By now Australian calligrapher Gemma O’Brien is used to being watched. The creation of her large-scale, hand-drawn murals has evolved into live theater where she not only focuses on the end result, but also performs for an audience of strangers who pause to view her work-in-progress. Sometimes that means the crowds are literally standing two feet behind her, as she carves out the word adaptation in bold blue, red, and white colors inside a hotel ballroom at the 2016 AIGA Conference. Other times, that can mean they’re gawking from the street, like when she was hoisted into the air by a crane to paint the last of 37 Kirin cider billboards displayed across her native Australia in 2013. Even when raised up in the air, O’Brien still wasn’t alone – by rule, a crane operator joined her in the cabin for safety reasons.

This kind of art creation, one that is documented to show that, yes, indeed, a real person was responsible for what you see in front of you, is the driving force behind’s O’Brien’s belief that the future of typography is human. For as much as people relish the way technology can allow us to escape, there is no escaping the need for a human connection, and why artists who show their processes develop a following that is interested in their work – and them.

O’Brien likens live art to sport. “You can’t just look away,” she says. While an artist, like an athlete, can practice a concept to try and perfect it, the actual performance forces an artist to take a leap into an environment where mistakes can’t be airbrushed out. That, O’Brien argues, leads to the most authentic self of a design, one that can’t be second-guessed or reviewed later with the benefit of hindsight. Rather, it’s purely created in the moment.

Still, even the most spontaneous act can actually be well-rehearsed with a known outcome. Because when the camera and crowds are watching, there is little to no room for error. And when O’Brien is fulfilling substantial commissions for the likes of Adidas, Qantas, and Volcom, she knows the result has to look brand perfect.

We recently sat down with O’Brien, who has been working as an independent commercial artist based in Sydney since 2012, to discuss why authenticity trumps perfection, how she balances artistic freedom with the requirements of brand work, and why she prefers to work at night.

What’s a hand letterer’s role, your role, in the world today?

Within the field of typography, you have such a diverse range of professions and people doing different things. There’s a lot of type designers who are designing the fonts that we need to read efficiently. My work is more in this category of looking at words and thinking of them as art or bringing them into a picture as themselves. That can be to create a beautiful image or add new meaning to words – connecting people in a way that they might connect with illustration or art, as opposed to just the printed word.

How did you notice this pendulum swing from a digital landscape that showed essentially just the finished type or the work to one that brought the human element back to typography?

I started noticing that whenever the illustrations I posted on Instagram had a human element – like me painting or drawing, or even just the textures and tools that I drew with – in them, then it got so much more of a viewer response than if it was only an image. It showed the human scale of someone painting, and people were aligning with that. I think it’s partly that it’s enjoyable to watch humans working.

You’ve compared the live element of making art to sport. As people watch you, there’s a sheer wonder if you’re going to be able to complete your mural without making a mistake, like how someone watches tennis players rally and wonders who will hit the ball out first.

When did you starting drawing this comparison between art and sport?

When I started thinking about this idea of authenticity and how it has played out in the last few years, and then when authenticity became an overused buzzword. I started reading about the ways it was described, and writers were talking about either music, theater, or sport. Then I thought how it applies to art and design as well. Although design was never really imagined in that capacity, because by the time the design is at the point when the viewer sees it, there have been so many revision stages beforehand. It’s almost like crafting authenticity, because the performance part of it is done in the same way people in theater practice their play before the show or sports people train. As a calligrapher, you practice all the strokes before you actually create something. So the art is perfect, but because the imperfections or the mistakes have been removed from the process along the way. Now, artists are starting to bring design back to something that’s a bit more of a lived-in, real experience.

What does this mean for the world of design? Stop trying to make everything look so perfect?

Yes. A lot of the jobs that I started to get off the back of this trend of creating large-scale murals were this fake version of the real thing. Brands might want to do this fabricated chalkboard for the background of a TV commercial, but then the process that went into making it look like it was spontaneous was a little bit deranged or over-planned. Brands like McDonald’s were suddenly bringing out “authentic” chalkboard burger ads, but they’re making them too derivative and forced.

How do you then balance the freedom you want to create something organically with meeting the requirements of the job the brand commissioned you for?

The instances where I find myself the happiest or most creatively satisfied with the work is when I’ve taken a period of time to experiment with either different tools or a new illustration style or scale, and with no constraints in terms of a budget or a timeline. And then that becomes the example for the client to look at and say, “Ah, this is what we want.” At least by the time that it’s then taken into a commercial context, the idea actually had the time that it needed to come to fruition creatively.

Being videotaped while painting or drawing is practically a requirement for your brand work these days. How do you feel about being videotaped while you create?

It really depends. There’s nothing that I like more than being locked in a gallery by myself overnight to paint because I feel the most relaxed. Nobody is watching me and nobody is filming, and I can make creative decisions in the same way that I would on a sketchbook, but on the walls. Whereas, when it’s a live painting for a brand or even at a conference, I specifically plan out something I can make that I know is achievable.

So you win no matter what.

Yes. It is, in a way, orchestrated spontaneity. I know that it is a lot more difficult to be completely free and creative when there’s a camera this close. At the same time, it forces me to really focus on the artwork, because I have to block everything else out in a Zen state. I can feel when people are there watching, but I’ve gotten better at it from having to do it all the time.

What is your daily work schedule like when you’re at home in your attic office in Sydney?

I’m not a 9-to-5 person. I never liked 9-to-5, but I do have a rhythm that is pretty similar each day. If it’s sunny outside I’ll start my day by going for a bike ride or a swim to make the most of the day and then I’ll work overnight. Maybe from 4 p.m. to 2 a.m. or 3 a.m. A big block of time overnight will be where a majority of my work is made.

Why overnight?

Initially, it started because it was distraction-free. There were no emails or phone calls – though now I have an American agent, so there is no free time. I just feel like there is something about nighttime where I get in a less alert state, and that allows me to relax and do the work. It’s deadly quiet, and from the attic I can see the moon. Sometimes, if I have a really hard deadline, I can also see the sun come up. Whereas during the day, I’m very switched on. I’m good at doing phone calls or answering emails or maybe planning a budget or a timeline, that sort of thing. But I’m not so good creatively.

How does that work schedule sync with a social life?

I used to be a lot worse than I am now. I definitely used to be like, “No, I have to work, and it’s so important.” Now, I feel like I can definitely have the best of both worlds. Depending on what projects I’m working on, I’ll usually make time for friends and take breaks.

A big block of time overnight will be where a majority of my work is made.

What led you to stop pursuing a law degree and change careers to become a hand letterer?

I think the reason I studied law in the first place was probably a subliminal pressure from my secondary school to choose a “smart” career option because I got good grades. When I finally was in the midst of the law degree I realized that deep down I needed to be following a more creative path and could never really see myself as a lawyer. Once I had this realization, I knew I needed to make the switch from law to art or design. When I chose design, the field of graphic design was the closest thing to art that had a feasible career. So many designers say that. They either want to design a record cover for their favorite band or they want to be an artist – graphic design is the second-best option and I was probably in that category.

I didn’t discover typography until the first year of law school, and, even then I remember thinking that the idea of working every day only with lettering and typography was not possible. I didn’t know anyone that was doing that at the time and in the industry, there wasn’t anyone who was a letterer. It was pre Jessica Hische. No examples of people doing that. You were a graphic designer or in illustrator. I think the shift in my design degree also happened with the shift in the industry where typography and lettering really grew and the opportunity to just focus on that became a reality. Now, that is pretty much what I do.

What advice would you give an aspiring hand letterer trying to to break into the field?

I think five years ago you could have said, “Get your work out there on a blog or on Instagram.” Now, there are so many people on those channels that I don’t even know if that’s the right way. I have always believed that it has to be about the work first. If you spend the time finding what it is that is unique to you and focus on creating as much of the best work that you possibly can, at least then you have the groundwork to do more, whether it’s meeting the right person or working.

When I chose design, the field of graphic design was the closest thing to art that had a feasible career

What separates good work from not-good work?

In the world of lettering, typography, and calligraphy, it’s difficult now, because a lot of young designers are learning about fonts and typefaces, but they are not learning about the history of calligraphy and writing, which informs “good” and “bad.” There is a fine line between being a really annoying designer who says this is not good because of this and this, and looking at the bigger picture by asking, What do people respond to? For me, that was a big jump to make. Going from, Okay, well it is important to know the history, but how people react on first impression also has value. Maybe it isn’t about being too tedious and specific about the rules but also finding balance between the rules and viewer response.

It’s like how someone who writes a classic book is held in higher regard than someone who writes a mass market paperback best-seller. They’re both good works, but they are judged differently.

Exactly. And you can’t discount something just because it’s popular. The Kardashians, for example. I always think, What is going on? But there must be something that people are connecting with. You can’t just be like, Everyone is stupid.

Your typographic work takes on many forms – calligraphic brushwork, illustrated letterforms, digital type, hand-painted murals, and even fine-point-pen drawings of puke puns on airplane barf bags. Why pursue different styles, even within the lettering family?

I know a lot of designers who think you need to have a style so that people know you for that, but I think that, especially within typography and lettering, the restraints of the alphabet are enough. I always wanted to show a different range of skills and styles within what I do, so that people were not pigeonholing me into one particular style.

Some of your greatest competition for jobs in the future might not be only your fellow artists, but from robots that can mimic hand movements and produce calligraphy. That’s freaky. How do you feel about this?

I find it interesting because I’ve started to think, What are the real applications for this? Other than the company in New York [Bond] where they are using robots to create handwritten notes.

Yeah, robotic, handwritten notes. That is an oxymoron.

Yes, I would never do that for anything other than the novelty factor. I’m curious to see if it does have a big audience and there are people who have robots write sentimental notes. I mean, what other applications would there be in daily use for a calligraphy robot?

Brands could hire a robot to do their hand-drawn work cheaper and faster?

Exactly. But then it takes away the value of it being done by hand. There is a Japanese robot that is interesting because it was taken to a Japanese school and used to teach some young Japanese students Japanese calligraphy, while a teacher was also there. I like the idea of that in the future. Imagine if we end up having some bionic arm on a human and then you could just download Gemma O’Brien’s Brush Lettering program and your bionic hand guides you through the letters. You wouldn’t need to come to my workshop. You just download the software into your bionic arm and then you get the pen and you can do it yourself. Could it go that far?

I have always believed that it has to be about the work first.

You’re traveling around the world for work, while you remain based in Sydney. Have you ever thought about leaving for a new creative environment, like New York City?

In the last few years I’ve thought that maybe I should move to New York since it’s the thing for all of the creatives in Australia to do. But after seeing all these other cities I realized that I really liked Australia as a place to knuckle down and do the work in between all the travel. There is a small but growing creative community there with lots of amazing letterers, artists, and a street art scene. I actually got asked in an interview once, “Gemma, all the best letterers are in Brooklyn. Why don’t you live there?” Because so many styles are shared instantly online, being in Australia is the right place for me to create great work. It’s isolated, I don’t have any distractions, and being there allows me to tap into something creatively that’s completely unique to the rest of the world, my surroundings.