shadow career writing making money

Making Good Money… in a Shadow Career

Chapter nine in a series on Book and Art Business 101 wherein I show how the solid logic of art business sold me on self-publishing. If you’re too busy for the whole series, download your copy of my Cheat Sheet for Book and Art Business 101. 

Once you’ve read The Writer’s Market and come to terms with the good sides of your gift, once you’ve started putting down your daydreams on paper and decided to work regularly of your own volition, once you’ve reformed your craft through that self-assessment called “rejection,” you’ll figure out how to make good money.

In many inferior ways.

You’ll figure out what it’s like to be making good money in a shadow career.

Remember when in the Where and How to Sell What You Write section when I told you that tons of people out there want to make money off of you, the writer, and don’t necessarily have your best interests at heart?

Remember when in the Any Money Makes a Pro section when I told you that making passive income will help you create the space you need to start making money off of your writing?

And remember when in the Quarterly Assignments section where I told you that regular work is a double-edged sword? How it can lull you into passivity?

Well smash all of that together and you’ll get the shadow career.

You can make good money off of people who want to make money off of you, people who are offering you passive income or the space you need to make money writing, people who want to give you very regular work.

It’s called advertising.

Chesterton taught us in Utopia of Usurers that in a modern capitalistic society it’s not that there won’t be any good art. It’s that there won’t be any art that is not simultaneously advertisement and that’s a considerable step lower. Spiderman can’t shoot a web without shooting at a Dr. Pepper can. The Transformers can’t show up on screen unless they’re the most recent model of the Dodge Charger. Half the clichés Americans use didn’t originate with poets as they did in other cultures. They originated with copywriters — anyone who watched the first episode of Mad Men knows this. But anyone who has watched Mad Men also knows that all of those boys have a manuscript in the bottom draw of their desk or a painting at home or a dream to be a movie star.

You can make a lot of money selling someone else’s work. Is that what you want?

If it is, be the best salesman in the world. But very, very few people show up to career day in gradeschool saying, “When I grow up, I want to have higher sales figures than Dale Carnegy and Zig Ziglar combined.” Warren Buffett didn’t even think that, exactly. He was too busy learning about class ranking for horses and reinvesting his profits for compounded interest.

My guess is that someone so burned you early on, so drilled into your head that you can’t make money writing that you got desperate and tried to short circuit the process. I did. I was burned by a great many people I respect and started making a lot of money doing something that resembled fiction writing on the outside but was very, very far from my goal. I would have been better staying at the hospital, in the end, because I ended up taking a five-year detour around my goal. I wrote copy for ad agencies and tech startups. I poured hours over phrases that sold umbrella insurance, only to have to (1) deliver it on spec — meaning working for free — and (2) have super needy clients change it to a lesser campaign anyways.

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For what?

To make money writing.

I told you: I was desperate. Warren Buffett said, “I chose early on to only work for people I respect and the only person I respect is me.” I had something of that attitude in me early on, but I’ve gotten rid of it — there are several people I’d happily work for or alongside these days. I’m no longer desperate. And because I’m no longer desperate, I’m doing a lot better work, quicker, and for much higher returns.

And it’s all my own work. Work I care about. I’m not selling my birthright for a bowl of soup.

In this city, everyone’s something else. My business partner Kyle Welch said, “New York is a city of underachieving geniuses. L.A. is a city of overachieving morons.” I know what he means. In L.A., you meet guys that made millions off of cat posters so that they can surf all day long. In New York, you’ll be grinding it out as an extra on the set of some Netflix TV series alongside a guy who just wrote the next great American opera, a guy who has no connections and no hope and is just struggling along. “Starving artist” is used as a term of insult in America but Mother Theresa often starved that the lepers she loved might eat. Perhaps the artist has an eye for more than the next ten years. Perhaps the artist, like Fred Danback, has his eye on his great-great-great grandchildren.

Here, people will also make millions in finance or advertising or real estate because it’s the closest thing they could get to the thing they love and they went from survival to survival of the fittest quicker than a cheetah kill. Think about that. Is that you? Did you go from survival mode to survival of the fittest mode?

Did you go from being a starving artist to the kind of person who profits off of making artists starve?

Shame on you.

Shame on me.

Shame on all of us for accepting this as normal. It’s not normal. It’s distinctly American, but not everything distinctly American is distinctly good — like Japanese internment camps and African slavery and legalized usury that results in political bribery. It’s unacceptable that we convert our brightest minds and best hope for tomorrow into people who exploit those with the brightest minds and best hopes. I reject my shadow careers and embrace my real, my true, my überself — the man I was made to be.

You too.

Become you-i-er. Today. Right now.

Stop making money off of that shadow career. I’d rather you work in a field completely unrelated to your writing (or art), a field that can give you space to write or create than for you to compromise your vision and passion, sacrificing it all to that golden calf on Wall.


It’s going to be okay, I promise. Hang with me.

Oh and by the way, that golden calf on Wall? It was originally an installation made by an artist to critique American greed and celebrate the strength and power of the American people. It took guts, a vision for the future, and passion to convey such a message in the heart of such a place. That Wall Street embraced the golden calf as their go-to mascot tells you everything you need to know.

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And that’s coming from a Taurus.

Don’t have time for the whole series?

That’s okay, I made you a…


Here’s our outline for upcoming posts:

  1. Intro
  2. The Gateway Drug: Poetry
  3. Does Fiction Lie? — The Liar’s Club
  4. Where and How to Sell What You Write
  5. From Daydreams to Written Dreams
  6. Rejection Slips
  7. Any Money Makes a Professional Writer
  8. Regular Writing Assignments
  9. Making Good Money… in a shadow career
  10. Kinfolk and Advocates or “How to Build a Platform”
  11. Draconian Contracts
  12. Author Earnings
  13. Succeeding for Others
  14. Blaze a Trail All Your Own

lancelot tobias mearcstapa schaubert monogram

cover image from U.S. Geological Survey

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