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As a freelance writer, you’re often required to write an inquiry letter, or cover letter, that you submit with your samples and resume. This letter is to be classy and original, witty without being glib, a brief showcase of all your good traits, with a come hither final line that seals the proverbial deal. In short, it’s, like, the most difficult thing to write, like, ever.

In my professional experience I’ve had to pen my fair share of cover letters, usually for administrative assistant positions. I’ve followed a formula that I was taught early on, and I’ve always relied on my ability to isolate details, about myself and the desired position, that play well together. Often this is reflexively helpful, if I find myself stumped for a reason as to why or how I’d be good for the position it’s often a sign that I shouldn’t bother to apply.

Being raised by a woman who, for whatever unknown reason, wanted to install in her only child a set of rigid and dated manners along with a fear of authority reminiscent of the musical Les Mis, I have weird and extreme etiquette. I basically assume I am everybody’s humble servant and, just short of curtsying, I will treat you like you own me…for the first five minutes I meet you. After that, unless it’s an actual job interview, the “fucks,” “cunts,” and garden-variety vagina jokes come out.

After an ex-girlfriend’s mother berated me, violently, for calling her Mrs. Ex-Girlfriend’s Last Name, I’ve become a bit more world weary and less inclined to manner my way to the throne.

What does this have to do with cover letters? Everything. The usual rigmarole, for me at least, is a semi-formal affair. While it’s no black tie ball — I don’t use conventional business letter formatting or, yikes, snail mail — I do speak to the recipient as though they are, say, Tony Blair. Or God. It’s nothing, if not professional.

But what about the boutique company, the small seven-person firm looking for a writer, the quirky and down-to-earth client who will hire you more for your personality than for your ability to wear a skirt suit and heels? Those jobs require an important and incredibly difficult part of the freelance repertoire: the colloquial cover letter.

I imagine this sort of tonal dissonance is encountered by adults writing PSAs for teens, or writers for Spin magazine when they interview a semi-famous band. (“Bro, do you think open source media is lame or rad?”) It’s a strange note to try to hit, the one between reverent and, well, irreverent. Here are the three key points that I have discovered that I can share with those of you looking to kick back, relax, and cobble together the informal letter that gets you hired. Just remember to send me a cut of your first paycheck.

One: It Is Still Like Football

That is to say, you should outline your course of action before writing the thing. As most high-school graduates have learned when they were taught how to construct a solid five paragraph essay, building the skeleton of key points prior to fleshing out the text is the best way to keep any sort of text concise, hard-hitting, and wholly on track. Otherwise you wind up being long winded, and the only job that being too talky guarantees you is to go and pick up somebody’s dry cleaning. Or maybe that’s just me.

Two: This Is Not Facebook

It is tempting to use the informal inquiry to showcase how spectacularly funny and hip you are. After all, you can write on the cutting edge, why not prove it? The answer is because this is a job, not a popularity contest.

Often as I was starting out freelancing I tried to prove my unequivocal greatness by submitting too much, an onslaught of samples coupled with letters that, in hindsight, came across as pompous and condescending. Of course that hadn’t been my intent, it’s just that, naturally, I felt insecure about the hiring process, so I tried to overcompensate. What I thought came across as phenomenally cool and revealing actually was overbearing and masturbatory. You wouldn’t masturbate in a job interview, would you? (If you answered yes I am hiring.)

The cover letter is a lot like a first date. You want to tell them a little bit about how great you are, but no need to harp on your ex-girlfriend, or what kinky bedroom games you’re interested in playing. Less is more, especially if that less is awesome.

Three: Profread.

Ha. Get it?

My fatal flaw (other than my insatiable sex drive and the fact that I’m a sushi-loving vegan) is editing my own work. I’ve gotten better at it, thanks mainly to Simon, who has the opposite problem of never feeling fully finished with a piece of work due to an addiction to scrutiny. I cannot stress enough how, in an informal letter especially, it is vital to make sure you’ve used proper grammar, perfect spelling, and on-point punctuation. When you’re employing a less fancy method of conveying how talented and capable you are, the last thing you want it to sound like is a fifteen year old girl’s text message from the mall. U r g8, yes, but make sure your future employer knows that you understand business syntax, too.

There are other tiny nuggets of wisdom: use a comma, not a colon after your introduction, use contractions to make the tone more easygoing, feel free to write “Dear” in place of “To Whom It May Concern,” and don’t shy away from brief personal statements. Basic stuff that seems like common sense.

Of course, you can write all of this advice off because I’m barely able to pay my rent this month, and I’m hoping that this guidance translates to my own professional success in the coming weeks.

If I don’t hear back I’ll let you know it’s bunk, and write a post on how to write the perfect desperate one-sentence plea that can be scribed in Sharpie on a piece of cardboard.

I’m grateful to everyone who reads this, but especially to you crazy kids who donate. It means a lot and it keeps me fed. (And sheltered, this month.) AinsleyDrew at gmail, because I have no hobbies other than this blog I will most certainly write you back.

Will Work For Food.

What I’m doing when I’m not doing work.


One Comment

  1. I’ve previously recommended this technique to others and have been amazed at the positive response I’ve received. So here goes nothing.

    When you proofread your stuff, read it backwards, one word at a time. This has the effect of tricking your mind into seeing what is actually on the page (or screen) instead of what it would otherwise think is there. When you’re proofing your own work, the tendency is to read what was in your mind when you wrote it, rather than what actually made it onto the page, and even goes so far as to notice when you used then instead of than or something else that a spellchecker is going to miss.

    Anyway, hope it helps.

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