Blog / 2024 / Mistake #14: Believing in the Big Break

Last spring, I celebrated my twentieth artiversary, and to mark the moment I’ve been blogging about everyday mistakes, things like people pleasing in my art or publishing art that’s not my best.

Today I’m talking about the idea of the big break and how easy it is to get hypnotized by its false promise. I’ve written about it on my blog before, but I want to share a new perspective on the problem.

My first encounter with the big break myth as a professional was a conversation I had at 24 years old, when a friend told me I was working too hard at this whole art thing. Their point: if I was really meant to be an artist, the universe would be letting me know by bequeathing me with big breaks galore.

At the time, I concluded that my friend lacked imagination in allowing themselves to be sucked in by some Hollywood movie version of artistic success. But their words haunted me and sometimes made it hard for me to see all the breaks I was getting.

Because I may have been 24 and I may have only just saved up enough money to move out of my parents’ house, but I’d already been on a local art radio show that had a lot of cachet, which is to say that I’d already had a decent-sized break. And it only happened because I didn’t just make a body of work and put it on display thinking that would get people talking. I worked “too hard” and sent out press releases, because I knew that “the squeaky wheel gets the grease.”

That’s my mom’s favorite American proverb—notable in a household rife with such colorful French sayings as “take care of your onions” and “I have other cats to whip.” She encouraged me to squeak up as a way of life, and it turned out to be a pretty useful attitude when I got into the art business. If I’d been more self-aware at the time, I might have told my friend that my first real break was my mom.

A few years later, another important opportunity came in the form of my art becoming embroiled in a political scandal in Portland, Oregon.

Back in 2005, I’d painted a number of local public officials, and in 2008 I participated in a show at City Hall, where I thought it would be fun to hang some of that work. During that exhibition, one of the City Commissioners’ offices approached me about buying his portrait, suggesting the price should be $750 instead of the $1000 I was asking. I wasn’t thrilled to be bargained down, but I accepted the offer. When I received the check a while later, I was surprised to see it came not from the Commissioner’s private account but from his campaign fund. Needing the money for rent, I didn’t feel empowered to squeak up about it, choosing instead to cash the check and assume the Commissioner knew what he was doing.

A few months later, the dragging in the papers began, including the article shown above. The press focused on the Commissioner’s questionable ethics, but they also rolled around a bit in the muck of “isn’t art the most ridiculous thing to spend money on?” And that choice to treat art with contempt opened the door for Commissioner Shady to say some pretty rude things about my painting.

Which leads me to the big break of it all: in this case, the opportunity wasn’t in the coverage itself. Rather, it was the relatively controlled exposure to bad press that turned out to be important, because it allowed me to learn how to respond when I wasn’t the main target of the public’s ire. Years later, when my own ethics were impugned in Newsweek and I had to figure out how to weather that hit to my artistic reputation, I was grateful to have been through a trial run.

Of course, I couldn’t have known all that back in 2008.

That’s the thing about the truly big breaks. They’re not usually the accomplishments you include in your press kit, because they’re not the fancy exhibit in a fashionable gallery or the feature on a popular site.

They’re the opportunities you maybe don’t even recognize in the moment—the chance of your birth and who your parents are or the unpleasant experience that prepares you for a positively nightmarish one down the road.

Big breaks don’t come from a universe that’s decided to make you a star: they come from luck and, more importantly, from a concerted effort to notice all the good fortune you already have.