I’m an artist, so I can say this: Us artists, we can be super weird sometimes. And when we’re around gallerists, we get even weirder.

When I was Fine Art Chairperson of ASMP NY, I produced our annual Portfolio Review. My job was to find gallery owners to volunteer their time reviewing photographers’ portfolios. One afternoon I was sitting at a downtown gallery, chatting with the owner for what could not have been more than twenty minutes. In that time, seven different artists barged in trying to show her their work—one even pulled a painting out from under his arm. She replied as kindly as possible: “Sir, this is a photography gallery.” His answer: “Okay, I’ll email you.” Her response: “No. Don’t email me. Please, just… thank you, have a nice day.”

I asked her, “How often does this happen?” She sighed: “Every day, all day. Why do you think we hide in the back?”

Is this really how we occur to galleries? Relentless, slightly desperate, and unaware of what they actually need. It got me thinking: how do we stop being that guy and become the artist a gallery actually wants to work with?

Think Like a Gallerist

As artists we obsess: Is my work good enough? Is this framed right? Will they like me? But when you talk to gallerists, you realize they’re obsessing about something else: money. Can you blame them? Imagine renting a storefront in Chelsea, hiring staff, paying utilities, advertising, painting, installing, and covering personal expenses. You’re staring down $20–30K a month in costs before a single piece of art sells. With a 50% commission model, a gallery has to move $40–60K of art every month just to survive.

So when you ask, “Why is it so hard to get a solo show in New York?” The answer isn’t mysterious—it’s math. If you’re already selling $60K a month, you’re in. If not, you need to prove you can “move units”, and that means building an exhibition and sales history. Which leads us to…

The Artist’s Catch-22

Galleries want artists who are going to sell work. To prove that, you have to have an exhibition and sales history. But to get that you need a gallery. It’s a Catch-22, right? 

Well, not necessarily. Yes, it is a closed loop. And yes, it's not easy to break into it, but there is a way. And this is part of your job as an emerging artist. In addition to making great art, it's to build momentum and connections with the right people —people who want to champion you.

And this is a long game. Let's talk about where to begin. Here’s where I detour into two silly but useful analogies.

Relationships, Not One-Night Stands

Working with a gallery is like a marriage. You’re contractually bound, you see each other constantly, and ideally you grow together for years. So when you’re looking for a gallery, you’re not looking for a one-night stand. You’re looking for love.

And like dating, finding a gallery can be awkward, emotional, and full of false starts. And if you don’t put yourself out there, you’ll never meet anyone.

So how do you meet someone and fall in love? 

The Meet Cute
A “Meet Cute” is that perfect, quirky first encounter between our two main characters that sets them off on their rom-com adventure. And yes, this does happen in real life. Don’t laugh! I pride myself on meeting both my wife, and my first gallery in two separate and unrelated meet cutes.  

You can’t engineer a meet cute, it would be weird and slightly unethical. But what you can do is make sure you are in the right place, at the right time, with the right people so that it can happen. 

Step 1: Identify Your Entry Point
Start by organizing your understanding of the marketplace. It’s helpful to think of the art world having these four categories:  

• Artist-run galleries: These are often cool, and great if you’re already part of the community. If you are not, don’t spend time trying to break in unless you genuinely want to connect with that specific group of artists, and be a part of their crew. 
• Blue chip galleries: The big names (think Gagosian, Mary Boone) are not entry points for new artists. Don’t waste time here; when you’re ready, they’ll come to you.
• Low-to-mid tier galleries: Your best bet. Especially the scrappy, lower-end ones. 
• Honorable Mention** Non Traditional Spaces:  Also consider coffee shops, bookstores, salons, etc. These venues offer valuable exposure and a chance to build your exhibition history.—better your work be on a wall than under your bed.

Step 2: Research and Organize

1. Start with a list of gallery openings. This will give you specific events to target, and shows you active galleries that are actively showing work right now. Use resources like artcards.cc to find ALL of the weekly gallery openings in your city. 
2. Second: you need to narrow that list down to only the galleries that might want to see YOU. 
   1. Only focus on identifying low to mid-tier galleries. Our instinct is often to try and “shoot for the stars and hit the moon,” however this does not apply when you are trying to infiltrate a closed loop system. The only way to do that is by targeting the “weak points” in that closed system. Which is not to say these galleries are “weak.” These galleries are an extraordinary opportunity for you to show and sell your work. And once you show and sell there, the larger operations can take notice. 
   2. Look for: Recent year of establishment, younger owners, short exhibition history, or any other “questionable” aspects.
3. Third: Find out where your work MIGHT fit in. Pull up your personal website and pull up a gallery's website on the same screen. Look at them and ask “Does my artwork look like it fits in with this artwork?

Step 3: Go in Person
You must go in person. Art (and love) happens in real life! Once you’ve identified promising galleries, attend their openings. This is crucial. This is the opportunity for you to: 

• See the gallery, see the work, and see what kind of “vibe” the place has. Is it what you thought when you saw it online? 
• Remember a gallery relationship is like a marriage, we spend a lot of time thinking about “will they like me?” But what if you don’t like them? You certainly don't want to get married! 
• The best time to find out what a gallery and its community is like, is during their opening. 

TIP: Bring friends, make it a social event, maybe make it a date! Make it fun— this is your life, you are an artist, grab some artists friends and make a night out of it. 

Step 4: When You Find Your People
When you walk into a gallery and you feel at home, you will know it immediately. Subscribe to their newsletter, attend all their events. Galleries are community hubs, and being present is the best way to become part of the inner circle. 

NOTE: all of the hard work is in qualifying the galleries. There are thousands of galleries, almost none of them are right for you. But when you do the work to qualify the galleries before you go based on the tier of gallery they are, and how the work looks, I promise you you will walk in and you will quickly find your people.

Step 5: The Meet Cute
Don’t force introductions or bring your portfolio to openings. Instead, be open, available, and authentic. If you are open and available, your “meet cute” will naturally happen. It might be with a gallery owner or curator, or even one of the artists represented by the gallery. If you stay open and available, good things will come your way. 

Turning Connections Into Long Term Relationships

Once you meet some folks, and you are invited into the gallery community, these are the next steps to find success. 

Step 6: Get Into Group Shows
Once you’re part of a gallery’s community, you’ll hear about these and meet people and get opportunities to be a part of group shows. These are your auditions—your chance to show your work, demonstrate professionalism, and even sell your work. If you do well at a group show, the gallery will want to go further with you. 

Step 7: Sell Your Work
Group shows are tests for both your art and your ability to engage an audience. Bring supportive friends, encourage sales, and make your work accessible. Selling work at a group show is the next major step toward a three-person show or solo exhibitions and deeper gallery relationships. 

Final Thoughts

At the end of the day, breaking into the gallery world takes more than just producing great work. You’ve gotta be out in the world. It takes persistence, strategy, and a little magic. You can’t control when those magic moments will happen, but you can put yourself in the right place, at the right time, with the right people and when you do, just watch how much magic happens!