In the paradoxical world of freelance writing, your first few stories are essential. They’re also the most difficult to land because editors usually want to see previously published work (aka clips).

After all, they don’t know you yet. Clips are all they have to go on. Well, that and the pitch itself.

“It all comes together with the pitch,” said freelance writer Susan Shain.

In addition to contributing to The Penny Hoarder, Shain freelances for publications such as The New York Times, CNN Travel and NPR. She shared her insider tips with us.

“A lot of it is luck,” Shain said. “That’s important to keep in mind.”

Most of it? Persistence. There will be troves of rejections from editors — even the most successful writers get rejected constantly. It’s part of the trade, especially when you’re just starting out.

“Getting those first sales is the most difficult part of the journey,” said professor and author Rick Wilber. “You have to persist. It does get easier.”

Wilber taught magazine writing for 40 years. Now he is a genre fiction professor for Western Colorado University’s MFA program.

From story ideation to the pitch email, here’s what to expect on the (sometimes harrowing) road to publication. And, as with most crafts, you first have to master the rules of the road before you bend or break them.

An Idea Worth Pitching

Aha! You have a great idea. You’re amped and already envisioning the feature story on the cover of Time magazine, glistening in grocery store check-out aisles all across America.

Then you hop on Google to do some preliminary research, and your heart sinks. Time published that article two years ago! And so did Forbes and People and Inc. To add insult to injury? The Onion even spoofed it a couple times.

Loren Margolis, CEO of Training and Leadership Success, contributes thought leadership articles for publications like Forbes and The Muse. If you’ve thought of an idea, she said, it’s probably already on the internet multiple times. But that’s not necessarily a bad thing — it can actually help refine your idea.

“Do a search to see what angles, subtopics and viewpoints others have about it,” Margolis said. “If there is insight or information that someone has missed, bingo. You have a unique viewpoint.”

After you’ve found your unique viewpoint, do a little pre-reporting.

“Get in touch with a source,” Shain said. “Get a quote.”

But don’t do the full interview yet. Set expectations. Let the source know that you plan to pitch the story to a few publications or websites. (Having the source on board early will earn you a lot of brownie points with the editor later down the line.)

“Get the access first,” Wilber said. “Know you have the access, then use that as your tool for your pitch.”

But first you have to figure out where to pitch.

Submission Guidelines and Best Practices

At this point, you’ve refined your idea. You haven’t written the first draft yet, but you might have an outline. Now it’s time to find that potential story a good home.

“It’s your job to figure out what magazines [or publications] like those types of stories,” Wilber said.

Finding a good fit can be tricky. Luckily, Shain is also the founder of WhereToPitch.com, a website that helps people find appropriate publications for their stories. Another one of Shain’s go-to resources is WhoPaysWriters.com, a site that tells you which publications pay and how much compensation they offer.

Once you’ve narrowed down where you think your story is publishable, scour the publication’s website for submission details. And follow the submission guidelines exactly. They are there for a reason.

Sometimes the publication will have you submit your pitch via email with specific subject-line requirements. Sometimes — especially for literary magazines — the publication will have you send it through a portal called Submittable.

But most of the time, there won’t be much guidance at all. This is where a lot of guesswork comes into play, especially when finding the right editor’s email.

Many publications have a masthead section that lists the writers and editors, some more visible than others. You may also have to try the “Contact Us” section. Try your best to get a first and last name of someone in a relevant department. Ideally, you want to send your “How Yoga Helped Improve My Productivity at Work” pitch to the lifestyles editor and not Jessica from the public policy watchdog section.

Once you have a contact name, you’re on the right track. Shain recommended a tool called Hunter.io, a website that helps you guess or verify email addresses. For example, you could type in Adam Hardy and ThePennyHoarder.com. The website will generate its best guess, or it will give you a confirmed email address if that information is available.

If a certain editor’s email address is particularly difficult to track down, I’ve come up with a couple tricks of my own:

• Scroll to the bottom of the publication’s webpage to find a “Contact Us” or “Advertisement” section. They will likely have a “customerservice@domain.com” email readily available. Use that address to confirm the domain (i.e. what website you’re putting after the @ symbol).
• As mentioned above, find the applicable editor’s first and last name on the company’s masthead or the “Contact Us” section.
• Use the BCC email function to send as many first and last name combinations as you need.

But wait! Don’t hit send until you’ve crafted the perfect pitch.

The Art of The Pitch Email

The pitch email, more formally called the query letter, is where you lay it all out for an editor. There’s a lot to cover, but editors don’t have the time to read an email that’s as long as the article itself. Keep it concise.

In this email, you want to cover your story idea, the groundwork you have done with your sources, your experience and why your article is best suited for that specific publication. For new freelancers, the pitch email is the place where you can present your expertise even if you haven’t been published before.

By this time your idea should be fleshed out well. Most publications don’t require a full draft of the story until a deadline has been established, but Shain said be ready to write in case the editor asks for a draft of what you have so far.

She also recommended avoiding the phrase: “I’d like to explore…” Using language like that implies that you don’t have the answers.

And editors want the answers.

Also, Wilber said to avoid “teaching the editor.” Don’t over-explain yourself or your idea in the pitch. It’s a delicate balancing act that requires a few tries before you get the hang of it.

Over the years, Shain has fine-tuned her pitches. She likes to include a sentence to hook the editor in immediately. She skips pleasantries altogether and includes a catchy headline and a quote from a source during the pre-reporting stage.

Even so, she estimates her  pitch-to-acceptance ratio is about 1:10 to editors she doesn’t already write for.

“You can get rejection after rejection after rejection,” Shain said. “You wonder if you’re cut out for it.”

Wilber said that new freelancers should not only expect rejection but embrace it.

“Every time you get rejected, you have a choice to make: Quit or get better,” he said.

And even if your pitch does get accepted, that doesn’t necessarily mean your story will be published. Now you have to write it.

By Adam Hardy (@hardyjournalism)