Here’s all the great advice I found about writing cover letters

Sebastien Wiertz/Flickr


It’s application season for those of us who want to seriously pursue writing and/but are terrifyingly late in our college careers.

I spent the last couple days making a list of places that, probably won’t, but maybe-in-a-Disney-movie-storyline-kind-of-way might consider taking me on as an intern. I’m up to around 22.

Then comes the polishing up of the old resume- I literally had one internship and an end date for a job to add to mine, and it took me two whole nights to do it. I had edited the insane settings and boarders and tables in the last iteration so much that anything I changed rendered the whole thing into an indiscernible mess, so I decided to start from zero.

I’m proud of it now… which brings us to the dreaded cover letter.

I hate everything about cover letters. They’re so ambiguous, and the stakes so high (for writing-related jobs anyway) that I don’t even know where to begin.

I mean, I know a bad cover letter. It’s easy. If you read it and hate the person because of it, you’ll probably hate them in real life too.

Come to think of it, reading anyone’s cover letter would make me dislike them at least a little bit… (Could you imagine Gandhi’s cover letter? How fucking smug would that sound? or even someone as professionally lovable as James Franco; how the hell would he describe his accomplishments and strengths and what he could add to a company without sounding like a dick?

But I digress. Before I can write one, I reasoned with myself, I need to read a lot about them… Which lead me right back to where I was a couple months ago trying to find anything that could help me in this petty yet critical chore.

The links were still purple.

But then I got stuck in my car. (Ignoring any speculation about what I was doing sitting in my car at 11 p.m. with just the barely audible radio on) a Scion TC pulled into the spot next to me and seconds later a man and a woman began to have a loud conversation directly outside the passenger side of my car.

I tried not to listen by reading search results several pages back, beginning with this, the cover letter Hunter S. Thompson sent the Vancouver Sun in 1958:


October 1, 1958 57 Perry Street New York City


I got a hell of a kick reading the piece Time magazine did this week on The Sun. In addition to wishing you the best of luck, I’d also like to offer my services.

Since I haven’t seen a copy of the “new” Sun yet, I’ll have to make this a tentative offer. I stepped into a dung-hole the last time I took a job with a paper I didn’t know anything about (see enclosed clippings) and I’m not quite ready to go charging up another blind alley.

By the time you get this letter, I’ll have gotten hold of some of the recent issues of The Sun. Unless it looks totally worthless, I’ll let my offer stand. And don’t think that my arrogance is unintentional: it’s just that I’d rather offend you now than after I started working for you.

The enclosed clippings should give you a rough idea of who I am. It’s a year old, however, and I’ve changed a bit since it was written. I’ve taken some writing courses from Columbia in my spare time, learned a hell of a lot about the newspaper business, and developed a healthy contempt for journalism as a profession.

As far as I’m concerned, it’s a damned shame that a field as potentially dynamic and vital as journalism should be overrun with dullards, bums, and hacks, hag-ridden with myopia, apathy, and complacence, and generally stuck in a bog of stagnant mediocrity. If this is what you’re trying to get The Sun away from, then I think I’d like to work for you.

Most of my experience has been in sports writing, but I can write everything from warmongering propaganda to learned book reviews.

I can work 25 hours a day if necessary, live on any reasonable salary, and don’t give a black damn for job security, office politics, or adverse public relations.

I would rather be on the dole than work for a paper I was ashamed of.

Sincerely, Hunter S. Thompson

(via Esquire)

Somehow the godfather of enjoyable political writing manged to capture — going on 60 years ago— my feelings (and the feelings of many of my recently-graduated friends):

Salutations faceless editor-boss,

I’m applying here so I can eat more than rice and beans but also do something productive for my career, and I’m sure it’s going to be a letdown working for you — either morally, editorially or technologically — but I’m doing my best to fake a smile about it.

Thank you for your time and consideration, early-twenty-something #8462

We were bred not for a “dying print industry” copy-and-pasted to the web, but to effortlessly fall into a foxhole on the battlefield of digital media domination and to do our part to contribute to the demise of the legacy press.

The conversation outside windows grew louder and dragged on. I found myself googling “plug slang” just to make sure this was a drug deal and not some kind of weird parking lot hook-up thing. Somehow they hadn’t noticed the light from my iphone or realized that the apartments just yards away could definitely hear their detailed strip club reviews. I found another link.

The New Republic’s early 2013 profile on Ezra Klein. I’m a big fan of Klein when it comes to presentation, style and the tools that Vox has come up with to tell stories. As a human though, he just seems like a shitty, rich liberal that cares too much about his image to really rock the boat.

The New Republic does not disappoint. It’s not… unnecessarily kind.

I didn’t realize that Vox was as new as it is- the piece takes place just a few months shy of 4 years ago but there’s no mention of it. He’s still improving WongBlog… God thing happen fast now.

Lets have a come-to-Jesus moment. We’ve all tweeted things — drunk and totally sober — that we REALLY regretted later and that (hopefully) nobody was paying enough attention to to call us out on. And it’s OK, because Ezra Klein, the guy who started one of the best news sites of all time, tweeted “fuck tim russert. fuck him with a spiky acid-tipped dick,” in 2008.

Other than that, the main takeaways are that 1) it probably sucks to be famous and insecure, 2) as long as you’re a super nerd when it comes to politics, you’re bad grades won’t doom you as a political writer (Klein graduated high school with a 2.2), and 3) it does kind of make sense to write about how you really feel about things (people, governments, geopolitical conflicts, etc.).

The 30-minute drug deal finally ended and I was able to go inside. Jazzed on the idea of leveraging my digital nativism to overtake the existing media environment (as opposed to assimilating into it — something I had stopped really thinking about a while ago), I decided to read up on Matt Yglesias, the other guy that started Vox.

Apparently he doesn’t let people profile him… which lead me to Matt Taibi’s takedown of a column he wrote last week, in which he literally argued that “Government officials’ email should be private, just like their phone calls.”

Taibbi’s piece is great, of course:

It’s kind of not our job in the media to worry about how officials might conduct politically embarrassing conversations without the press finding out. If that’s what Matt stays up at night worrying about, he might need a more news-appropriate hobby, like alcoholism.

I’ll drink to that.

I’m not really sure what any of this has to with cover letters, and I just lost a whole hour that I should’ve used to one that’s due ASAP writing this…

I guess the point is this: if you can’t be a Thompson, be a Taibbi. And don’t ever settle for being an Yglesias because you can at least be a Klein.

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