Question: When should I get an accountant to help deal with my freelance income?

Money is weird. Our brains really aren’t built for dealing with it, because our minds actually haven’t adapted that much from our days running away from tigers and hunting for berries to gorge on. We’re good at thinking about lunch, or about our chances of catching the bus if we leave right now. We think linearly—one thing after the other. Money isn’t linear, though. Money grows and shrinks exponentially.

That part was hard; there was a learning curve. My uncle is an accountant and he was handling my taxes. I learned Quickbooks while I was working for Mary Meyer. I also have a lot of spreadsheets. I think if you’re running a creative business you have to be aware of the fact that you’re not going to be doing creative stuff most of the time. Mostly you’re going to be e-mailing people.

I needed somebody to help me with money because I’m the worst. I don’t know how much to charge. Probably a lot of people are like that, but for me that’s where I get screwed up. The problem is, I don’t fit into a slot very well.

A gallery will typically send you a check or wire transfer. Do not expect a 1099 form come tax season—as an artist you’re providing a good, not a service, and therefore don’t need a 1099. As always, it’s a good idea to keep a record of your payment history.

At certain points in my career I would spend up to 80% of my time fundraising. Lots of organizations spend up to 90% of their time fundraising. It’s like a Senator when they get back in office, they then have to raise X number of dollars every day in order to keep things going. It’s no joke. For artists, it can feel just the same.

That’s the thing about being creative: You’re trying to make money off of something so deep. It can be really scary.