The First Campaign is Always A Bust

Wherein my accountant plays a pivotal role in my quest to become the Michael Keaton Batman

I was about a quarter of the way through the gauntlet-like path to survive 2023. I had already lost a substantial portion of my income as my retainer contracts for design jobs ended. Looking into the vast emptiness of the future would sometimes make me throw up in my mouth a little bit.

Me and my accountant meeting about the future of my career.

I was now also having semi-regular “raised voice” video chats with my accountant who genuinely wanted to help me figure this shit out. He had seen me build my freelance design company from the beginning, and I think he got worried when I started talking about throwing my entire business away and moving to Asia like some kind of sad fugitive who wore linen pants and Crocs all day.

He had assisted me in shoring up some funds to make sure I would be able to financially survive for the next little while. For that, I was thankful. But the panic had bonded us in a slightly uncomfortable way. Like the talking boil that Richard E Grant grows in How to Get Ahead in Advertising:

He was trying to be nice, but also gave me suggestions that made me panic even more. Like starting a YouTube channel where I read children’s books out loud because he low-key thought I had a funny voice. WE’RE JUST BRAINSTORMING HERE, GODDAMMIT.

“Just get yourself and your work out there, Ginger. Nothing is ever going to happen if you don’t let people know about your business!”

The cold fear of the unknown slithered up my butthole and I couldn’t clench my cheeks hard enough. Just like Bruce Wayne, I used that irrational fear to build my portfolio with random pieces of self-initiated work. It was not very good.

In spite of that, I began reaching out to a bunch of folks to let them know about my recent transition into illustration. But just people I actually knew, because I was super terrified of the cold email.

This list included old teachers and professors back in art school, colleagues and coworkers who have long ago achieved dizzying heights of success, and previous clients/friends who were still showing up in my Gmail auto-complete contact feature. “HEY REMEMBER ME? IT IS ME, GINGER, YOUR OLD PAL! I FIXED YOUR PLUGIN THAT ONE TIME IN 2013? I DO DRAWRINGS NOW.”

It was the most awkward coming-out tour. I felt like Miley Cyrus trying to shake off her Hannah Montana persona, wanting to declare it so loud as to make it feel real. I didn’t know how else to do it, but I knew I had to do something. I didn’t have Facebook anymore, and given my current experiences with Instagram, I didn’t feel like taking back yet another ugly stepchild.

Speaking of Ugly Stepchildren…

I had actually forgotten that I had a LinkedIn profile. Someone from the Inkygoodness Collective suggested it as an outreach tool.

There was a specific stretch of time where the platform just would not stop sending notifications.¹ It was like a glitter bomb of emails, and I clearly remember screaming into my laptop for it to stop, even after I knew had unsubscribed to everything.

I don’t know, but I guess someone in their devops or syspos department got fired because all of a sudden the emails did disappear. And because of the silence, it was one platform that had escaped my social media cull. My LinkedIn profile floated along internet rivers smoothly and quietly like a Baldwin brother inside a Hallmark movie.

And just like the Baldwin brother that showed up in Jesse Stone: Night Passage featuring Tom Selleck, it popped back into my life with a side glance and a wink.² I wasn’t entirely sure if I was grossed out or slightly turned on…

I clicked through a bunch of LinkedIn profiles and sent out a lot of emails to say hello. Most of the people I contacted knew me from 15-20 years ago. I understood the discomfort of their expectations not aligning with reality. I felt like I was inadvertently catfishing my colleagues.

It was a mixed bag of reactions, ranging from friendly coffee meetups to funny life updates to short messages. I had some wonderful people put forward some recommendations and endorsements, which truly warmed my heart.

A handful of correspondences didn’t go very well, though. Some people politely declined giving me any recommendations or leads, and some moved away from talking about illustration all together.

I didn’t take any of it personally. It wasn’t all that different from me making eye contact with a Greenpeace activist across the street, smiling, and then pretending to have forgotten something and quickly turning the corner instead.

Also, some people turned out to be real weirdos.

At the end of the day, I had more great conversations than dead ends. No jobs, but it got me out of the house to meet up for coffee or lunch dates with people with whom I had long ago lost touch.

The Sad Truth

In that early stretch of 2023, it took a lot out of me to put myself out there. But shit, I hoped my accountant was happy.

My friends were supportive and encouraging, as it was the polite thing to be when a puppy was sniffing at your leg. However, the painful truth was that I still had a long way to go into developing the illustration skills and portfolio that would get me over the fence.

Even with the handful of pieces I was proud of from the Inkygoodness Make Your Mark program, they still weren’t enough to convince Luniz to put 5 on it.

My expertise and my comfort level were all rooted in graphic design. I knew principles and foundations that were somewhat related to illustration, but nowhere near the same.

Compounded by the fact that I had spent 12 years working in the very niche industry of “visual programming software”—which was basically saying, “I worked in the Ghostbusters Department of Electronic Music Software”—I was really grasping at straws for obtaining any commercial illustration opportunities.

This was where I also realized the merits of self-initiated work: pieces that not only showcased your skills, but expressed your values and beliefs 100%, without a client or a boss dictating the message or asking you to “make it bigger”.

In the years I’ve worked, I never put in the time to develop my personal practice. It showed in my early pieces and people saw right through it. It was Julia Roberts in Runaway Bride eating all those eggs. That realization broke my heart.

I thought it might just be like getting back on the horse. But as Derek Zoolander quite astutely put it, “Sorry, Maury. I’m not a gymnast.”

These conversations made me evaluate my portfolio through different lenses: art director’s, creative director’s, book publisher’s—they all shook out the same answer: My work wasn’t there yet.

The thing was… this was totally okay. A younger version of myself would have taken all of this the wrong way and given up right there; the 8 Mile notion where I only had one shot to make it.

I used to think that failures were the end of your life. Once you missed your window of opportunity or made the wrong choice, it was over. I don’t know about you, but I learned that this was never the case. Elizabeth Taylor had seven husbands. Miley Cyrus won her first Grammy this year. Britney Spears was free! That Baldwin brother was probably going to pop up in another movie one of these days. Opportunity was not a finite resource—as long as you kept up the good fight.

All this being said, the main message I got from reaching out to my immediate circle was: The flowers were blooming, but the fruit wasn’t ripe. I had to take the time to make sure I ripened like the brownest, softest, saggiest, spottiest banana so that I could become the very best banana bread loaf!

Reoriented Expectations

With that very soft launch, I retreated back into my cave with new determination and developed a much more rigorous game plan. Like with every superhero movie, the first act always includes a costume malfunction or some kind of plan going awry.

In a way, this was me and my accountant at the beginning of 2023:

And I had to find ways to get myself to this by the end of it:

Part of this process was an honest look at myself and my skills. And instead of being a baby about it, it was time to see where the standard was and rise up to it. Not everyone can bat a thousand. Or so my sports-obsessed husband likes to tell me. I don’t even know what that means. Is that like a baseball version of a credit score? Anyway, after this experience, I believed it.

1. I found a 2014 Lifehacker article about this! Digitally preserved outrage!

2. YES, I WATCHED ALL OF THE JESSE STONE MOVIES AND I REGRET NOTHING.