Oldest Guy at the Conference
The persistence of insecurities.
I first attended a Society of Illustrators opening party in 2004. My illustration of Jack Black (as the front man for his band, Tenacious D) was accepted in the Uncommissioned category for the Society’s annual competition and I was over the moon. I had decided to draw it the night before the deadline to mail submissions, thanks to some sudden and inexplicable rush of optimism (I had only a handful of small drawings published in free alternative newsweeklies to my name at the time.)
What the heck, why not?

I remember everything about that trip to New York: my tiny hotel room, the crowded party at the Society of Illustrators building, the famous artists gathered together in the galleries and by the bar, located in front of a big, fat Norman Rockwell painting on the wall. It was the start of something for me; a big step in the direction I wanted to travel as a commercial artist.
But it was not fun — no! It was mostly awkward, confusing, and anxiety-inducing. I was young, inexperienced, unknown, and friendless. The imposter syndrome was crushing.
Don’t get me wrong. I was thrilled to be there, of course, but my excitement over having a drawing in the show (hanging on the main floor, no less!) could not quiet the voice in my head that insisted this was all a fluke.
And I remember, very clearly, having the feeling that I couldn’t wait to be older and further along in my career, with friends and colleagues, a great list of clients, and a “name” in the game.
“Yeah,” I thought, “when I’m one of the older people in the room, I’ll feel right at home. I’ll have made it. It will be sooooo great.”
So last year (roughly 20 years after that Society of Illustrators show), I attended six conferences in six different cities: VIEW in Torino, OFFF in Barcelona, Pictoplasma in Berlin, Lightbox in Pasadena, International in Glasgow, and Annecy Festival in, well, Annecy.
And by this point, I had a “name” in the game. Great! I had arrived where I had hoped to be and was now surely living that easy, breezy life of an established artist, just as I had imagined, complete with friends and colleagues, great clients, and all the rest. Right?
Nope.
In fact, I discovered that my old insecurities were simply replaced with new ones!
20 years ago, I worried about not knowing anybody.
Now, I worried that I only knew older people! Was I out of touch? Uncool?
20 years ago, I worried about not having a body of work.
Now, I worried that my latest work might not live up to my earlier work! Did anyone care about what I was creating?
20 years ago, I was unknown.
Now, I worried that my moment in the sun had passed and I was racing towards irrelevance!
I find it both frustrating and comforting that insecurity is just part of existing, whether in a professional context, or in general life. I naively assumed I would be so relaxed at industry events as an older guy with a couple of decades of experience. It never occurred to me that those more established artists I stood shoulder-to-shoulder with at the Society of Illustrators back in 2004 likely had internal monologues that were every bit as shaky and timid as my own.
It is nice to know, though, that we’re all in the same boat.
Do you have similar thoughts or experiences to share? Please comment below.
Thanks for continuing to subscribe to this newsletter. I know I have been away for a bit. I have some ideas for what The Accidental Expert could become — a podcast (I’d like to chat with other artists …), maybe some tutorials, more frequent and smaller posts with some behind-the-scenes info about art and brushes. And for paid subscribers, I’m interested in maybe hosting some live Zoom meetups from time to time for open question and answers. Any of this sound good to you?
Resources
• Here is a link to the Etherington Brothers’ amazing blog, which has been serving the illustration community for years with fantastic FREE mini tutorials about drawing anything and everything. Check it out here.
• My first-of-its-kind meditative drawing app, Lines of Zen is now available as a one-time purchase. No more subscription. I decided that subs just aren’t ‘zen.’ So, please go check it out here (free to download and includes six exercises, no charge).
Here is a testimonial:
“I feel calmer after just two minutes. This app is a great way to take your mind off of the world and catch your breath. It’s easy to do and totally effective in slowing down my heartbeat and getting oxygen to my brain.”
I’m still really proud of this app and want more people to enjoy it, which is another reason for lowering the price and ditching the sub. Hope you try it and please let me know what you think!
Thanks for reading. Take care of yourselves and each other, remember to be kind, and I’ll say, Ciao for now. — Kyle




The insecurities are indeed always there! I got really lucky in having a chance to get that insight about being in the same boat very early on.
My very first illustration workshop, we did a little side trip to a local college art museum. I don't remember exactly what they said, but I remember walking behind these two illustrators, giants in my eyes, who have been working successfully for decades, and hearing them talk to one another about their insecurities and doubts about their art. It was absolutely this moment of "Holy shit. They feel the same way I do. That means it's not about the feelings going away, but learning to accept and live with them."
I attended an illustration fair with portfolio workshops a few years ago, and even though I was "only" 30, I was one of the oldest people there, and I felt insecure too. Especially because I never made it as an illustrator full time, just occasional work here and there. But it dawned on me that the reason for this wasn't that everyone else my age was off having fabulous careers and didn't need to attend these events. It was more likely that most people had to give up and pursue more realistic career paths. The young people here represented those recently graduated, hopeful 20-somethings, those starting their career, and those who are deemed trendy for a while. Some of them will go on to have brilliant careers like you, and others will switch paths. Maybe it's embarrassing to still have this dream almost a decade later and not get anywhere, and it's hard not to feel envious sometimes. But no matter what, I'll keep trying! It's important to work on your ego and negative automatic thought patterns. I'm sure you're an inspiring role model for a lot of younger artists at these events, and it's an honoured position to help them. I hope you remember you're very skilled at what you do and take it easy on yourself.