering, Jessica Hische and Gemma O’Brien are two of the designers that have led the hand-lettering explosion of recent years. While artisan chalkboard letters are two a penny today, this pair’s innovative and highly skilled approach to typography, illustration and design elevates their work way and above Pinterest board fodder.

Jessica Hische, 15 Things We Know for Sure

Hische grew up in Pennsylvania, majored in graphic design and took on a grad job at Philadelphia’s Headcase Design in 2006. Before long she was headed to Brooklyn to work with design studio Louise Fili, before plunging headfirst into freelance work around seven years ago. In that time she’s worked with clients including Wes Anderson, Penguin Books, MailChimp, the New York Times and Wired.

Gemma O’Brien, Outsidelands

O’Brien studied design in Sydney, and on graduating worked as an art director at Animal Logic, Fuel VFX and Toby and Pete before going into freelance illustration in 2012. It proved a great move for the Australian, who now counts the likes of Adobe, Playboy Magazine, Nike, Adidas, and the New York Times among her client list. Her work can now also be seen as large-scale murals and in gallery exhibitions. Here, they chat about life, work, and karaoke.

Gemma O’Brien: What are the pros and cons of being at the top of your game? 

Jessica Hische: There are definitely a number of pros, especially if you actually feel at the top of your game (which I do occasionally but not all the time). Having the power to negotiate pricing and contract terms confidently with clients is a big plus. Everyone at every level has the option to negotiate for better contracts or higher prices, but it’s not until you get to a higher level professionally that you know when you throw out a high number or a contract hard-line statement that, if a client wants to work with you enough, they’ll concede. Another big pro is feeling a real sense of belonging within the creative community, both locally and globally. It can be so hard when you’re just starting out to have the confidence to show up at an industry party alone to try to make friends or network. If you can make it in any given industry for 5, 10, 15+ years, the world becomes smaller and smaller. Suddenly you have friends and colleagues all over the world. I think that happens whether or not you get “famous”—if you’re tenacious and social it just happens with time. 

The big con for me is always feeling like I have to live up to other people’s expectations (which are, generally, expectations I’ve put on myself). I find that I worry a lot about whether projects are “a step forward or a step back” professionally—something I was unconcerned about when I was younger. When you’re first starting out, there’s no where to go but up, and it feels like there are a thousand different directions that your career can take (which can be really scary, but is also very exciting). Once you’ve continued along a certain path for a long while it can be really difficult to change things up. 

O’Brien: What drives you to keep pushing your work to a new level? 

Hische: Most of the time, boredom. If I can’t get excited about a project or dread working on it, I know that I haven’t pushed myself to try something new or challenged myself enough. That’s not to say that every single project I take on is about pushing myself to new levels (I don’t think my brain/body could handle that at this exact stage of my life), but I try not to repeat myself. Seeing other people’s amazing work can be motivating, but I find it more intimidating than anything. 

Gemma, how do you balance a lot of personal, or non-commissioned projects, with client work?

O’Brien: I studied graphic design so that was focused on traditional brief-based projects, but I had a drive to do personal projects. One of the first iterations was a large-scale gallery project with my ideas behind it, and that was the first time I did a mural. That really shaped the direction of where my career went, because it was what people had seen.

So do you find you’re commissioned for similar projects you’ve done before? Can you almost manipulate the sort of work you’d like to be commissioned for, by making it as personal work first?

O’Brien: There’s almost a cycle where it starts with experimentation, and it’s a new style, approach, or content. Then shortly after there’s commercial requests for something similar, so that hardest thing is to make that time to try our new ideas so that you’re constantly developing. That’s what I had in mind with the exhibitions, to show something people maybe didn’t know I could do.

O’Brien: How many jobs do you say “No” to each week? What’s your criteria for saying “Yes” to a job? 

Hische: If I answered my emails more frequently, I would have a better assessment of this (I answer incoming client emails immediately but can take some time to answer emails about speaking/collaborations etc.). My rep fields all of my incoming requests, so if something is definitely not right for me or doesn’t fit my schedule at all, he sometimes doesn’t bring it to my attention. Anywhere from “a few” to “a dozen or so” would probably be the right answer. Generally the things that make me say yes to a job are:

  1. It has to be somewhat interesting (doesn’t need to be the coolest project ever, but I can’t slump into my chair at the thought of putting it on my calendar).
  2. The budget has to be reasonable (which doesn’t mean it has to be high, it just has to be appropriate for the job).
  3. It fits into my schedule.
  4. The client knows how to manage their and my time so that I’m not working late nights or weekends (which I only do for the most special of projects or the most giant of budgets)

Hische: You seem to travel a ton for speaking gigs and workshops as well as location based client work (murals and such). What does that mean for scheduling other client work? How do you fit it all in without pissing everyone off? 

O’Brien: A lot of the travel seems to be booked in quite far in advance so I just schedule in jobs around that as they come up. It definitely can become difficult when deadlines blow out or schedules change–I don’t really like to do a lot of computer work while I travel so it does put a bit of pressure to fit projects in around this. But I like the balance of studio work and murals an speaking gigs so I try to make it work. 

Hische: We’re both public figures in the lettering community as well as ladies—have you ever had a fan (male or female) step over the line of what’s acceptable? Have you ever dealt with trolling online?

O’Brien: I think I’ve been pretty lucky–nothing stepping too far over the line other than a couple of rude comments on Instagram which I usually just ignore. 

Hische: Have you found that as others tighten up their online social profiles (creating very curated snapshots of work life) that you’ve had to do the same? If you have, how do you feel about it?

O’Brien: I never originally used social media (mainly Instagram) as a means of self-promotion for my work. However over time it just gradually shifted more in a professional direction. I found it was a good way to share the process of my work as well as travels and inspiration, not just the final product. I definitely feel its a little more curated now and silly pictures or anything too personal is left out. 

O’Brien: How do you think new technology will shape the future of lettering and custom typography? 

Hische: Of course, we’re all influenced by the tools we use. The main thing is that when a tool becomes trendy (any tool, analog or digital), everyone who uses it makes similar looking work. Diversifying your tools is one of the best ways to make work that is different from everyone else. If you can create your own tools (analog or digital) or at least not rely to heavily on fancy shortcut automation and have the history / letterform construction knowledge to make solid work, you’ll be in the best place.

Hische: What’s your least favorite interview question?

O’Brien: Ahahaha… “What’s your favourite font?” and “Have you ever made a spelling error in one of your murals?”

Hische: Who is the most interesting person you met in the last year?

O’Brien: I had an Uber driver who took me to the airport on my recent trip to America–we got chatting and I learnt that he makes surf films and recently directed one for Paul McCartney. He was pretty interesting!

What do you listen to while you work? 

Hische: Erik (Marinovich, my studio mate) is mostly in charge of our office’s Sonos, and we tend to listen to a lot of hip hop. When I really need to get stuff done, I need silence for sketches/ideation, and then something spoken word for the production parts (like podcasts, or “watching” TV/movies with a lot of dialogue). My favorite podcasts are Radiolab, This American Life, Stuff You Should Know, Freakanomics, Criminal, and The Brian Lehrer Show, which is a NYC news podcast I’ve been listening to since I lived there).

O’Brien: What’s your go-to karaoke song?

Hische: So many, but definitely:

  • Oasis, Don’t Look Back in Anger to end the night
  • The Cranberries, Zombie 
  • Boyz II Men, End of the Road, as a duet with my husband
  • Celine Dion, It’s All Coming Back to Me, if the crowd is right
  • TLC, Creep (or really anything by them)

Man, like a million more. Can you tell I love karaoke?

See Jessica Hische at the Craft Symposium and Gemma O’Brien on the mainstage.
Illustration by Oscar Bolton Green