An Open Letter To Young Writers Applying For Writing Jobs

As far as I’m concerned, it’s a damned shame that young writers’ cover letters sound sterile and devoid of any emotion, hag-ridden with mediocrity, boredom, and apathy. If this is what you’re trying to show your potential employer, then I think you’re not going to work for anyone.

With apologies to Hunter S. Thompson (more on that in a minute), if you’re a young writer looking for writing jobs, you can’t write a regular cover letter to get an employer interested in you. (Ditto for experienced writers. You just ought to know better by now.).

You can’t follow the same formula your career services advisor gave you, or the advice you’ve read in other career articles. (See LifeHacker’s article on how not to write a bad cover letter.)

Hunter S. Thompson, Miami Bookfair International, 1988Your cover letter has to kick ass. It has to be moving. It has to be so amazing that the hiring manager leaps out of her chair, clutching your letter in her hand, shouting, “Eureka! I’ve found him!”

Think about it: the one thing you’re good at, the one thing you’ve trained for and worked toward over the last several years, and you already show you suck at it with your cover letter. How much confidence is that going to instill in anyone? As a writer, it’s your responsibility — nay, your duty — to knock this thing out of the park.

You can’t open with, “To Whom It May Concern: I am interested in applying for the junior copywriting position I saw on your website.” Of course you are. Why else would you write a letter with your résumé and press clippings?

Do what you learned in journalism or creative writing and make your opening lead as dramatic and attention grabbing as you can.

Try, as Hemingway once said, writing drunk, and editing sober. Be bold, be daring, be a little crazy. Inkslingers are not known for being completely stable, especially when showing off for other writers. And you’re sending your best work to other writers who will silently, but instantly, judge you for the quality of your cover letter. So show off.

A letter that a young Hunter S. Thompson wrote to the publisher of the Vancouver Sun asking for a job is still making the Internet rounds with people reveling in its audacity, wondering if they could pull something like that off.

Of course, at age 21 Thompson was, as the Gawker called, an arrogant little shit. But maybe there’s something to it.

You may not want to go insulting your potential new employer by calling his people dullards, bums, and hacks, at least not if you want to make friends there. But there’s something to be said for letting your voice shine through.


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.

I didn’t make myself clear to the last man I worked for until after I took the job. It was as if the Marquis de Sade had suddenly found himself working for Billy Graham. The man despised me, of course, and I had nothing but contempt for him and everything he stood for. If you asked him, he’d tell you that I’m “not very likable, (that I) hate people, (that I) just want to be left alone, and (that I) feel too superior to mingle with the average person.” (That’s a direct quote from a memo he sent to the publisher.)

Nothing beats having good references.

Of course if you asked some of the other people I’ve worked for, you’d get a different set of answers.

If you’re interested enough to answer this letter, I’ll be glad to furnish you with a list of references — including the lad I work for now.

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.

It’s a long way from here to British Columbia, but I think I’d enjoy the trip.

If you think you can use me, drop me a line.

If not, good luck anyway.

Sincerely, Hunter S. Thompson

Not surprisingly, Thompson didn’t get the job, but don’t let that stop you. You don’t have to be as over the top as Thompson was 45 years ago (and especially don’t be as over the top as he was 10 years ago), but try to incorporate some of his boldness in your next cover letter.

After all, the stuff you’ve been sending hasn’t been doing you any good, so what do you have to lose?

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    About Erik Deckers

    Erik Deckers is the President of Pro Blog Service, a content marketing and social media marketing agency He co-authored four social media books, including No Bullshit Social Media with Jason Falls (2011, Que Biz-Tech), and Branding Yourself with Kyle Lacy (3rd ed., 2017, Que Biz-Tech), and The Owned Media Doctrine (2013, Archway Publishing). Erik has written a weekly newspaper humor column for 10 papers around Indiana since 1995. He was also the Spring 2016 writer-in-residence at the Jack Kerouac House in Orlando, FL.


    1. I am interested in leaving a reply to your blog post. I will start with “Nice post!” before moving onto several banal comments of the industry at large and a few compliments of your writing, which I mainly skimmed.

      I will then end with a link to my site,

      Erik – flattered you’d write a post off a brief Twitter convo we had. I think the core of these awful cover letters might be this: somewhere in our education, we were incorrectly trained that the purpose of writing a cover letter is to really nail writing a cover letter. And we learned the template for doing so. We also learned that a business is a faceless, humanless entity which expects and accepts a certain way of doing things (like reading covers).

      Seriously — my first few jobs, I did the same thing. It wasn’t because I couldn’t write a better cover letter (I’m ok at the thing where you put the words into the larger things that people scan with their eyes and stuff); I was genuinely AFRAID to not construct the right letter, misguided section after misguided section, as seen in my college career center’s samples. I was convinced that I’d be FROWNED UPON if I tried to be creative, as if taking that risk would paint a negative picture.

      As always, I think this starts with education. Hopefully, this stops being the case soon.

      • Jay,

        I think this was definitely a post that needed to be written. I think this is but a symptom of a bigger problem Seth Godin has identified and spoken of in Linchpin (I think) — we’re all taught to be good cogs in a larger machine, which means following all the right formulas, so we can show we’re a good cog.

        I did exactly the same thing, even as recently as a few years ago, but I’ve decided to be bolder in my approach to most things, and have promised myself if I ever have to look for a job again, I’m going to try being audacious.