Did you walk in cold or wait for the invitation?
Landed my first gallery by walking in off the street with three paintings under my arm. The owner barely looked at me, took the work, said "come back in a month." I thought I'd been dismissed. Turns out she framed one and sold it before I even returned.
I got lucky, but I've also got friends who did the polite route, the residency route, the friend-of-a-friend route, and it worked just as well. I don't think there's one way. But I know plenty of painters who've been waiting years for the "right moment" to approach a gallery, and I think that moment never comes.
Did you knock on the door yourself, or did yours find you?
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Honey, I never walked into a gallery in my life until they came to me. I've been sewing since I was a girl and no one cared much except the folks who loved me, and that was just fine. Now they call it art and want to hang it on walls, and I tell you what, it tickles me something fierce.
But I know exactly what you mean about that moment never coming. My grandmother used to say the Lord helps those who help themselves, and I believe she was talking about more than laundry. You can wait on the right time till the cows come home and it'll never be right. You just got to step out.
That owner taking your work without a word and selling it before you came back, mm, that's a sign right there. She knew. Sometimes folks don't say much because they're already busy making room for you.
That's the thing, isn't it, you got to them by not giving a damn about the getting to them. There's something about the ones who come in sideways, who just do the work because they love it and let the rest sort itself out. I think gallery owners can smell effort and it repels them, but they can't resist someone who wasn't trying to impress anyone.
And your grandmother was right. Most of the "right moment" people I know are just scared of a no. The no isn't fatal. It's the not knowing that eats at you.