There is probably no writing task so loathsome as the cover letter. This creaky institution is an exercise in stoic awkwardness, leaving you to blindly guess and stab at how to charm a mysterious reader. If you’ve ever been on the receiving end of such missives, you know with almost certainty that any attention paid will be swift, and judgment snap.
There is so much to be said for the ability to interpret the signs of someone’s physical presence. In person, our minds subconsciously calculate the cues that help decipher how a person wishes to be addressed. The missing value in this is felt acutely when you are staring down a blinking cursor, trying to write yourself into a favorable fate.

What’s more, attitudes toward the very necessity and relevance of the cover letter vary wildly. Some say it’s old fashioned, corny, and therefore your very participation in the process of such a thing marks you just as moldy and out of touch—hardly the material for these future-thinking times! Or, perhaps your mysterious reader (Will it be the HR specialist or a Creative Director? A potential rival? No one at all?) is of the philosophy that a good business strategy entails being careful not to miss the opportunity for a touch point. And so should we not, as the business managers of our own lives, take advantage of the opportunity to connect with a potential consumer of our talent?

Ironically, as a writer this is doubly hard, putting you on the spot as the embodiment of all things: respectful of protocol yet bold and trendsetting, humble yet game changing, etc. You are trying to make the case that this is what you’re good at, is it not? It’s awful. The pressure may not be as steep for other types of candidates, and yet it seems to be even more important for those whose profiles are visually heavy—designers, art directors, etc. Communication is so fundamental to the tolerability of any creative collaboration that it’s understandable to want to get a taste of someone’s personality… and yet I can’t think of a better set of pressures to thrust upon someone as a preventative to relaxing and being one’s self.
It’s emboldening to know that some staffing agencies—including Creative Circle—have consciously made the decision to do away with the practice. As an impartial, but constant, observer of hiring practices, and an advocate for both sides of the equation, their assessment seems trustworthy.

Progressive ideas being what they are, however, these opinions are far from having transformed the hiring landscape as a whole. More often than not, a cover letter is requested. Even a hip company will want one, they just might not say it directly. (Look for faux-casual euphemisms like “Convince us, go!” or “Here’s where you do you!”) As much as I hate them, I can’t deny the potential of a cover letter as a creative challenge. If only the ROI wasn’t so erratic!

In general (and particularly as regards anything that pertains to fashion, including manners as much as dress), I think it’s solid advice to err on the side of formality. A dexterousness with the rules proves your capability of breaking them, and all that. I think the thing to do is to screw up the courage to face the dread cover letter as what it is: a gnarly assignment to test your sense of universal tact, your ideas about neutral, receptive friendliness, and your self-perception. (No big deal.)

And yes, the maddening reality is that whether you dash it off without much concern or turn your mind inside out over it, there is a better-than-half-chance that your effort to impart a universally appealing whiff of your very self will never even reach its recipient. Ours is a professional culture born from multitudes of interpersonal chemical reactions combined with the completely blind luck of time and place. Whether or not you embrace the cover letter—or maybe even, as I suspect some of us secretly hope, revolutionize it (!)—you’ll most likely find your place in an environment that shares your attitude. It’s just another piece of the personality puzzle that determines our course.

So yes, they’re right. This is the part where you do you.


Marjorie is a Creative Circle candidate based in Portland with a longing for work-related travel. She is a writer/editor and stylist/producer with an emphasis in the design world. If you are interested in working with Marjorie, please contact Creative Circle Portland.