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Writing and drawings about work, family and the stuff in-between

Why a shadow career might get me to my dream job


Ever since I heard about the notion of a shadow career I’ve been haunted by it. My current “career” consists of helping artists, writers, and many others make money as professionals, and as an artist myself, I often feel envy when I imagine how great it would be to draw and write for a living. Am I just too scared to try it? Yes and no. The more I’ve thought about it the more I think I’m right where I should be. My shadow career can make my dream career possible.

The concept of a shadow career comes from Steven Pressfield’s (great) little book Turning Pro.

Here is an excerpt:

Sometimes, when we’re terrified of embracing our true calling, we’ll pursue a shadow calling instead. The shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.

Are you pursuing a shadow career?

Are you getting your Ph.D. in Elizabethan Studies because you’re afraid to write the tragedies and comedies you know you have inside you? Are you living the drugs-and-booze half of the musician’s life, without actually writing the music? Are you working in a support capacity for an innovator because you’re afraid to risk being an innovator yourself?

Dang, this got me thinking hard about what I’m doing with my current career. I love the work that I do as a support (aka Happiness) engineer with WordPress.com. I get to help artists, craftsman, coaches, authors, and the occasional spirit guide showcase their creativity, sell their work, and realize their dreams.

Should I be on the other side of that? Should I be pursuing my own artistic thing rather than supporting someone else’s?

Steven Pressfield says I should be. I need to turn pro dammit!

I’ve spent the better part of the year thinking that the only way I’m going to be able to do this is to go all in, completely, and say “fuck it, I’m doing this art thing full-time”. Losing the safety net of having a “day job” was going to be the only thing that would push me to really do it, I thought.

I haven’t done it though, and I think that’s because deep down I know it would be a terrible idea, at least right now. I’ve got a family to support. I can’t burn all the ships.

If Steven Pressfield and I were buds, he might call me and tell me that duty to family, and any other reasons I might drag up, are really just my fear of failing stopping me and that this is “The Resistance” keeping me from my calling.

I don’t think so.

In How to do what you love and make good money, which is part of Derek Siver’s (great) little book Hell Yeah or No, Siver says that the happiest people he knows have both a stable job and a dream job.

The stable job is done for money and security. The dream job is not done for money (since none is needed) it is done for expression. The head and the heart work together to create a balance.

Each half of your life becomes a remedy for the other. You get paid stability for part of your day, but then need creative time for expression. So you push yourself creatively, expose your vulnerable art to the public, feel the frustration of rejection and apathy, and then long for some stability again. Each half is a remedy for the other.

I referred to the dream job as a job, though, not a hobby or a side project. This is the key. They must both be treated as equally serious pursuits and approached with the same consistency and discipline as any craft would be.

Here is how Siver explains it:

About your art: Pursue it seriously. Take lessons. Make weekly progress. Keep improving, even if you’ve been doing it for decades.

If you don’t progress and challenge yourself creatively, it won’t satisfy the balance. Release and sell your work like a professional. Find some fans. Let them pay you. But your attitude is different than someone who needs the money. You don’t need to worry if it doesn’t sell. (…) Most full-time artists I know only spend an hour or two a day actually doing their art. The rest is spent on the boring work that comes with trying to make it a full-time career. So skip the art career and just do the art.

I don’t need to burn all the ships, I need to start building some more.

For one, I could start my dream job by just be being more organized and disciplined (I am pretty good at that) and carving out my best hour of the day to my new job. Second, I haven’t really developed or progressed the quality of my art in many years, so I could use that hour to pursue training from those doing the job better than me (which includes a massive list of almost every artist online). Third, my current job is teaching me all about how to make money as an artist, so I actually am getting one of the parts of my training by doing what I’m doing and I can keep doing that seriously.

The dream job is there for me whenever I want to start it. I think Steven would approve.

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