Selling yourself often feels like a grotesque act. So job applicants’ cover letters seem unlikely to contain much great prose. Instead, we tend to fill the page with false notes and empty phrases. (“I believe my skills make me the ideal candidate, and I would appreciate your consideration…”)
But it doesn’t have to be that way. When a 30-something Leonardo da Vinci sought work in the court of the duke of Milan in the 1480s, he wrote a short, bulleted list of ten skills that would have been sure to catch the eye of any Renaissance-era ruler: he could design portable, indestructible bridges; build unassailable vehicles; destroy most fortresses; and so on. (He also could “execute sculpture in marble, bronze and clay,” and wasn’t so bad with a paintbrush, either.) His letter was brisk, convincing, and a pleasure to read.
Other fine examples of the form can be found in the cover letters of Eudora Welty and Hunter S. Thompson, among other great minds. Quartz distilled their wisdom into a rough guide to cover-letting writing.
It’s worth noting that these letters aren’t templates—it would be pointless to copy correspondence that’s so individual. They’re here as prods, reminders that it’s possible to make a necessity of business a bit less of a drag to write and read.
All but one of the letters mentioned here come from the recently published book Letters of Note: An Eclectic Correspondence Deserving of a Wider Audience, an anthology of Shaun Usher’s wonderful blog of the same name. It’s well worth picking up.
Cut Through the Noise
The trouble with most cover letters is that they sound canned. Using boilerplate formalities won’t make you sound serious; it will just make it harder to tell one cover letter from another. Use your personality, even if it means channeling your anxieties about the job you hope to get. For instance, Eudora Welty opened with a bit of disarming humor when she applied for a job at The New Yorker in 1933 as an unknown 23-year-old writer with no experience:
I suppose you’d be more interested in even a sleight-o’-hand trick than you’d be in an application for a position with your magazine, but as usual you can’t have the thing you want most.
And she closes with a self-deprecating joke and an amazing pun:
There is no telling where I may apply, if you turn me down; I realize this will not phase you, but consider my other alternative: the U of N.C. offers for $12.00 to let me dance in Vachel Lindsay’s Congo. I congo on.
Both you and the person reading your application know that you’re engaged in a dull little ritual. Anything to break up that monotony is likely to get you noticed.
Be Specific About Your Skills
Da Vinci’s letter to the ruler of Milan, Ludovico Sforza, overwhelms the reader’s defenses with details of his war-waging abilities, from constructing secret subterranean passageways to designing “very beautiful” cannons and catapults:
1. I have plans for very light, strong and easily portable bridges with which to pursue and, on some occasions, flee the enemy, and others, sturdy and indestructible either by fire or in battle, easy and convenient to lift and place in position. Also means of burning and destroying those of the enemy.
4. I have also types of cannon, most convenient and easily portable, with which to hurl small stones almost like a hail-storm; and the smoke from the cannon will instil a great fear in the enemy on account of the grave damage and confusion.
Welty’s talents were less martial but equally impressive:
I recently coined a general word for Matisse’s pictures after seeing his latest at the Marie Harriman: concubineapple. That shows you how my mind works—quick, and away from the point.
Try to Show Your Skills in Action
It’s one thing to say you can do the job; quite another to show it. In 1934, Robert Pirosh was a young copywriter who wanted to break into Hollywood. The brief cover letter he sent to directors vouches for his abilities better than a lengthy CV could:
I like words. I like fat buttery words, such as ooze, turpitude, glutinous, toady. I like solemn, angular, creaky words, such as straitlaced, cantankerous, pecunious, valedictory. I like spurious, black-is-white words, such as mortician, liquidate, tonsorial, demi-monde.
And so on for another 100 or so peregrinating, bravura, gurgling words. Pirosh was hired as a junior writer for MGM, where he wrote for the Marx brothers and won an Academy award for Battleground.
Tell a Story
Making our lives and experiences intelligible to others is a hard task. But if you can sustain a narrative over the course of a few paragraphs, you’ll seem like a person, instead of a faceless email. When Tim Schafer applied to be a programmer and designer at Lucasfilm in 1989, his cover letter came in the form of a text adventure game.
Your quest for the ideal career begins, logically enough, at the Ideal Career Center. Upon entering, you see a helpful looking woman sitting behind a desk. She smiles and says, “May I help you?”
>SAY YES I NEED A JOB
Things ended well for the game’s character (“As you become personally fulfilled, your score reaches 100, and this quest comes to an end”) and for Schafer too, who went on to design a string of popular video games for Lucasfilm and his own company, Double Fine Productions.
Make Your Interest Palpable
Why couch your enthusiasm in stilted, formal phrasing? You want this job. So say it, like Welty does: “How I would like to work for you!”
Be Clear About What You Want, and Don’t Want
In his 1958 cover letter to the Vancouver Sun, a 21-year-old Hunter S. Thompson wasn’t shy about broadcasting his abilities—”I can write everything from warmongering propaganda to learned book reviews,” he wrote. But he also detailed battles with his previous boss (“It was as if the Marquis de Sade had suddenly found himself working for Billy Graham”). He explained his reasoning:
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…. 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.
Thompson’s cover letter might not seem like one to emulate. (He didn’t get the job.) But his blunt tone served a good purpose: It likely saved him from a workplace he would have hated, and helped lead him to jobs that were more suitable to his interests and talents. As he wrote, “I would rather be on the dole than work for a paper I was ashamed of.”
A Letter Is a Great First Step, but Try to Set Up a Face-to-Face Meeting
After da Vinci listed everything he could do to elegantly crush an enemy, he offered to show his skills in person, just in case his descriptions weren’t convincing:
And if any of the above-mentioned things seem impossible or impracticable to anyone, I am most readily disposed to demonstrate them in your park or in whatsoever place shall please Your Excellency, to whom I commend myself with all possible humility.
Stay Alert to Other Opportunities, and Be Patient
Da Vinci asked to join Sforza’s court as a sort of battlefield engineer, but the Milanese duke ended up becoming one of his most important artistic patrons, commissioning “The Last Supper” along with important works of science and architecture.
And Welty wasn’t hired by The New Yorker initially, but she did eventually end up writing for the magazine over the course of her storied career. It just took a couple of decades of waiting.
If It’s Your Dream Job, Don’t Worry About Your Qualifications—Just Apply
Sam Pointon didn’t quite have the requisite education and work experience when, in 2009, he applied to be the director of the UK’s National Railway Museum. But you wouldn’t expect him to—he was still in elementary school. His letter began:
I am writing to apply to be the new Director of the National Railway Museum. I am only 6 but I think I can do this job.
I have an electrick train track. I am good on my train track. I can control 2 trains at once.
Like Thompson and Welty, he didn’t get the job he applied for. (At least not yet.) But the museum was impressed with Sam’s enthusiasm, and—perhaps sensing a PR coup—it created a new position for him: Director of Fun. A museum spokeswoman tells Quartz that Sam “retired at the grand old age of 10 in summer 2012 so he could focus on his studies.” Not a bad run for a first job.