There was nothing in Jessica’s early life pointing to her future as a professional cartoonist; she drew a lot (of horses).
But most kids drew.
“I don't think there was any big neon pointer saying, You're going to be an artist,” she tells me.
In high school, she drew an illustration for the school newspaper, but she was primarily a reporter and then the news editor, “because that’s the ‘serious’ thing to do.”
She didn’t take art classes.
“I felt this need to prove that I was serious in some way,” Jessica explains. “Whatever was the hardest thing to do, in order to prove my worth, I would do that.” Even though she loved art, she majored in English at the University of Chicago.
Becoming an artist was not a “serious” pursuit, and no way to make a living. Drawing and reading comics were firmly filed in the “hobby” category.
Until she picked up a comic book that changed everything – the moment when you discover the piece of art that turns you from a fan into a creator.
“I was glued and immediately started thinking about doing it myself.”
In the late 80’s Jessica mostly read superhero comics; there weren’t a ton of other options at the time. So when she read her first issue of Love and Rockets, she knew it was different. It was the first comic book Jessica had ever read that featured people grounded in the real world, not a super universe.
[They] were about recognizable people in recognizable situations, and mostly people in their late teens and early 20s like me, doing punk rock things. I was glued and immediately started thinking about doing it myself.
A subtle dream began.
Love and Rockets was published by Fantagraphics, and while Jessica didn’t imagine she could make a living doing comics, she dreamed of creating a comic that would one day be published by Fantagraphics.
To begin, she created full comics in college, just for fun.
She didn’t know anyone who made a living as an artist, so it never crossed her mind to pursue it seriously. She drew because it was fun. Because she wanted more comics like Love and Rockets to exist in the world. And that was enough.
But what she didn't know then was that a serious world of art and comics did exist, and she was about to become a part of it.
“Win a date with Stinky.”
Jessica graduated college in 1991, during a recession. She moved back in with her mom and got a job as a waitress. “There were no jobs. And also,” she explains, “I didn't know what I wanted to be.”
She read comics in all of her free time. Because even when you go from art consumer to artist, you don’t stop consuming – quite the opposite. Creators committed to their craft consume art more than everyone else – they just consume it differently.
“I didn't know what I wanted to be.”
They pay attention.
They learn from everything they consume, studying how the art was made, trying to work out what choices the artist made to get each emotional reaction.
They also notice the fine print.
While reading an issue of Hate by Peter Bagge (also published by Fantagraphics), Jessica noticed small print in the back of the issue advertising a contest the author was running.
Peter would draw the winner as a new character in one of his comics to go on a date with one of his more unsavory characters named Stinky. It was a kind of tongue-and-cheek contest, a way for Peter to engage with his fans and have some fun, Jessica explains.
To win, all you had to do was write a letter about why you should win a date with Stinky.
How cool would it be to literally see yourself in one of your favorite comics? Jessica entered the contest.
And since she lived in Chicago, Peter asked her to meet him at the upcoming Chicago Comic-Con so he could draw her in person.
Most people would have shown up, met Peter, gotten drawn, excitedly shown their friends and family the issue when it came out, and that would have been the end of it. A cool story.
But Jessica isn’t like most people.
“I can't make a living at this.”
Peter told her to meet him at the Fantagraphics booth.
Jessica didn’t want to show up empty handed.
She didn’t want to show up as a fan only.
She wanted to show up as an artist. A creator, just like them.
So right before the 1992 Chicago Comic-Con came to town, Jessica made and self-published her first mini-comic, Artbabe. “It was a photocopied booklet,” she remembers: “hand-bound with ugly pink yarn, and individually stamped with potato prints.”
It was her first official step into the world of professional artists, pink yarn and all.
The second step?
She showed up in public with it.
Jessica handed copies of Artbabe to everyone she met at Chicago Comic-Con, including Gary Groth (the publisher of Fantagraphics), Eric Reynolds (then writer at The Comics Journal), and Dan Clowes, a well-known cartoonist who was later to be published in The New Yorker, Newsweek, and Vogue (and was even nominated for an Oscar).
She made an impression and got invited to the Fantagraphics dinner that evening, where she discovered a community of professional cartoonists – artists who took their work seriously.
At some point after that dinner, Dan Clowes invited Jessica to come to one of the regular jam comics sessions he'd have with Chris Ware, Gary Lieb, Terry LaBan, Archer Prewitt, and other Chicago cartoonists. They all met up at a coffee shop to pass around a story, each drawing a panel, a kind of madlibs.
Jessica hated doing jam comics – “that was too anxiety-producing for me” – but she went anyway, knowing it would be another opportunity to learn from and be in community with the artists she admired. She brought her sketchbook to the coffee shop, and Dan saw more of her work.
“This is pretty good,” he told her. “Are you planning to be a cartoonist?”
“Oh, well, I want to do comics, but I can't be a professional cartoonist,” she replied. “I can't make a living at this.”
“Why not?” Dan said. “I do.”
At least, that's how Jessica remembers it. Dan claims he would never have said such a thing, which, she admits, is probably true. But what's important is what she heard.
A week later, Dan showed up to the restaurant where she worked and gave her three Hunt No. 22 nibs – special pens for drawing comics – and said, simply, “This is what Jamie Hernandez uses.” (Jamie was one of the creators of Love and Rockets).
For the first time, Jessica started to believe that being an artist could be her primary identity – even if it never became the only way she made a living.
But she was about to start to make a living with her art, and in ways she never saw coming.
“Where have you been all my life?”
When Peter Bagge released the issue of Hate with the drawn Jessica going on a date with Stinky, he also included a plug for Artbabe. It was the early 90’s, so he gave his readers an address where they would mail their money to Jessica, and in return she would mail them a copy of Artbabe.
“And that's how I started selling books,” Jessica tells me.
The Comics Journal also wrote a positive review of Artbabe, and comic stores started stocking Artbabe in stores.
For years Jessica continued drawing, self-publishing, and selling new issues of Artbabe.
And every year, she sent each new issue to Gary Groth, the publisher at Fantagraphics.
She “never heard a peep from him.”
So she looked for more self-publishing opportunities and applied for the Xeric Grant that was started by Peter Laird, one of the two creators of Teenage Mutant Ninja Turtles.
She got the grant, and Artbabe was finally printed professionally. And as was her habit, despite the silence, she sent that issue to Gary. This time, she heard a peep: “Where did you come from?” he responded.
“I”ve only sent you everything I’ve done for the last five years,” Jessica thought to herself, laughing now at the recollection.
He just hadn’t noticed.
Sometimes, being ignored doesn’t mean you’re not good enough.
It just means people are busy.
It just means you have to keep showing up.
In 1996, Fantagraphics published Artbabe Volume Two.
I ask Jessica what kept her going, kept her self-publishing, for all those years. She’s glad she didn’t know how long it would take.
If I thought, when I was 22 that it would take until I was 27 to get an offer, it would've been rough.
But she thinks the not knowing kept it fun.
She compares the comics world to the indie music world of that era, when, before bands like Nirvana, she explains, there wasn't a foreseeable way to make money doing that kind of art; people didn’t play that kind of music with hopes to get rich and famous.
It was the same with comics then: “You just do it because you're punk and you just go and do stuff.”
Jessica had dreamed of being published by Fantagraphics, but she was never under the impression she’d make a living that way.
I wasn't thinking about it as a job. It wasn't like, ‘Oh, I'm going to get published by Fantagraphics, and then I'm going to pay my rent with it.’ That wasn't going to happen.
But that was okay with her. Because making comics was always about more than making a living: “Even though Fantagraphics was my goal, the community was the point. Some of my best friends are still people I met in that period.”
A path to becoming a full-time professional cartoonist didn’t really exist at that time, aside from having “some kind of magical big hit.” But Jessica wasn’t counting on that.
Jessica paid the rent by waitressing, bartending, and eventually working in higher education, becoming an administrative assistant for the School of the Art Institute of Chicago.
She kept going, working at the art school by day, drawing comics by night, and pursuing freelance illustration jobs, like the full two-page spread she did for the free Chicago newspaper The New City in 1995, a cartoon drawing of the local bowling alley that was hosting punk rock shows.
She could have never predicted what was going to happen next.
“You just do it because you're punk and you just go and do stuff.”
She recognized his voice immediately.
In 1998, Jessica moved to Mexico with her now-husband Matt (they met through the comics community, exchanging comics for several years before meeting in person).
She found a friend to make her a website to help her get more freelance illustration jobs while living in Mexico, and also set up a service so that anyone who called her U.S. phone number would hear a message with her phone number in Mexico. They’d just have to be willing to call long distance, not an easy feat back then.
No one called.
For six months.
Until someone did.
She recognized his voice immediately. As a Chicago native herself, Jessica was a fan of This American Life and had started listening before it went national, when it was still called Your Radio Playhouse.
But why was Ira Glass calling her?
Because, three years ago, in 1995, he’d clipped out a two-page illustration about a bowling alley that did punk rock shows – he loved the illustration style and filed it away as inspiration.
When he got the idea to create a comic of how they make a radio show for a fundraiser, he remembered how much he’d loved what Jessica did years earlier. He pulled out the illustration from his files, found Jessica’s phone number via the White Pages, heard the message that gave her number in Mexico, and called her long distance.
Together, they created Radio: An Illustrated Guide.
Years later, she would expand on the idea herself and make the storytelling masterpiece, Out on the Wire, published in 2015 by Broadway Books, an imprint of Random House, one of the biggest publishers in the world.
By then, Jessica had been working on her craft for 30 years.
Even though she never imagined it was possible, she was now earning a full-time living making comic books, also made feasible by a dreamy residency she got in France.
She was living The Artist’s Dream.
She loved living in France, and was deeply inspired by having her calendar all to herself for once – she could just create.
But the pace of making a living with books alone started to become unsustainable.
She loved the work, she really did. But, as she explains, “being a full-time author, and especially a cartoonist, is a never-ending grind no matter how much you love the work…I didn't want to be grinding myself into dust to make a living.”
She wanted to find another way.
For Jessica, each book takes at least three years (some can take up to 12); comics take time. And for Jessica to make a living as a cartoonist, she had to race to sign a contract for the next book before the current book was finished.
She loved making books, but there was no breathing room.
Producing without ceasing took away the flexibility and space to consider what she even wanted to make next. It was the content hamster wheel on hyperspeed.
She missed being driven by freedom. Joy. Community.
She also realized the book-only path depended on a mass-audience business model, and she didn’t have (or want to build) a mass audience. It takes a long time, and is its own kind of lifestyle.
That model wasn’t for her.
She wanted to find another way.
But she wondered if another way even existed.
Was there a way to be a professional artist without millions of fans?
“What do you need help with?”
Jessica decided to ask the audience she did have: what else could she do for them? Maybe there was another way she could provide value in addition to making books?
She wanted to see if she could find a way to make a living in the creative space she loved without being chained to the traditional book production and publication schedule.
She had an email list made up of the artists and storytellers who listened to the Out on the Wire podcast she'd created, the companion podcast to her book of the same name. She emailed them:
What do you need help with?
Perhaps they’d want her to create a comics course? Or maybe help them tell better stories, since that was the topic of the podcast?
But that's not what they emailed her about.
Was there a way to be a professional artist without millions of fans?
They wanted help with something else. Something painful.
They were struggling to produce the creative work they cared about, and wanted to know how Jessica was able to create so much work in the last few decades of her career (by then she’d published close to a dozen books, and had two kids).
They replied with things like:
I can't finish things.
I procrastinate all the time.
I’m so stuck.
I have this huge idea and I don't know how to make it real.
Jessica felt a spark as she read response after response. She remembers thinking:
I know how to do that. I can help.
“The job of marketing isn't to push what you do on people who aren't interested.”
That spark turned into a kind of mission-fueled fury: Why aren't creative people taught how to build successful creative lives? She wanted to fix that.
It was time to step away from the never-ending publishing schedule and start a business of her own. There was just one last hurdle:
[Starting a business] was incredibly difficult and challenging – not only at a technical level, but also at a mindset level. Because, as an artist, I came up through punk rock and comics.
Business is the enemy.
To be able to let that go and understand how these tools can be used by actual humans for good and not just for the destruction of everything? That was tough…that was a really big switch for me.
And yet in making that switch, she gained the tools she’d need to help other artists do the same.
She dedicated herself to learning marketing from people like Tara McMullin, and in 2015, as a way to help all those creatives who were reaching out, she launched the pilot of what would become the Creative Focus Workshop – a course and group-coaching program designed to help serious creatives face down procrastination and perfectionism so they can finish the work that really matters.
She continued to use email to build the right audience of creatives, writing personal emails and sharing blog posts – like this popular one. Her personal style and challenging questions struck a chord with people.
People like me.
(After being on Jessica’s email list for years, I bought and went through the Creative Focus Workshop; it helped me make monumental progress on a book I'm working on, even through an unexpected family health emergency.)
Marketing, like art, could be another way to connect with people, build community.
Marketing didn't have to be the enemy of art. And it didn’t – and really shouldn’t – have to be pushy at all.
Whenever Jessica’s students share their doubt and terror of marketing their art, she tells them to think about something in their house that they bought and love, and to consider what it means to them. Then, she asks: “So why can't you be that for somebody else?”
The big shift for me was understanding value – understanding my value. I believe in what I do, and the job of marketing isn't to push what you do on people who aren't interested. It's to invite people who really are interested to know more about you and to get engaged with you.
What would happen if you looked at what you do as “a gift to people as opposed to a burden?”
With that in mind, Jessica doubled down on email, sharing helpful content, knowing that it takes some people years to make a buying decision.
Email is how I make my money. I just did a launch in February. At least half the people who joined my program had been on my list for a year plus. Four of them I noticed had been on my list for three plus years. They've been sitting there thinking about wanting to work with me for that long.
Jessica's commitment to the long-game paid off. She now runs a global community for current students and alumni of the Creative Focus Workshop called The Autonomous Creative Collective. These creatives from all over the world help and support each other to build resilient and sustainable creative lives so they can make the kind of work they care about.
I'm teaching others the same kind of ‘take control of your own life, build and rely on community, do the thing even though it's scary’ thing that I did when I started out, and is at the heart of the DIY, grass roots, no gatekeepers ethos of the mini comics and punk communities I came up in.
I deeply believe in the idea that we are all capable of being captain of our own creative lives.
And whether than means stringing your first book together with pink yarn or being published by one of the top publishers in the world, the result is the same: when you create and share the work that matters most to you, you make it possible for someone, somewhere, to discover it.
It might delight them. Inspire them. Change them. Maybe make them want to become a creator too.
One thing's for sure – it won't exist without a little bit of punk-rock boldness and a belief that your creative life is in your hands.