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I’m a firm believer in dating. Before I was wooed by my boy’s love-letters I was all for knocking boots with ladies and gentlemen NSA (“no strings attached,” for all you monks and cat ladies out there.) My feeling has always been that dating is a nuanced gerund. You can date several people at once, not all of the same gender, and not all for the same reasons. Short-term relationships can boost self-esteem, add zest to an otherwise dull social scene, and help an individual figure out what they want in a long-term partner, or if they want a long-term partner at all.

Of course dating many people can put you at risk of all kinds of STDs and STIs, too. Every rose has its thorn, and every rotating panty Rolodex has its herpes. Be careful out there.

martin b

What the hell does this have to do with looking for work, you ask? No, I’m not once again toying with the idea of becoming an escort. I’m addressing the most important quickie of them all: the client.


This morning it dawned on me that I’ll probably always be looking for work. Even if I have enough money and no longer have to worry about this month’s rent or tomorrow’s bag of Goldfish crackers, I’ll perpetually be hunting, searching for the next gig. Like the pioneer Paleolithic lady who was already envisioning her spear in the next prehistoric rabbit while chowing down on her most recent kill, I’m always going to be trying to figure out where my next meal is coming from.

Lost World

So does a freelancer look for a wife or a trollop? Do you want a long-term union or a brief and feverish relationship that ends once the second check has cleared? In this wilderness do you look for the pack of bison, even if it means abandoning that lone and sickly armadillo that has wandered in your path? (Okay, so my dating and cavemen rhetorical tropes are convoluted, and my prehistoric landscape strongly resembles a Busch Gardens safari. At least I’m not referencing Quest for Fire, or worse, Geico.)

Prehistoric Women

We have one client who hired us for a month-long gig, but other than that there have been a smattering of assorted, random single assignments that range in subject matter from companies selling automotive parts to vodka advertisements to success stories on software networking solutions. While this has been great for testing our range as writers, once that job is completed I’m back out on the cyber pavement, leaning into the passenger side window, hoping that this one will cover a little bit more of the cellphone bill.

Does pursuing a client who would hire writers for a regular gig — say corporate blogging or events listings on a website — differ from just poaching for any old job that comes along? How does marketing yourself as a company that can provide for the long-haul vary from saying that you are Mr. and Ms. Right Now?

If only it were as simple as saying you’re very good at ironing, go to Church on Sundays, and bake a mean apple pie. Of course, in that case we’d still be pretty fucked, though I will humbly let you know that my apple pie is absolutely awesome.


Moreover, if you take on those regular gigs, I wonder if it’s easy to become pigeonholed and stagnant. A two-year long gig writing for a butcher shop might make you an master of meat, but it may also work directly against the possibility of writing the press release for the new Cherished Chinchillas petting zoo.

Also, I suppose this whole rumination is rendered moot since I’m having enough difficulty wrangling clients in general. Although we’re versatile, eager, and talented enough that we shouldn’t be this desperate, I find my perspective seemingly identical to a woman with a cat and no suitors approaching her forties. I need clients, any clients, to fill my desire for experience just as much as I need to fill my pantry. But if I could find a few steady, select gigs to ensure that there’s always at least a little work coming in, well, I’d settle for writing within the same genre at least part of the time.


Relationships are about compromise, both in the bedroom and the boardroom. (Or, in our case, in the coffeeshop with WiFi.) I just want to know if I should be taking every job I see or if that will negate any possibility of settling down one day. Perhaps freelancing means that no matter what you’re always going to be a bit of a slut, at least when it comes to work.

ainsleydrew at gmail

fit it in there



  1. I’ve always taken the first offer, usually not even waiting a few days to see if a better offer might appear. I’ve always assumed that it makes me a slut, even if the gigs average 18 months. For 15 years, i’ve been a contractor. But it doesn’t matter, my average was 18 months when it was direct hire. The pay is about the same. I wanted to be able to opt out of health insurance, since my spouse had the best plan i was likely to get anywhere. I don’t have that anymore, so it really doesn’t matter.

  2. Not that I have any experience at the freelancing thing, but having studied it for a little while now (and having worked closely with a number of consultants over the years), so now I’m an outspoken expert on it. In other words, take my advice with a grain of salt.

    I’d say that the best tack to take is to line up as many as you can. Look for what you can get right now (long, short, periodic [like recurring cover notes for a local music production company, maybe?], blowjob, handjob, rimjob, ANYJOB), and book little jobs over one another. Hell, book little jobs over everything, and bloat your timelines (this is fairly good practice anyway for one never knows when writers’ block may arise…nor when the ants might rise up against their cinnabun-crotched oppressor). There will be times when your client won’t be able to deal with that, but if you tell them you’d rather they go somewhere else than deliver them a half-ass job, they’ll be more likely to remember you for respecting the quality of your work enough to not back down (and you might even find that the hard date they gave you isn’t as etched in stone as initially advertised). Be willing to let them go, though. They’ll respect you in the morning if you turn them away.

    While you’re trying to keep from drowning in the biblical flood of work you have, build a brand for yourself and market yourself like rabbits fuck: a LOT. (I highly recommend Seth Godin for inspiration/direction in the branding and marketing endeavor.)

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