The Art of the Cover Letter

As someone who loves to write, it’s depressing when I don’t actually enjoy writing something. I mean, I even enjoyed writing (most of) my papers in college. But there’s one writing task that hurts the very fiber of my soul, and that is writing a cover letter.

If I could write three paragraphs of pithy self-deprecation, I promise you I’d have gotten a job within a month of moving to Chicago. But nooo, I’m supposed to write a few concise paragraphs about why I’m great. Are you serious? Obviously I don’t feel too great—I’m writing a cover letter and essentially begging you to hire me. I am a hooker. [*Disclaimer* I am not a hooker. But this is how you make me feel, COVER LETTER! Damn you!]

The cover letter is the first of many painstaking steps to getting a potential job. Next, you check your email 65 times a day, or maybe an hour, hoping this potential employer has responded. You jump every time your phone rings, thinking that might finally be the call asking for an interview, only to discover it’s a message from Sprint telling you your payment’s overdue. Or…maybe that’s just me. But, in brief moments of blissful hope and possible employment, you land an interview! Then you get to sell yourself in person.

Oh, the interview.

What’s even better is when you have the interview that goes so well, you leave just knowing, deep in your gut, that tough times are over. In my case, that happened in November, when I interviewed for a job at Northwestern. Clearly my gut, as John Cusack would say, has shit for brains. I drove back to my apartment that day, smiling, daydreaming about buying the fam Northwestern shirts as Christmas gifts. Hmmph. Yeah, I’m not working for Northwestern. In fact, even though they assured me that, no matter what, I would hear from them about the position, let’s just say this: Not only am I not working for Northwestern, I’m still waiting on my rejection.

In this past year, I have gone on no more than five interviews. FIVE! Have you any idea how that compares to the number of cover letters I’ve written? Any idea?

Well, my math isn’t that great, but I’m pretty sure I’m doing something wrong.

So, tonight, as I was pondering how to master the art of the cover letter, once and for all, I had a breakthrough. What would Costanza do?



“I had so much promise. I was personable, I was bright, oh, maybe not academically speaking, but I was perceptive. I always know when someone’s uncomfortable at a party.”

I know exactly what you mean, George Costanza. And that’s why I wrote a cover letter tonight, and instead of ending with my tried and true line, “Thank you for your time, and I will follow up with you in the next week to see if I can provide you with any more information,” I wrote this:

“I'm sick of serving beers. I'm ready to use my talent. Please give me a call.”

This was the follow-up to my opening zinger, “I am a motivated, talented writer/editor, and my skills are being wasted while I serve beers and burgers at a Logan Square bar and grill.”

What do you think? Cover letter suicide? Or did I make Costanza proud?