What my weirdest job taught me about the outsider wound

Week 21: The Brilliance Experiment

Welcome to The Brilliance Experiment, a 52-week reclamation of the magic that gets lost in the difficult times.

This week I’m sharing what my weirdest gig as an entrepreneur taught me about surrender, the $4 purchase that’s got me making art again, how I’m using IFS to eradicate the starving artist mentality, we’re starting Big Magic Book Club this week.

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“I’m going freelance!” I told my sister over the phone.

“To do… what?” she asked in equal parts confusion and judgment.

“Well, art! And business stuff. I don’t know… I’ll figure it out. I just think I can make a better life for myself piecing things together instead of getting fired or laid off every couple of years.”

I was lost and tired when I made that decision five years ago. I wanted to work for myself because I thought it would give me more control. And in some ways, it has! But in other ways, I feel like someone who knows too much now.

I’m constantly playing tug-of-war between knowing I was never built for the corporate grind, but craving the fragile sense of stability it provides.

To keep the lights on, I’ve done a lot of odd, sometimes very humbling jobs. I’m learning to accept that this is just part of the creative path. There are seasons when you really have to search for the silver linings just to keep your head up.

I don’t speak about it often, because I’m a little embarrassed that I still have to do odd jobs to make ends meet sometimes. But that doesn’t help me or you at all, so let’s talk about it.