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How Not To Write A Cover Letter

Illustration for article titled How Not To Write A Cover Letter

We're getting close to graduation time, which means that it's time for America's college students and freeloading grad students to undertake the ultimately fruitless quest of begging corporate America for gainful employment. If you've ever searched for a job, you know what a mortifying experience this can be, and Funbag reader Max took issue with one particular aspect of it:

I am a law student. As a 2L, one of the biggest burdens is finding that very important summer job between your second and final year of law school.

Our career development office is minimally helpful, which leads me to think they only work about 90 minutes a day. There is no greater dissuasion for me applying for a job when the words "Please include cover letter" appear on an application, as well as my general apprehension due to my shitty GPA. My question for you is how does one write a cover letter that does not come across as completely insincere and boilerplate-ish? Phrases like "I am an independent self-starter..." or the like cause me complete anguish that I refuse to write them altogether.


I've never understood why some employers demand a cover letter sent in with a resume. It's a dick move in so many ways. It's giving you extra homework that you shouldn't have to do. And it's basically saying to people, "Can you please waste both paper and time in the clumsiest way possible?" No HR department lackey is gonna spend time reading a cover letter. All they wanna know is if you went to a decent school and if you aren't a registered sex offender. If you make it past that round of cuts (and you probably won't, because American employers expect way too much of people), then they have to bring you in and meet you face-to-face to make sure you aren't an asshole.

There are only two things to do when writing a cover letter. The first option is to make it as straightforward and to-the-point as possible:

Dear sirs (NOTE: I always used to write "sirs" in my cover letters because I never knew who to actually send my resume to, which meant that my resume probably went into the mailroom trash before even being opened),

My name is (YOUR NAME!). I'm a second year student at (YOUR SCHOOL!), and I'm writing to express interest in the position of (JOB!). I have a great deal of experience in (SHIT THAT JOB REQUIRES), since I (REPEAT ALL THE SHIT IN YOUR RESUME).

I will be in (YOUR TOWN!) the week of (DATE YOU CHOSE AT RANDOM), and I may be free then to meet with you to discuss this position further. Please call me at (YOUR NUMBER!) or email me at (YOUR EMAIL!) if you have any questions. I look forward to meeting you.



That's a standard cover letter, right? It's basically your resume, just rejiggered into letter form. Plus, you mention that you MIGHT be able to meet with them because you're a crazy busy awesome guy and you've got offers from Patton Boggs and 60 other firms to consider. It's boring, but at least it's professional. No one will discount you because of that cover letter.


That's the first option. Now the second option—and this is always where cover letters go hilariously wrong—is to get cute and try to make an IMPRESSION with your cover letter by doing something all wacky and zany and all meta about the cover letter process. Like so:

'Sup Guys?

Let's get right to it: You've got a job opening, and I needs me a jobbie job. I'm not gonna try and dazzle you with some batch of cover letter bullshit. Yeah, I swear sometimes. Who doesn't? All you need to know is that I was the head of the CSU-Fullerton Law Review and in my three years there I fucking CRUSHED it. Just fucking SLAYED that review. I worked hard, and then I played hard, and I know that's what you like to see in a (name of firm) man. Here are my deets. Y'all know where to reach me. PEACE TO THE OUT.


Now, this is the kind of cover letter that, even in a free country, should land you in prison. And the amazing thing is how downright tempting it is to write something like this when you're young and searching for a job for the first time. I remember sending out cover letters my senior year and thinking to myself: "Pfft. I'm not gonna write some BORING cover letter. I'm gonna fucking melt their faces off with a cover letter they've never seen before!" I used to type up irreverent cover letters and then daydream about the CEO reading it (before I got my first job, I assumed the CEO was in charge of hiring all people) and being so dazzled by my originality that he hires me for a senior position sight unseen. Then I showed one of these letters to my dad and he nearly threw me out the window.

There's no good way to write a cover letter because your two options are to be boring or to terrify everyone by trying to NOT be boring. Anyone who can write a truly wonderful cover letter—a cover letter that both addresses a younger brother's fight against leukemia and lays bare an unparalleled passion for patent and IP litigation—probably already has a job and a Nobel Prize anyway. All you can do is send in that resume and pray that the HR person sifting through all the shit on her desk at lunch pauses on your profile between bites of a Panera salad and thinks, feh, good enough.


When I was in college, I sent out cover letters to all these big companies and ad firms, even if they had no job available. I even bought fancy paper stock, since this was right before email became omnipresent and I thought fancy paper made me look classy. And the fun thing about doing sending out letters like that is that you can then go tell people that you've got irons in the fire. "Oh yeah, I'm in the running for jobs at Apple, Nike, and Coca Cola. We'll see what happens!" You're able to give yourself the illusion that one (or more) of these things will pan out, even though that's nowhere close to being true. I bet most of these companies just take your info and put it into their customer database so they can sell it off to direct marketers (Note: This happens with every job listed on Monster). I have no clue how I ended up getting my very first real job. I can't remember what it was that I did right (although I know exactly why I was laid off two years later), and I'm not sure there is a right way of going about it. Either you have to be a genius or you have to know someone, and no cover letter is ever gonna make a difference. Cover letters are stupid.

Fish hook photo by Joe Belanger/Shutterstock.