regular writing assignments steam engine train

Regular Writing Assignments — The Dark and The Light

Chapter eight 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 the rejections slow down and you’ve found a bit of success (or, possibly, a bit of success has found you), something even more dangerous can set in and throw off your internal compass, reneging scores on your internal scorecard.

It’s the danger of regular work, regular writing assignments.

Work you can count on.

Over the years, a several different publications and businesses have given me assignments that came in quarterly or monthly. It was steady work, the kind of regular contract any businessman should seek. Long-term buy-and-hold investors often look for undervalued dividend-paying stocks. This is the literary equivalent of the quarterly dividend. But there’s a deeper layer to the metaphor:

Sometimes a stock is being artificially propped up by share repurchases and by giving out a larger and larger share of their earnings to shareholders as dividends. The executive board is doing this because they’re lost. They don’t know how to reinvest earnings into their own company to exponentially increase their future return and thus enrich shareholders. A quarterly assignment can do this to the author.

You get to where you count on that paycheck. You get to where you expect it. You get to where you don’t write another short story because this one, this one, is guaranteed to give you another writing credit and challenge you to produce regularly.

But is regularity enough at this stage in the game?

Surely by this stage in the game, you’ve taught yourself good habits and are writing daily. So regular assignments won’t help you that much in that department. Which means you need to be evaluating this assignment based on (1) how it stretches you to grow creatively and in terms of honing your craft as well as (2) the momentum of reinvesting the earnings you make from these sales. I was noticing, for instance, that I had gone from making a habit of being way early on one of my quarterly assignments to making a habit of being way late delivering on deadline.


What had changed?

The money certainly hadn’t changed: I’d been reinvesting my profits in a couple of productivity tools and platform building resources. When those tools ran out, I was saving up to reinvest in marketing, an assistant, and a bulk buy of some shares of stock that related to the literary business. Rule #1 is always reinvest your profits to compound the effect your money has and make it work as hard as possible for you. The money, in other words, generates as much momentum as time or mass if allowed to compound.

But that wasn’t enough. I felt, in my bones, that my time could be spent making more money doing bigger projects over the long hall. I was still delivering late. What else was wrong?

Here’s what was wrong:

The assignment no longer challenged me. I had gotten to the point where I would spend a half hour on a draft and email it immediately. It would go to publication with minor blue pencil adjustments, published almost as-is. An artist who has worked himself beyond criticism isn’t an artist anymore because art is always a dialog between the maker and the spectator, the giver and the receiver. You and I? We’re not God. That means we’re not perfect or good through-and-through. We’re flawed.

READ NEXT:  War for Your Mind: Information in 2016

We need reform, regular changes of mind, adaptation, evolution.

And when we’re a member of a broader society — civil, literary, or otherwise?


That can’t happen if you’ve worked yourself into a very clean, very safe, very well-preserved museum exhibit. Art thrives when it looks a bit lived-in — the billionaire grandma who never allows her grandkids to write on her white walls is missing an essential part of what it means to be a grandma. And, as a matter of fact, what it means to raise up the next generation of writers.

So I quit.

And the editor, who has worked with me for years, wished me a ton of luck and understood completely — she’d been feeling it too, I’m sure. If there’s one thing an editor hates, it’s late writers.

To review: the benefit of a quarterly assignment is steady income that you can consistently reinvest as if it were a DRIP (dividend re-investment program) for a utility stock.

The downside is malaise: never get comfortable in your writing. Never get to where you’re writing fiction free from critique and the reformation of rejection. I want you to succeed, but not that easily: if it comes between your success and your greatness, choose the latter. The path of least resistance is not the path of the high and noble, the way of the knight. Choose renown over fame, investiture over fortune, meekness over power, long suffering over instant gratification, and faithfulness in your craft over get rich quick schemes.

Steady work, in short, is great.

But you must be the initiator of that steady work. Otherwise you’re only doing it because someone else is nagging. And writing because someone’s nagging is worse than doing the dishes because someone’s nagging. At least with the dishes someone has to do it. No one has to write. To put yourself in a position where you feel that way is ludicrous.

Regular writing assignments may count as your regular, willful work, but often they can get in the way.

But not always, so:


  1. Work daily at will.
  2. And then reinvest the profits that come from your regular, willful work.

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 Chris Devers

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