5 Dilemmas You Face When Writing A Cover Letter


1. The Greeting Dilemma

Do you…

A. Begin with a “To Whom It May Concern”?

B. Just face the facts and go with a “Dear Unpaid Intern, whose (and I mean this very loosely) ‘job’ it is to preview resumes and cover letters for the hiring manager who’s too busy ordering 8 oz. of $985 caviar from the Dean and Deluca website”?

2. The Opening Sentence Dilemma

Do you…

A.  Introduce yourself first with a simple “My name is John Johnson”?

B. Attempt to use the first sentence to make a lasting first impression via threat with “My name is John Johnson and I have your cat. He’s in a box with a small flask of hydrocyanic acid, a Geiger counter, and a radioactive isotope with an incredibly short half-life. If I do not receive an e-mail reply with a job offer within 24-hours, there is a 100% chance I will take the cat out of the box and shoot it. Oh yeah, and there is also a gun next to the box”?

3. The “Why You Should Hire Me” Dilemma

Do you…

A. Try to make the argument that you, who attended a state “party school” in the south, an entire region whose educational institutions aren’t taken seriously by employers in New York anyway, and finished up with a B.S., as in “bull” and “shit,” degree in English, ought to be hired for this Marketing Assistant position?

B. Just admit that the job should go to the other applicant who graduated from Princeton in two years with a degree in Business, fluently reads, writes and speaks English, Mandarin, and Zulu and spent the last two years of high school studying abroad in the Junior Peace Corps building houses for impoverished villagers in Mali?

4. The Work History Summary Dilemma

Do you…

A. Attempt to weave a flimsy narrative thread between your grocery-store bagging job, your strip-mall, retail job at GameStop, your post-collegial stint as a public school teacher, and your recent months of occasional office temping and unemployment void before explaining (hopelessly) how the skills you acquired in these quasi-professional experiences marginally relate to marketing assistantdom?

B. Admit that your employment history is a nebulous clusterfuck of go-nowhere jobs that you only took to avoid manual-labor, living out of your car, sleeping on a couch, and/ or having to move back home?

5. The “Sincerely,” Dilemma

Do you…

A. Close the letter with a “Sincerely,” when you know full well that sincerity didn’t even make it past your greeting, much less the rest of your sub-literary and, frankly, corporate whorish cover letter?

B. Close the letter with a “Fuck you,” after realizing it won’t matter anyway because your letter will be skimmed at-best, your resume will go unread, and your e-mail will be deleted before ever reaching the inbox and eyes of the hiring manager that probably wasn’t going to reply because s/he has their Gmail automatically mark all e-mails containing the word “resume” as spam?

C. Save the cover letter as draft, sigh, eat another bowl of Cocoa Pebbles, stream another episode of The Office on Netflix from your 3-year old MacBook, Command-H your Google Chrome, check for new messages on Mail, have none, close your MacBook, take a 4- to 5-hour day-nap, and dream about an alternate reality in which you graduated into a 1990s economy instead?

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