“The Story Behind the Story” is a behind-the-scenes series on the essays and articles I’ve published in various outlets. By sharing information on pitches, rejections, and lessons learned (all the information I wish I’d had when I was starting out), I hope to help other writers who are trying to establish a successful writing career.

I love my freelance writing job. It’s exhausting and stressful and the pay is terrible, but man, are there some perks. Like that time I got to interview my idol of many decades for a story in a national publication and then her team promoted the piece all over social media? Yeah, that was pretty incredible.

Let me back up a bit: For 25 years, I’ve been a massive fan of singer/songwriter Ani DiFranco. I’ve seen her in concert dozens of times. Her posters adorn the walls of my home office. I own every recording she’s released and could easily talk your ear off about her life, her music, or her activism.

But, never, ever did I expect to spend 40 minutes on the phone with her.

The Idea

Because I’m a fanatic, I know that November 2020 is the 30th anniversary of her eponymous debut. I also know she has a new Patreon account and recently launched a digital radio station.

I wanted to write about these various projects, but didn’t know what the angle should be. A Buzzfeed-esque list of “Essential Ani DiFranco Songs”? A personal essay about the impact her music has had on my life? None of my ideas felt quite right.

It was especially difficult because, like much of the world, my life screeched to a halt in March. Thanks to COVID-19, my son’s school closed, my husband’s office moved to our basement, and my ability to write a coherent sentence went out the window. (Not that it really mattered. Most publications — at least, those that were still around — had no budget to hire freelancers.)

I didn’t write anything for a long while, but in May I forced myself to pull together a couple of half-brained pitches, just to get something out into the world. Just to feel like myself again. As I sat at my laptop, trying to brainstorm a DiFranco-related idea to send to editors, it hit me: Why not just…ask to interview her? The worst thing that would happen is that I’d get a no — or, more likely, no response.

Before I could talk myself out of this insane plan, I drafted a quick email to her publicist:

I’m a freelance writer based in upstate NY. I’ve been following Ani DiFranco’s music and career since the mid-90s. I’d love to write a piece on the upcoming 30th anniversary of her debut album, as well as all the many projects she’s been working on (Patreon, The Prison Music Project, Righteous Babe Radio…). Would it be possible to schedule a phone or Zoom interview with her to discuss the anniversary as well as her current work?

I don’t have a confirmed publication at this time; I wanted to reach out to you to gauge interest. If it’s possible to schedule the interview, I have a number of outlets in mind.

Thanks very much for your time and consideration. I look forward to hearing from you.

I located the publicist’s contact info and sent it off, fully expecting not to hear back.

But, two days later, she responded.

With a yes.

The Pitch

Now came the hard part: Getting a publication to accept the idea.

I reached out to a ton of places and was heartbroken when the rejections started pouring in. Rejections are by no means uncommon in this weird freelancing job of mine, but I was so worried I wouldn’t get an assignment and therefore wouldn’t have the chance to do the interview. I was thisclose to speaking with an artist I’d been a fan of for so long, and now it might not happen!

But I was determined. With each “no,” I tweaked the pitch and sent it right back out. It was like an email boomerang. It came back to me and I threw it right back into the world.

Somewhere during this time I saw on Twitter that the arts editor from Shondaland was open to receiving pitches. So I sent her the following email:

I hope all is well. I’m writing with a timely music pitch that I hope you’ll consider for Shondaland.

On June 5th, Righteous Babe Records, the indie label founded by singer/songwriter Ani DiFranco, will release Long Time Gone from The Prison Music Project — a collective of singers, producers, artists, and musicians who aim to reflect the shared humanity of people on both sides of prison bars. The album, produced by DiFranco and musician Zoe Boekbinder, features works by incarcerated writers and musicians from New Folsom prison in Folsom, California, and includes performances by DiFranco, Boekbinder, Amanda Palmer, and Princess Shaw, among others.

Long Time Gone, an album 10 years in the making, aligns solidly with DiFranco’s years of activism through music. She has agreed to sit for an interview with me to discuss the album, her 30 years in the industry, and the other various projects she’s focusing on at the moment. Do you think an article based on the interview would be a good fit for Shondaland?

About me: I’m a freelancer based in New York. My work has appeared in FLOOD Magazine, The Boston Globe, Greatist, The Girlfriend from AARP, Brevity, and Disrupt Aging from AARP, among others. I have a piece forthcoming in The Washington Post.

Thanks very much for your time and consideration.

In all, this was one of 17 pitches that I sent out for the piece.

A few days later, I got a response. This time, finally, it was a yes! Shondaland was going to publish my interview.

The Writing

After many weeks of emailing back and forth with DiFranco’s publicist, we were finally able to schedule a time for the call. To say I was nervous as hell would be an understatement. In fact, once the call was on the books, I spent 24 hours wondering what the hell I was thinking when I came up with this idea. I felt inadequate. Stupid. A big giant imposter who was just waiting to be found out.

Thankfully, the feeling passed. And on Friday, June 26th, I spent 40 minutes chatting with my idol of many years. She was incredibly kind, funny, easygoing, and smart. We talked about politics, music, art, activism, and family. And I’m so glad I recorded the call (which I always do during interviews) because I honestly think that without the recording I wouldn’t believe the call had happened at all.

I spent the next week transcribing our conversation and writing up the article. The hardest part about Q&As is, by far, editing. I had something like 6,000 words in the transcript and my editor wanted the entire final piece — including the intro paragraphs — to be around 1,200 words. It took many hours trying to figure out what to keep and what to delete, but I knew I wanted the article to focus on three main things: The Prison Music Project album (released in June), DiFranco’s current projects (the radio station, her upcoming studio album, Patreon), and the 30th anniversary of her debut. With those as my guide, I was able to cut away all chatter about other topics and focus on what I thought was most important for the piece.

After about a week of writing, I submitted the draft to my editor and the article was published in full, with no edits, on August 25th. Within a few days, DiFranco’s team had promoted it on Twitter, Instagram, and Facebook, which I like to think means that they were happy with the final results.

If you’re interested, you can read the finished piece on Shondaland.

Lessons Learned

The biggest thing to take away from all this: DREAM BIG.

I can’t tell you the number of times I’ve come up with an idea to pitch to an editor, and then promptly talked myself out of it. “I’m not smart/knowledgeable/experienced enough to pitch that story. They’ll laugh at me. They’ll know I’m incapable.” All of which is ridiculous. Sure, I probably shouldn’t pitch a white paper on neuroscience to an academic journal — that’s a bit out of my wheelhouse — but there’s no reason to think that I can’t write an article for a traditional newspaper or magazine on a subject that interests me.

And the same goes for you: If there’s something you want to write, come up with the angle. Figure out how you’ll tackle the story. And pitch that to the editor. The worst thing that might happen is you’ll get a no. So what? You move on. You tweak that pitch and send it elsewhere. The best thing that might happen is you get a yes and then you get to interview someone you’ve been dying to speak with.

But when those moments of doubt creep in and you’re not sure if you should tell anyone about your crazy idea, just remember what a wise woman once said:

“Alla this was just someone’s idea, it could just as well be mine.”

A version of this post also appears on Medium