Breaking into the Art World: Seeking Participation, Not Permission

Dear Best Friends,

I can’t say I’ve met a lot of people like Caleb. He gives off such a high-energy vibe and generates new ideas at a breakneck speed, but he actually makes things happen, and does them in a thoughtful and structured way. And that’s the other thing about Caleb - there’s structure to his approach, but there’s a good chance it’s structure that he’s just created himself, not necessarily the rules or system that were there before he got there that everyone else is following.

I feel lucky that I got a chance to talk to Caleb - but that’s one more thing about him. He’s a self-professed extrovert, and isn’t shy about making connections and offering his valuable perspective. This is why it’s surprising that, several years ago, he found himself fairly isolated and missing a community in the art world. And unsurprising that he did something about it.

Talking with Caleb reinforced a few key ideas about making it as an artist (or really, making anything happen):

• No one is going to pick you—so pick yourself. If the traditional system isn’t working for you, build your own way in.

• Follow through and follow up. Opportunities don’t just land in your lap; you have to keep showing up, keep knocking, and keep reminding people that you exist.

• Structure creates freedom. Constraints (like themed shows, deadlines, or assigned prompts) don’t limit creativity, they give it a place to grow.

• The art world isn’t one single path. Some artists take the gallery route. Some build their own spaces. Some tell customers at their paint store gig that “sure, I can paint a mural for you!!”

• Community is everything. Even when he felt disconnected, Caleb’s instinct was to reconnect—not just for himself, but for others, too.

To hear about his story and our conversation first hand, check out the YouTube video to watch or listen. You can also find Caleb in the following ways, in case you’re jumping ship now (😢) or would like to reference his amazing work as you read on (😄):

• @colours_pdx for his art gallery

• @rollup_pdx for

• Caleb’s website to see some of his amazing work