21 Years Without a Boss

My career is old enough to drink, vote, and kvetch about lower-back pain.

On this day 21 years ago, I resigned from my full-time design job at a printing company to become a cartoonist. I was 19. 😳

I didn’t have a degree or a plan—just a second-hand drawing board my mum’s boyfriend found on the sidewalk, a scanner the size of a microwave, and the kind of reckless confidence only a -teenage cartoonist can muster. My first client paid me in “exposure,” which I later learned is Australian for starvation. I’ve been freelancing ever since: cartooning, illustrating, designing, writing, performing—basically doing everything except collecting a W-2 for 21 years.

At my FIT guest lecture earlier this year, I told the students that freelancing is like trying to build a parachute after you’ve already jumped out of the plane. You’re sewing panels together mid-air, hoping the thing opens before rent is due. After two decades, I like to think learned how to fall with slightly better form. But who knows?

I’ve watched the industry shapeshift—from fax machines to email to “could you make that vertical for TikTok?”—and somehow, I’m still here. Freelancing is less a career choice than a long-term relationship with chaos. You either make peace with instability or you spend your days refreshing QuickBooks like a day trader with carpal tunnel.

The hardest part isn’t the hustle—it’s the identity. After two decades without a boss, I’ve realised I am the boss. Which sounds great until you realise the boss is an under-rested cartoonist who keeps giving himself unpaid vacation days and forgetting to invoice. HR is also me. He’s useless.

Where does it go from here? Honestly, I don’t know. Freelancing teaches you to stop pretending anyone does. My hope is that the next twenty-one years look a little slower, a little more selective, and a lot more creative. I still love what I do—the making of things, the connecting with people through lines and gags. The independence that once felt terrifying now feels like oxygen.

So here’s to another year of uncertainty, caffeine, and mild panic attacks disguised as confidence.

No pension, no benefits, no safety net—just a stack of sketchbooks, a flatulent Frenchie who thinks he’s middle management, and the quiet pride of someone who hasn’t had to ask for annual leave since 2004.

If you’ve enjoyed reading this far, consider becoming a paid subscriber to New York Cartoons—it’s the best way to keep the ink (and the coffee) flowing. Or, if commitment issues run deep, you can always buy me a coffee—which, if we’re being honest, is just printer ink in liquid form.

As always, be sure to leave a comment, say hi, and ask a question. I love hearing from you every week.

‘til next time,

Your pal,