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My countless talks at art schools are having an unexpected effect. I’m reflecting more on the jobs I held prior to blogging and how those experiences taught me to create the work I wanted. It took close to six years of wrongful employment with all sorts of crazies to figure out what I would be doing in my thirties, which seems like a lot, but I count myself lucky, especially since many people never figure it out. I spent a lot of money on art school and the idea of repurposing those skills for my parents’ farm has never been particularly appealing.

The first job I proved ill-suited for was teaching inner-city kids how to paint their school walls. The non-profit tasked employees and children living in underprivileged neighborhoods with beautifying their schools. It was a tough job, and frankly most of us involved weren’t the ones to do it. Many of the kids didn’t want to be there, and neither did I. My painting groups consistently covered the smallest area in the schools, and when I told my boss I knew I had a lot left to do, we ended up talking about other lines of work I could get into. Needless to say, that was the end of that job.

I wasn’t happy that my three-week paid stint at the school didn’t work out, but I tried to rationalize the failure as irrelevant. I was going to be an artist anyway, so what did it matter? This aspiration was probably why my dead-end job framing prints at the New York Library suited me so well. There were about eight artists on staff to complete a three-person task, so for the most part we spent our days playing cards and talking about art. It was probably my favorite New York City job because I found our daily conversations and yucking so fulfilling. Not surprisingly though, when my work visa (I’m a Canadian) expired, the library didn’t bother to renew it.

I was devastated when the job ended, and felt lost for years. I loved talking about art and couldn’t conceive of another attainable job in which “yucking it up” was the description. During the time in between working at the library and starting my blog, I managed to cobble together work from whomever would agree to employ me under a dubiously legal TN-1 visa as a graphic designer. I say “dubiously legal” because I was never actually employed to do that job. Mostly I worked for a string of crazy dealers as an administrative assistant, colloquially known as a gallerina. I’m not very organized, which made the job a bit of a challenge, as did my complete disinterest in working on anyone else’s projects. This wasn’t self-interest and narcissism as much as insecurity: How was I supposed to guess what other people wanted or needed?

It was mostly my inability to deal with difficult personalities though that got me canned from these jobs. I attracted bullying. The number of low moments I had during this time are almost too many to count: The dealer who rolled her eyes in disgust at me when I told her I was the only one of her assistants around to pick up a piece of food a client had dropped on the floor; the woman who yelled at me because her sick dog had pissed all over my shoes; the gallerist so convinced I was unable to make a proper measurement that she forced the framer to come in and do the job for me while I watched. This abuse left me believing I was incompetent, and I saw little way out. My visa limited the kinds of jobs I could take and fear of having to return home to the farm kept me working until I was fired.

I started a blog mostly out of misery. The first writing I did was on a now-deleted personal site, where I dedicated a large number of posts to joking about random experiences I’d had. It was only through the constant nagging of a friend outside the art world that I took on Art Fag City, authoring it anonymously at first. I naively believed I could turn the art world upside down with my “insider” knowledge. It didn’t occur to me that not having any would challenge this plan, which is why it took less than three months to reveal my identity—I couldn’t get enough links or quotes without it.

Stressed out, unemployed and broke, this decision marked a turning point in my career, even it I didn’t recognize it at first: I was happy again. To write well I had to become more active within the art community, which meant chatting with a lot of people. This was the same reality as the library job, though the group was smaller, and the activity unsustainable. Of course, my blog’s viability is up in the air today too—I don’t even make enough money to afford health insurance—but I get so much out of the conversations it hosts, I have no interest in giving it up. There’s nothing more fulfilling than talking about art.