EXPO Chicago: A Laboratory (With Better Outfits)

Last week, we got deep into the weeds of “What is Good Art?” It was all very high-minded and philosophical—the kind of theory that feels important until you’re actually standing in a room with 3,000 paintings.

But this week, it’s time for the technical rehearsal. EXPO Chicago opens at Navy Pier in a few days. For the uninitiated, an art fair is a strange ecosystem. It’s 170,000 square feet of visual noise, overpriced espresso, and a lot of Americans trying on the European “air kiss” thing for size.

Before you step onto the Pier, you need a mental pre-game. If you walk in without a “Why,” the fair will decide your “Why” for you (and it will usually be “Buy this shiny thing because the gallerist was nice”).

• Define Your “Why”: I don’t mean pick a wall and shop for it. I mean establish a question or two you want to answer, like “Do I love contemporary Korean art as much as the hype suggests?” or “I’ve never been an abstract art person; I wonder if spending time with it in person will change my mind.” Maybe you are scouting for a five-year collection plan. If you’re looking for everything, you’ll see nothing. Pick a lens—be it emerging photography or textiles from the Midwest—and let that be your North Star.
• The “Non-Buyer” Immunity: Decide now that you aren’t under pressure to buy a single thing, but give yourself space to do so if you are so led. I use a weird reverse psychology trick on myself that removes the dopamine hit of buying by removing the anticipation. I grant myself permission to buy whatever I want. I tell myself that if I see it and love it, I can have it. Ironically, this flips the narrative from “wanting and not being able to have” to “the fair is my bed of oysters and I want to choose the one with the biggest pearl.” Try it next time you’re out shopping. I bet you leave with less than you would otherwise.
• The Comparison Engine: In a gallery, an artist’s work is in a vacuum. At a fair, it’s a chorus line. You can see twenty artists all trying to “reinvent the portrait” within a three-aisle radius. Ask yourself: Which one feels like a discovery, and which one is just a revival of someone else’s ideas?
• Beware the “Visual Sugar”: Fairs love a “Glitzy 11 o’clock Number.” Big scales, neon lights—things that look great on Instagram but feel “thin” after three minutes of actual looking. Notice what stops you because it’s loud, and what stops you because it’s dense.

P.S. I’ll be filming a “How to Walk a Fair” Masterclass for my paid subscribers this week at EXPO. It’s a 10-minute deep dive of me actually navigating the floor in real-time. No “best of” fluff—just my actual method with IRL examples of me working through the filter. It’ll drop next Sunday.

This week’s additions to The Collection come from my recent visit to New York. Geometric abstraction, a fresh approach to the garden, and some unique materials are all on view in The Collection now. All three artists are new to me and should be on your radar too!