Reflections from the Booth: My Time at the Webster Arts Fair
This was my first time showing at the Webster Arts Fair, and I left with sore feet, an empty wall, and a full heart.
Art fairs are wild in the best way—part gallery, part sidewalk confessional, part endurance sport. But Webster had something special. From the start, the energy felt different: welcoming, curious, and surprisingly personal. People weren’t just browsing—they were seeing.
They asked about tentacles. They asked about colors. They laughed, paused, pointed, and sometimes told me how a piece reminded them of something they'd felt but never put into words.
I had collectors return after circling the fair twice. I had conversations that wandered into stories about parenting, mental health, and growing up strange. I even had a few pieces that sold before I could finish setting them down.
What I Learned (and Relearned)
There were big lessons.
First: no matter how much you prepare, it’s never quite enough. Especially when it rains. I discovered—mid downpour—that my tent was no match for Missouri weather. If I’m going to keep doing art fairs, I’m going to need an upgrade. (Any recs? I’m listening.)
Second: less is more when it’s focused. After the first night, my partner gave me a note that changed the game—focus solely on my digital art, specifically the 10TCL Collection. That clarity of vision made a huge difference. The work landed better. The conversations went deeper. People got it.
Finally: connection matters more than polish. I was surrounded by generous artists and friendly chaos. I swapped tape, rain tips, and life stories with neighbors in nearby booths. And I was lucky to see so many familiar faces—previous collectors, neighbors, coworkers, and of course, my family. Their support was like a tent stake in the wind.
What Hit Me Most
The pieces that resonated weren’t always the boldest or most detailed. It was the ones with just enough ambiguity to leave space for the viewer to step inside. That’s always been my goal—but Webster showed me how deeply that can connect.
Surrender (2024)
Original Digital Illustration– 24″ × 36″
One of a kind
The gesture is simple—but what it stands for isn’t.
Surrender is about learning to trust the parts of yourself you don’t always understand.
SOLD
One of the most meaningful moments from the weekend came from a couple who connected deeply with Surrender—a piece that’s especially personal to me. I wasn’t sure it would resonate. In fact, I hadn’t even signed the archival print. It felt too internal. Too niche. Maybe even too vulnerable.
But just hours after I hung it in the tent, they saw it. Really saw it. We talked for a while, and before they left, they asked if I would sign it. That small request hit me harder than I expected.
It was a reminder that the work you think is too much or too personal might be exactly what someone else needed to see.
That right there? That’s the kind of sale that sticks with you.
Gratitude & Gear Check
To everyone who stopped by, shared a thought, or took a piece home—thank you. Seriously. Your reactions reminded me why I do this.
To the artists who helped with tent hacks, tape, encouragement, and stories—I see you. You made the weekend.
To the kid who asked if my tentacles were real… you get it.
A Note of Thanks
I also want to recognize the Webster Arts organizers and volunteers—the behind-the-scenes force that made this fair feel so artist-friendly. From setup to storms, they were there for our needs with patience, professionalism, and a lot of heart. Their support didn’t go unnoticed. It made a huge difference.
What’s Next
A few of the most popular prints from the fair are now available online, including Birdhouse in Your Soul, Be My Head, and Liked. If you missed the fair (or want another look), you can explore what’s still available:
Until the next tent goes up—
Stay weird. Stay open. Stay honest.
—Rob
