“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. (Disclosure: Any link below with an * is an affiliate link, which means I will earn a small commission if you click through and make a purchase.)

When I decided two years ago to become a full-time freelance writer, I was overwhelmed by the possibilities. I didn’t know where to begin. Who knew there were so many options? Social Media Content Creator is a thing? What the hell is SEO??

I spent months Googling the topic, eventually homing in on the writing I wanted to do (personal essays, articles, blog posts) vs. what I didn’t want to do (copywriting, sales, marketing). From there, I ordered books on how to write, pitch ideas, and launch a freelance writing career:

• The Essential Guide to Freelance Writing by Zachary Petit

• Writer’s Digest Guide to Magazine Article Writing* by Kerrie Flanagan

• Writer’s Market: The Most Trusted Guide to Getting Published*

• On Writing* by Stephen King

The books offered useful nuggets of information, but they couldn’t provide one important thing: a portfolio. To get published, I needed to have a place to show off my work. That’s where Medium came in.

I began publishing pieces on my Medium page in June 2018. They ranged from silly listicles to “go get ’em, tiger!” blog posts. I wrote about writing and my kid and chronic illness. I became a “Top Writer” in Advice and Parenting. I gained followers. I published often and promoted the hell out of my work.

And the entire time, I had one goal: To have my work published in a major publication.

The Big Dogs

No offense to Medium, but the platform isn’t super impressive to editors. Anyone, anywhere, can post anything on the site. Unless you’ve been published in one of the newer Medium-owned pubs (such as Zora, Forge, or GEN), your work has most likely not been edited or vetted by a professional. It’s really no different than putting your writing up on your own blog.

My goal all along was to aim for magazines and newspapers that would make my parents proud. I wanted to see my writing in print. I wanted to work with a professional editor who would push me to write better than I’d ever written before. I wanted to challenge myself to pitch to as many major publications as possible and to garner hundreds of rejections a year. (Remember: The more you’re rejected, the more your work is getting out there. Never see rejection as a sign to quit, but as a challenge to keep trying.)

I wrote up a list of publications I wanted to work for and studied what they published. And when I saw that my hometown paper, The Boston Globe, prints 650-word essays in their Sunday Magazine, I knew I had to give it a shot.

The Story

For months I’d been tweaking an essay I’d written about my son at a baseball game. The piece was short — 700 or so words — and touching, ending with the realization that although my wiggle-worm child couldn’t follow his coach’s instructions during a game, he had so many other incredible qualities to offer.

I’d planned to put the piece up on Medium, as I had with all my other work. But then I realized that if I continued to post everything on Medium, I’d never achieve my bigger goals. So I did a Google search on where to publish short personal essays and came across a blurb about The Boston Globe Magazine’s “Connections” column.

The Globe describes the column as “a 650-word first-person essay on relationships of any kind (romantic as well as those between friends, siblings, and parents and children).” My piece felt like a good fit, so once I felt it was ready, I sent it out.

The Submission

I was submitting this piece in-full (rather than as a pitch), so I kept the email short and sweet. I’d read somewhere that you don’t want to recap your entire essay for the editor, so I simply wrote:

“Pasted below is a 683-word personal essay for Boston Globe Magazine’s Connections column. The piece reflects upon my relationship with my young son and the moment I stopped trying to force him to be something other than his loving, free-spirited self.

A Boston native, I currently reside in New York, where I write short fiction and personal essays.

Thank you for your consideration of my piece. I look forward to hearing from you soon.”

I then included a link to my website (which at that point only had copies of my Medium posts), pasted the essay into the body of the email, hit send, and crossed my fingers.

Two days later, I got a yes.

The Acceptance

An editor from the Globe wrote to say that they wanted to publish my piece and would pay $500.

FIVE.

HUNDRED.

DOLLARS.

That’s a great rate for an essay, especially one under 700 words. In addition, the piece would appear in print and online.

I grew up within walking distance of the Globe, so getting my first print byline in this paper was HUGE. I could not have asked for a better first acceptance.

The Piece

It took four months for the Globe to publish the essay and another 30 days to pay me. (That’s the one downside of print publications: everything moves slowly.) But it was worth it.

On March 24, 2019, my husband, son, and I got up early and drove to the nearest newsstand to buy copies of the paper. And there, on the last page of the Sunday Magazine, was my essay.

Lessons Learned

What I’d love for you to take away from all this:

1. Don’t be afraid to aim high. The worst that will happen is you get a no or you don’t hear back at all.

2. Use Medium or a personal blog to build up a portfolio. You can’t get published without showing an editor your work, but you can’t show your work until you get published. What’s a writer to do? Post your writing to Medium or to your own blog so you’ll have something to share with editors when you pitch an idea or submit a story. At the end of the day, all the editor really wants to see is that you know how to write and to get a sense of your voice.

3. Keep at it. Keep writing, keep pitching, keep submitting. The more you do it, the better you’ll get and the higher your chances of being published.

I hope this provided some helpful info! If you’re interested, you can read my essay on The Boston Globe’s website.

A version of this post also appears on Medium