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Monday Morning Art School: Should I apply to that show?

Entering shows willy-nilly can be expensive and unproductive. How can you tell what will pay off?
Midnight sail from Camden Harbor, 24X30, oil on canvas; see Hidden Holiday Sale for price.

“When should I enter calls-for-entry?” a reader asks. “There is a plethora suddenly in Colorado. I have pieces headed to a library for their show this winter (no entry fee, but I have to mail or deliver the paintings 200 miles away). Others are going to a museum ($35 entry fee; they keep 25% commission) and possibly a gallery ($35 for three paintings, $50 for 6; they keep 50% commission).

“When is it worth it for the exposure, and some lines on my resume? How can one tell whether artwork actually sells at these shows? When do you stop entering them? Is it all just a vanity thing for amateurs? If one is, like me, wildly experimenting in all directions, does one pick a particular ‘body of work’ to enter, or send a smattering of everything?”
This is a different business model from the one where gallerists assumed all the risk in exchange for 50% of the sales. The art market is changing rapidly, and I no longer think all pay-to-play galleries are inherently bad; in fact, I’m gingerly putting a foot forward in one for next summer.
Farm song, 14X18, oil on linen; see Hidden Holiday Sale for price.
There’s nothing inherently wrong with the models you describe, although I do think 50% on top of $50 is a bit steep. They’re not necessarily just for amateurs, although some are banking on people desperate to get their foot in the door. Many reputable shows charge an entry fee. 
As an artist, you must figure out what return you’ll get for your investment. That’s easiest with local opportunities—just go and investigate the gallery space on your own. Is it a good-looking storefront in a good area, staffed by knowledgeable, competent gallerists?
Not all of us live near a thriving art market. Farther away, the research gets more difficult. If you have a buddy in that area, ask him or her for an opinion. Read the organization’s website carefully, and check the show terms with an eagle eye. If you can’t get there in person, use Google Maps to inspect the street where the gallery’s located. Is it a place you’d go to buy art?
Early spring at North End Shipyard, 14X18, oil on archival cotton panel; see Hidden Holiday Sale for price.
Many of these shows are offered under the imprimatur of established organizations. How long have they been doing the event? Do they have a proven track-record of shows? Google the show itself, something along the lines of “Charming Gallery Annual Landscape Show Artists” and see if you know anyone who’s participated. Contact them and ask about results.
However, you can stand this whole process on its head. This is how I did it: I looked at the resumes of artists I admired and had work sympathetic to mine. (It’s easier today, since everyone has websites.) I noted what shows they’d done and who represented them. Then I researched those shows and galleries.
Early spring run-off, 8X10, oil on archival cotton panel; see Hidden Holiday Sale for price.
That didn’t mean that I expected to get into their current galleries. I’d scroll to the bottom and see where they entered the art market. This required a lot of research across many artists, because galleries and shows come and go. But it taught me a lot.
As for what to send if you’re still ‘wildly experimenting,’ just send in the work you like the best. Acceptance and rejection is in itself feedback.
My Hidden Holiday Sale for readers of this blog is on its fourth day—check here to see all the additions over the weekend! On Friday, the sale goes public with advertising, so your chance for first dibs is limited.