The Art and Craft of Freelancing (Part II)

EDITOR’S NOTE: This is the second of a multi-part series on freelance journalism. The idea for these posts came from an instructor who was adopting the News Reporting and Writing and said she would love to see a section or discussion on freelancing in there somewhere. When my editor mentioned this to me, I promised I’d work on it for the blog.

Today, we get into the pitch itself and how to get it accepted. Part I is here, along with a good introduction to three freelancers who were nice enough to help me understand their business: Charles Choi, Tony Rehagen and Nick White.

Do you have a “I wish your book had included X” element? Contact me and I’ll see what I can do to make it happen.

Building your pitch

The key to a good story is also the key to a good pitch. Consider the following questions when you look at your pitch:

  • Is it clear, concise and have value?
  • Does it get to the point or does it get lost in the details?
  • Does it make the reader want to read on?

You should grab the reader’s attention, show them enough to make them want more and then offer them the opportunity to get it. Here are a few thoughts about how best to build that pitch:


Know your audience: One of the biggest points each of the freelancers made was that knowing the audience of the publication and knowing the audience that was reading the pitch letter (the editor) was crucial to success.

“If you are pitching a new outlet, first you should have an introductory paragraph describing who you are and whom you have written for, and an end paragraph providing links to some stories,” Charles Choi said.

Choi said that once he got to know his editors at various publications better, he knew how to tailor his pitch to each one.

“For the outlets I usually write for, novelty is by far the most important factor in what I pitch — no point writing up something if it isn’t news,” he said. “Just as important is how interesting the audience of an outlet would find a pitch — for instance, the audience of Wired might like stories about microchips that can simulate brain cells, but not be as interested as the audience of IEEE Spectrum (a more technical publication) would be in other advances in microchips… All in all, it is crucial to know what the audience of a given outlet likes, and that is something you can best find out by reading a dozen or two recent stories from that outlet.”

Some editors just needed to know he had an idea while others still needed a full pitch that hit on the key elements we’ll discuss below. Choi said it’s also important to understand how to use the right tone and feel when it comes to telling the editors about the story.

“If you are writing a short article, your pitch should have a lede sentence that will often also serve as your nut sentence,” he said. “This single lede/nut sentence should sum up what is new and interesting in a snazzy, provocative way that will make you want to read the rest of the story. You may want to follow this lede with at least one or two sentences describing the potential broader implications of this lede sentence.

“If you are writing a longer article, you may start off with a lede that brings up an interesting anecdote, or introduces an interesting person. After one or two paragraphs of this, then you have a snazzy nut sentence or paragraph that sums up the story and makes you want to read the rest of the story. You may want to follow this lede with at one or two or more paragraphs describing the potential broader implications of this lede sentence.”


Get to the point: Editors are busy people and have a dozen or more things to do that are more important than you might be at a given moment. Therefore, you don’t want to waste their time. Tony Rehagen said the body of a pitch should do three key things:

“It’s like writing a short story,” he said. “You have to 1. Grab the editor’s interest 2. Explain why the story is right for the pub and the time and 3. Show that you’re the writer to do it.”

Nick White’s standard approach mirrors this idea:

“A pitch model shown in grad school at Medill that I follow in my head was brief, with a rapport attempt at top, a quick pitch with embedded knowledge in the middle for one or two short paragraphs, and an invitation to drop a line if interest at the bottom,” he said.

In both cases, the idea is to share knowledge, not hype. Nail down your crucial elements quickly and make your case for story in a few short paragraphs that tell the editor you know what you’re doing and that you can be trusted.

Edit the heck out of it: Once you complete your pitch, you need to make sure this thing is cleaner than a cat’s mouth. Is it clear? Did I get too far afield? Was I redundant? If you’ve got redundancy problems, chances are editors will not want to bother with this story as it’s clear they will need to invest a lot of time in fixing your story when it shows up. The same is true for grammar and style. If the editors can’t trust you to spell stuff right, how can they trust you to get the big things right?

“If I’m pitching a new outlet or an outlet I write for only rarely, I not only give a lot more details regarding the story is about, but I craft the writing of the pitch to let them know that I can write well and to give them an idea of what to expect if I were to write that story for them,” Choi said.

In the minds of most editors, the quality of the writing in the pitch will reflect the quality of the writing in the story. Nobody wants to borrow trouble, so make sure you are clean and clear in your writing and editing.


A simple breakdown of a pitch letter:


If you’re doing the “old-fashioned pitch letter,” the standard topper information is a good idea to include. Even though most of what you’ll do is via email, we’re including this below so that you can get a sense of the audience for the pitch:

Bill Menow, Editor
Green Bay Sports Monthly
111 Lombardi Ave.
Green Bay, WI 54302
If you have an “in” as Nick White mentioned earlier, you probably want to make that known up top. If not, some standard information about who you are and why you matter will work:



I wanted to reach out to you about a story I think your readers would like. Our previous collaborations on “What happened to the Kicking Zendejas brothers?” piece last year and the review of “Five Packer-friendly churches in Green Bay” last month drew a lot of readers to your site.


After that, you want to make a quick and simple pitch on the topic:


Here’s the pitch: As you know, this is the 50th anniversary of the famed “Ice Bowl” game, in which the weather and frozen field conditions took center stage. It seems that every aspect of this game has been examined except for one: The field.

Every Packer fan knows Vince Lombardi spent $80,000 on an “electric blanket” of wires that ran under Lambeau Field to prevent the field from freezing. What they don’t know is the back story of George J. Halas, the nephew of Chicago’s famed George S. Halas, who sold the project to Lombardi. They also don’t know that this “malfunctioning” system actually served the city for more than 30 years and had been installed in several other stadiums successfully.


After that, you want to explain what you are proposing and why you are the person to do it:

I am proposing a 1,200-word piece for your December issue that digs deep on this issue. This piece will examine the “frozen tundra” in a way that gives context to the game, the field and the people involved the area’s most exalted patch of grass.

Although George J. Halas is gone, I have already spoken to his son, Tim, who is willing to share his recollections and his father’s notes with me on this issue. I also have access to three other GE workers who were responsible for selling and installing these systems back in the late 1960s and early 1970s to help me explain how this should have worked and why it didn’t during the Ice Bowl. Furthermore, the Packers have offered to let me spend time with current groundskeepers to see how things now work to provide context. They have also offered me access to their photo archives for images of the installation and the game itself.


Finally, offer them the ability to contact you if they are interested:

If this sounds like a good idea to you, please email me at (EMAIL) and let me know what you think.


Vince Filak


After the pitch

Once you make your pitch, the ball is solidly in the court of the publication. This can lead to additional anxiety if your story is based on a timely news peg that could be rapidly deteriorating as you wait to hear back. It can also feel like an eternity if you aren’t hearing back from multiple editors on multiple pitches.

Rehagen said there is a healthy debate among his friends who freelance regarding the idea of trying to expedite the process of acceptance by pitching a story to multiple places at once, something he said he doesn’t do.

“It’s not only excruciating waiting for a response from an editor, but it can also be a matter of losing a timely story,” he said. “But I still err on the side of caution—I just can’t imagine having an editor finally say “yes” and me having to tell them, “Sorry, I sold it elsewhere.” But I often wonder whether I’m being too cautious.”

After the long wait, you will end up with one of two potential outcomes from a pitch: You sell the story to the outlet or you don’t. Let’s consider each of these in turn and what it means:


Your pitch worked!

Nothing compares with the feeling of victory, so when someone gets your pitch and says, “This looks great! Let’s do it!” go ahead and enjoy a brief moment of exhilaration. After that passes, you need to consider a few things before you start working for your latest employer:


Clarify the expectations: The pitch itself should have established the foundation for what you will be doing for the publication. However, before you start working on the story, you need to make sure you and your editor are on the same page when it comes to the big issues. How long will the story be? What does the deadline structure look like? Where in the process will the editor get involved? Who has final say over specific elements of the story? If you have worked with the editor before, much of this will be old hat. However, if you are working with someone for the first time, getting this all set up and written out will be beneficial for both of you.


Show me the money: You are setting up a contract with a company to provide a service at a cost. Keep that in mind when you start looking into how much you are willing to ask for and what it is these organizations are willing to pay you. It might not be as easy to see it this way with freelance writing as it would be for other forms of projects that yield a more concrete product, but the situations are comparable.

“Rate is a big deal,” Rehagen said. “There is a rash of publishers who somehow think we should do our job for nothing or next to it. (No way.)  We have a skill that has value. You need to maximize that value—not just for yourself, but for your fellow freelancers.”

How that rate is established will determine the degree to which you are doing well financially or struggling as a freelancer. Some places will pay a certain amount of money per word, with a specific word limit on a piece. Others will offer to pay a flat fee for a story that fits within a word-count range. Other ways of establishing this also exist, but you can’t just think about the amount of time and energy associated with the writing of the story.

Reporting takes time and often cost money. In some cases, a story can be nailed down with a few phone calls and a few in-person interviews with someone nearby. In other cases, you end up going halfway around the world, like Choi did when he went to Russia, Morocco and the South Pole to conduct his reporting. (“I love traveling, and have been to all seven continents and on multiple archaeological and paleontology digs,” he noted.)

Money might not be the only motivating factor, as Choi noted while explaining how he sometimes considers the value of a job in other ways.

“There are other factors when it comes to whom I pitch stories to, such as prestige,” he said. “Writing for The New York Times may not be a great return on investment, but it’s great publicity and helps me get other jobs, and I treat such gigs like paying for advertising.”

However you calculate the value, be it in cash or other ways, figure out what you are earning from each gig and get it in writing.


Know your rights: Depending on the circumstances, the rights you have to the material may be more valuable than the cash you get from a particular piece. Many publications have moved toward a “work for hire” model in which they can do whatever they want with your piece as long as they want. This limits you in a lot of ways, so be careful with the fine print in the contract before you sign it.

“Ideally, as a freelancer, when you sign a contract, you get rights back to your story after, say, 90 days,” Choi said. “That way you can resell stories in, say, foreign markets, or if stories get collected in books.”

In some cases, you may care a little less about your rights than a paycheck, but you never know when an article could lead to a bigger project. A number of movies and TV series came from a single article. For example, “Shattered Glass” began as an article written by Buzz Bissinger.

“You need to read your contracts carefully. Ideally, you want the rights to your stories—so if Hollywood or Netflix comes calling, you can reap the benefits, but also, and more practically, so you can reprint it elsewhere and spin off for other stories,” Rehagen said.

Even if a big-name organization doesn’t come calling, retaining as many rights as you can to your material will allow you to control how your work gets used or reused. In a “work for hire” situation, you lose the ability to say “no” if you don’t like how the organization is using your material or what other projects are underway based on it.

“The area of concern in this area has always been owning the content — think of it as Michael Jackson buying the rights to The Beatles’ publishing to retain the wealth of many resells and replays of The Beatles’ songs, even though The Beatles are the authors,” White said. “Every single contract you will sign to work for a media outlet will give all ownership to the outlet, not to mention a possible NDA so that essentially the experience is “owned.” Retaining ownership rights, with some exceptions, will only belong to you if you start an outlet or buy it as an investor; otherwise, rights generally belong to the outlet.”


Dealing with rejection

Nobody likes hearing, “Sorry, not interested” when it comes to a story, but for freelancers, this can be particularly problematic. Finding a balance between investing in a story and overly investing in a story can be crucial to keeping your head above water, Rehagen said.

“I often do a little reporting to flesh out my pitch—but I don’t know anyone who does the entire story on spec,” he said. “It’s just not feasible to front that time, money, and energy without knowing if you’ll ever get paid or published.”

A lost opportunity to publish a story means a loss of time, energy and wages. This is why it doesn’t pay to have the story completed before you pitch it.

“I never pitch completed stories to outlets if I can help it for two reasons,” Choi said. “First, no outlet may end up picking up the story, and if that happens I will have wasted time and effort for no reason and I will likely disappoint the sources I interviewed, potentially burning bridges for later stories. Second, every outlet has a unique voice, and a story written with one story in mind may need to be drastically rewritten if pitched to a different outlet.”

Here are some ways to deal with rejection in a positive way that could still yield a good story:


Is the pitch “mostly dead” or just dead?: Remember Billy Crystal’s character in the Princess Bride? He’s talking to Mandy Patinkin about the dead guy on the table and he says, “He’s not dead. He’s only mostly dead.”

The same level of absurdity applies to your work. After it’s been rejected, you need to see if your work is dead or mostly dead when it comes to the pitch.

Dead is when the editor says, “This just isn’t something we want. Best of luck elsewhere.” At that point, you can give up on that outlet and look elsewhere.

“Mostly dead” is where the editor gives you a second bite at the apple. The editor might want to see more material before committing or might want to postpone the story for a good reason while still retaining interest in it. When you get a “mostly dead” response, see what constructive criticism you get from the rejection, determine how easy it will be to deal with that criticism and see if it’s something you want to do. If it’s a set of simple fixes for an editor who has been good about taking your work before, give it a shot and see if you can get an acceptance. If it requires you to do something you are unable or unwilling to do, consider other options.


Hope for the best but plan for the worst: When you pitch an article to a media outlet, you clearly hope the editor will love it and buy it on the spot. However, since you can’t rely on that outcome always happening, you want to have a back-up plan (or four) so that your initial work on the story doesn’t go to waste.

As Choi said throughout this series, working in a niche has many benefits: You become an expert on the area, you become the go-to writer on those topics and you work repeatedly with certain editors. One other benefit is that you know multiple outlets that want stories like the one you are pitching at that point. Therefore, if Magazine X decides the story doesn’t sound all that great, you can see if any of the criticism in the rejection merits addressing, spruce up your pitch and send it to Magazine Y.


Know when to stop: The late actor and comedian W.C. Fields famously once said, “If at first you don’t succeed, try, try again. Then quit. There’s no use in being a damned fool about it.” That’s some pretty solid advice when it comes to pitching a story.

You might really have an emotional attachment or a driving desire to see a particular story get published and that’s great. However, you have to remember you also have a passion for making rent and eating food, so you need to put your time and energy where it will help you meet those needs. You can give a pitch a few shots, but if you keep getting rejected and you can’t seem to make the editors want it, consider that you might be wrong about how important this thing is and then move on.

(Continue to Part III)

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