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“A fool and his money are lucky enough to get together in the first place.” Wall Street

I’m lucky enough that I can say first-hand that it’s true, if you do what you love you’ll never have to work a day in your life. Stick me in front of any old word processing program, notebook, whiteboard, paper napkin and give me something to write with, I’m happy. More than happy, I’m at ease more so than I am when I’m not writing. It’s weird.

The first paycheck I got for putting my cursor to work was back in 2000. The entire experience made me laugh, and not just because I knew, at the ripe age of nineteen, that I was being drastically underpaid, but because I had done nothing that made me feel as though I deserved an iota of monetary compensation. I sat down, I wrote about the topic I was instructed to, and a middle-aged editor in a loft overlooking Houston Street cut me a check. It was like I played the biggest joke on the world. It felt like a bank heist. I probably bought a tattoo with the money.

Fast forward eight years and slide a few bills under the door. I can’t call up T-Mobile and say, “Hey there! Don’t you just love allowing people to communicate? You do? Well, then look at that as my payment for your service. Your happiness.”

Not so much. However, it seems to be common practice in the world of freelance writing that your clients often won’t see the importance in paying you. They may openly gush about your work, they may refer you to their friends, they may say that your business card is the most creative and hilarious thing they’ve seen since Blue Man Group (seriously, that’s how dated most people who would hire me are) but ask for payment and you get…crickets.

I had a deadline today. I handed in my work on Friday (yes, early), went through the text with the client, sent in revisions. Sent two follow-up emails. Suddenly I‘m being avoided in a more severe way than the time in high-school when I wouldn‘t let Danny Lynch have sex with me in the backseat of my cousin‘s Civic. This cold shoulder would be fine, if it were a cold shoulder of beef I could carve up and eat. Unfortunately it’s not.

Tomorrow I’m going to have to call the gentleman and I can nearly guarantee what’s going to happen: he’s not going to answer. Or, if he has forgotten the only cell-phone number from Nassau County in this little town belongs to yours truly, he may pick up and be suddenly, inexplicably busy. But chances are that I sent the assignment off into the ether like Apollo 13, except instead of getting a heroic ending in the form of a deposit slip I’m getting a personal tragedy. That was my cell-phone bill and part of my rent, motherfucker.

My mentor, who is phenomenally successful and a bitch enough to be otherworldly attractive too, has told me to demand “at least thirty percent up-front.” I have now learned the hard way that this is more than crucial, it’s quite simply shitty business not to. And it reflects having the self-esteem of an overweight sixth grade girl going straight from the orthodontists’ office to a beauty pageant. I love to write, but not asking for at least some money immediately upon being hired just comes across as desperate. And stupid.

You’d think that I would have learned by now. You’d think I would have applied my east coast I’ll-cut-a-bitch-with-no-questions-asked mentality to work. But it seems that karma might be kicking my ass. I remember telling my paranoid pilates boss that she didn’t give her customers the benefit of the doubt. They would pay. If they said they forgot their wallet at home and that they’d pay next time then chances are they, you know, forgot their wallet. They’d pay next time. They weren’t out to get her.

I wonder what she’d have to say about this little predicament I find myself in. Two hundred dollars worth of work and I can’t get my client to respond to me, even just to man-up and say he’s not paying for whatever reason. (“I don’t want to” would even work in this instance because at least then one person would be triumphing over the Portland non-confrontational flakiness I see nearly every day on line at the nearest Stumptown.)

Simon is a copywriter as well. I could spout praise about him all over this blog but instead I’ll just say that if you’re interested in reading some insanely good writing go here. He is also fiercely intelligent, witty as hell, and hotter than a Scotch Bonnet. (Sorry, ladies. I aimed my blowdart gun expertly in this case.) But when it comes to business he’s gone through this not once, not twice, but three times, each lack of a paycheck accompanied by my tongue clucking, saying, “You know, you really need to start asking for them to pay you before you send out the work.”

Now that he’s taken me on as his business partner we’ve had to strategize and try to figure out a way to get the cash for the characters, the paychecks for the paragraphs, the Washingtons for the words. (Okay, bigger than Washingtons. We hope.) So far my list includes “call their mothers,” “cry,” and the not-so-business-savvy “hire someone large to threaten them, possibly with angry dogs.” I also thought “protest” but realized that this is Portland and a) it’s impossible to make anybody show up on time for anything and b) there are too many fucking protests.

So here’s the outcome, before we starve to death, I would like a list of suggestions.
If you have any – the ridiculous, the serious, the ones that have worked for you – please email me at

ainsleydrew at gee male dot calm.



One Comment

  1. The idea that Rowlings wouldn’t be paid for book one of seven is absurd. Sell a serial a piece at a time.

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