A Freelance Writer's Life: The Art of the Pitch

I called myself a freelance journalist long before I had any idea how to be one. I was 24. I even had business cards printed: Alex Crevar, Freelance Journalist. They might just as easily have read: Alex Crevar, Haberdasher, or Alex Crevar, Taxidermist.

What I didn’t know then was that the key first step to becoming a successful freelance writer (perhaps the most oxymoronic phrase in any language) is crafting a watertight, clear and brief story proposal—in journalism parlance, a pitch. Everything else rises from this foundation. From a pitch, an assigning editor will know: how long the writer has been working as a freelancer, how much information she has about the subject presently, whether she has the wherewithal to learn more, and how reliable she will be to bring the story home.

Surely a sage such as myself, who has worked as a freelancer for nearly two decades, must have received some from-on-high knowledge about creating pitches, right? Uh-uh. My early pitches were such shite that I routinely received hard-copy letter responses from editors (yes, before email was the medium of the day) with nearly indiscernible words hand-scrawled diagonally across the length of my typed, stamped and mailed proposals. “Unreadable,” one editor wrote, leaving off the last “e” because he couldn’t be bothered to even finish writing the word. Another said: “Not a story.” My favorite (now—not then): “What the f*&k is this?”

My early pitches were such shite that I routinely received hard-copy letter responses from editors with nearly indiscernible words hand-scrawled diagonally across the proposals.

Like many hopeful writers, I envisioned a life on the road documenting what I saw. In my mind, editors would beg for the chance to read my unique experiences. They’d read inspiring stories of me riding trains and roughing it across Europe. They’d tell their wives and husbands to keep dinners warm because they couldn’t leave their desks until they finally discovered just how beautiful the beach was where I was lounging. They’d stop the presses to make room for my groundbreaking stories of grizzled old locals wearing lederhosen and speaking to me, steins in hand, from alpine valleys.

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Maybe the stories would have an angle, ehhh … but that hardly seemed pertinent to me at the time. Largely my yarns would be real slice-of-life stuff, you know? Editors would just eat it up. I mean really, how could they resist the nuanced and intricately textured musings of a sheltered, middle-class white kid?

Such egocentric idealism is healthy in the beginning and for about a minute. Such idealism will carry a young writer for the briefest of whiles. But, in order to actually become a regularly published writer, this idealism, I learned, has to quickly jump in the backseat and let professionalism drive.

Oh, that word. Professionalism. How easy it is to type. How hard it is to actually learn. For freelance writers, professionalism is not one thing. Becoming a pro means being aware of all the little things that tie into the overall package presented to an editor. That package begins with the spark of an idea and ends only when the story has gone to press.

Trey Ratcliff.jpg
Photo: Flickr/Trey Ratcliff

Cracking the code and understanding the many shifting algorithmic combinations needed to succeed does not come easily. It comes in stages. It comes after knowing, just knowing, that writing for one big national glossy is all it will take to break through. It comes after countless responses from editors that essentially read: “Good try, but we’ll pass.”

And though there are a lot of little things that a freelancer must do to earn and then keep an editor as a client—a solid pitch, clean copy, solid fact-checking and early communication when stories have issues—there is one sentence that encapsulates the entirety of a writer’s mission: “A writer must make an editor’s job easier.” Why is this line in quotes? Because this single line was emailed to me, by itself, years ago after I had habitually broken this cardinal rule.

A writer must make an editor’s job easier. Full stop.

What does that mean? It means a freelancer must treat his job like he’s a salesman, not a bon vivant (unless he can do both). A salesman who hopes to earn a client knows who his client is; he knows what his client is looking for; and knows he must make the best pitch possible to sell his widget (likening a story to the classic, hypothetical products of Marketing 101 classes) to a client who is listening to scores of widget pitches per day. The simple question: why would an editor want to buy my widget over a similar widget being sold by Jane Doe? Because I started with a solid pitch—one that makes plain this is not my first rodeo … even, perhaps especially, if it is.

Photo: Flickr/IamNotUnique

My first pitches were rambling, smoke-and-mirrors affairs. They resembled most of the school papers I’d ever written. There was the little voice that said, “If you write long enough and use enough big words the teacher will certainly give you a good grade if for no other reason but because you’re among the brightest kids in the class.” What I soon learned: when you write for a living, everyone was the brightest kid in his or her class. Editors don’t give out grades if the pitch is subpar. They hit delete.

What I soon learned: when you write for a living, everyone was the brightest kid in his or her class.

I had one saving grace in those days: I was more than a little nuts. Instead of pitching a story about a city near me, I’d travel to a place I thought no one would get assigned (and one that might be interesting), learn about it and then send in the idea. Really the only benefit moving to post-war Sarajevo, Bosnia, bought me, though, was a guarantee that an editor would read the pitch. Even given the fact that no editor would have sent her travel writers to a conflict-worn city, I still received responses saying (at that point via email), and I quote: “You need to be more clever.”

Then I received an email that changed my thinking for good. I am certain the editor wasn’t trying to be helpful, but he gave me more in one email than nearly every story I’ve ever been assigned: “Please stop pitching me stories. You are sending ideas that have no time peg, no news peg, and are not interesting except to you. In this business, silence means no.”

At that moment, I had two choices: create a system and sell widgets clients wanted, or do what most smart, former freelance writers do, leave this horribly paid existence, marry up and become sane. I opted for the former BUT tried to make a science out of it. The science became the four-paragraph (in journalism speak: four-graf) pitch.

Photo: Flickr/Kerri Lee Smith

The format and the grafs had to overwrite all of my bad habits and get to the point of the idea in a timely fashion. The entirety of what I have learned about pitching, in two decades, I am laying out here in the course of about 15 minutes.

Salutation
Always begin with “Dear” and then the editor’s name, position and magazine. Never again would I act like a punk and say “Hi Jennifer, do I ever have a great pitch for you!” All business. Nothing cutesy.

First Graf
This has to kick an editor square in the teeth. The clear lead sentence, and then supporting graf, should hook her and make her know that 1) this piece is timely; 2) her readers will need to read about this place; 3) you are an expert (whether you are or not).

So, my dreams of pitches like: “You should really let me write a story about XYZ beach! Everybody loves it!” were thrown straight out the window.

Second Graf
What will actually be in the story? In this graf, I’d give the editor a skeleton, at least, of activities for the locale. I’d provide historical context. I’d back up the idea’s timeliness and why I believed it had specific relevance to her publication. (An editor, by the way, then has to “sell” an idea to a roomful of editors at an upcoming editorial meeting. If my idea was a complete dog, I could be damned sure the editor wasn’t going to fall on a sword for me.)

Again, no more of this: “Hey, I know your mag specializes in boating, but I really think your readers would get oodles out of learning about skiing in Italy!”

Third Graf
This graf ALWAYS begins with this exact phrase: “I propose a story about—” Besides the lead sentence, this is the single most important line of the letter. I was determined to be very clear about what widget I was trying to sell. The editor may not want the story. She may have already assigned a similar story to another writer. She may just not like the name Alex, but she would know exactly what I was pitching.

Fourth Graf
This paragraph explains why I am the right person to write the story. It shows why I know more than the average person about the place; what sources I am planning to contact for the piece; who I have already contacted; what publications I have written for before; and that I have attached clips (previously published pieces) to the email.

Closing
“I look forward to your response, Alex Crevar.”

Why would I leave a person I don’t know with Cheers? Frankly, if they say no to the pitch—which is still the norm—I don’t want to waste a “cheers” on them. And if they say yes, it isn’t because they thought I was clanging beer glasses with them. It will be because I provided a clear, attractive pitch to sell my widget.

Do I sell all of my story ideas? Not even close. Do I get respectful responses that sometimes lead to future stories? The results after the implementation of my four-graf-pitch scheme are exponentially higher. Do I hope any of this helps even one aspiring freelancer, who is like me but smarter? Absolutely. I can’t wait to read your stuff and plan my next vacation.

Alex Crevar is Paste’s travel editor.

A Freelance Writer’s Life: The Art of the Pitch