How Freelance Writers $pend Money

Matt Gross
3 min readMar 24, 2017

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Surprise! The system makes it really hard to be financially responsible.

How I feel when a story gets assigned.

Over the past 15 or so years, I’ve mostly been a freelance writer. At times, I’ve had a ton of assignments, each one following from the last, and at others they’ve merely trickled in. I’ve had staff jobs, too, where the checks arrived every two weeks without fail (pretty much). Since February, I’ve been back on the freelance circuit, and I’ve noticed a problem I’d never quite identified before.

The problem is this:

  1. I pitch a story, and if the editor picks it up, I’m psyched. I’ll have money coming in! That means I can spend some of it now, maybe on a chunk of good cheese that I wouldn’t ordinarily buy, or on a season of a TV show I have no business watching. It’s okay, though, because I’ve just set myself up to earn money.
  2. I report, write, and file the story. Whew! That was an effort, but my filing the story now guarantees that I’ll get paid. So it’s okay to spend a bit more money right now, like on a set of graphic novels for Sasha or a cocktail at a bar while I write a piece on Medium for which I’ll earn nothing. But it’s okay, because the money is coming in real soon.
  3. A couple of days later, I remember I forgot to invoice properly. So I do that. And buy the aged, grass-fed ribeye instead of the industrial hanger steak.
  4. Anywhere between 7 days and 2 months later, the check appears in the mail! (Or, even better, the money is direct-deposited into my bank account.) Hallelujah! Now I actually have the money I’ve earned, and I can spend against it. Shit, should I upgrade my MacBook Air? I mean, it’s nearly three and a half years old!

So, yeah, I hope you can see the issue: At each stage of the freelance-writing process, I spend money I don’t yet have. Clearly, I should be a bit more conservative with my income—I don’t need that Vermont camembert, do I? And honestly, I’m not quite so spendthrift as I’ve made out here. I eat lunch at home (usually), and I almost never buy the fancy cheese, and I haven’t spent a dime on technology since last September (and the nice headphones were on sale, thank you very much). I was, you may recall, professionally frugal not all that long ago, and those instincts have not completely evaporated.

Still, I’m frustrated at the cycle I feel locked into. I want to reward myself for meeting milestones, since paydays for freelancers can seem impossibly distant otherwise. But it also feels sort of sick, always mentally borrowing against what I expect to happen.

There is, however, a clear and obvious solution. Editors: Pay me as soon as you accept the pitch. You’ll save us all a ton of heartache and consternation, and I’ll be able to purchase that triple-crème with a clear conscience. And don’t worry, don’t worry. I’ll make my deadlines just fine, even if I have to hole up in a bar while Sasha’s at ballet class to write a really, really awesome kicker.

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Matt Gross

Restless & hungry. Writing about travel, food, parenting, and culture all over the place.