Welcome to The Freelance Life

[Announcing a new monthly column, The Freelance Life, by Ethan Gilsdorf, about the trials, tribulations, triumphs --- and tips to share --- along the path to becoming a freelance writer. This fall, Ethan is launching a suite of classes at GrubStreet called the Freelance Essentials Series, which teaches students the skills and craft to become working freelance journalists.]

by Ethan Gilsdorf

Back in the 1990s, when I first contemplated becoming a freelance writer, I was green. OK, I was more than green. I was chartreuse. I was viridescent. I was so naive-green, it hurt to look at me.

But for some reason, that ignorance and naiveté served me well. Coming out of an MFA program in poetry -- a field known for launching lucrative writing careers --- I knew I was prepared for ... well ... I had no idea what I was prepared to do in life. But after some real-world experience working in a cutthroat bookstore and at a small hippy college as a PR flack, I was headed somewhere.

I knew how to write a poem, and a press release, and a cover letter. I had always been good at working on projects by myself, and finding that internal fire to keep moving forward. As a poet, I was already well-schooled in rejection. My skin was thick. I very much wanted to take myself seriously as a writer. And I wanted an audience of readers.

So, furtively at first, I began propose articles and essays. I aimed high: The New Yorker, Harper's (a tad too high, perhaps?). And low: my local food co-op newsletter. Guess where my first freelance piece was accepted? I believe that article was called "All About Tuna."

With that minuscule publishing success under my belt from which I slung my gun for hire, I aimed for the next target -- the next publication on my reality-based, not fantasy-based, list. I think it was a small fanzine about cartoons. With that experience, I pitched again. I reviewed a book about Elvis for a small daily newspaper in Baton Rouge, and I received a free copy of that book as payment. I continued.

I had never taken a journalism class, nor written for my college newspaper, and it showed. My early ideas for articles were poorly conceived. My pitch letters were amateurish. I had no idea what a "lede graf" (the lead paragraph) was. I was clueless about what editors really wanted. My ability to react quickly to timely events in the news was non-existent. As a freelance journalist, essayist, critic, whatever I was or wanted to be, I was absurdly unsophisticated and unworldly.

And yet, I stuck with it. I kept submitting my ideas and essays and articles. I lived abroad -- Paris, to be precise -- and I landed some lucky gigs. I somehow found myself writing 125 word capsule movie reviews for an English-language publication. That led to more book reviewing, then restaurant reviewing, then working for Fodor's travel guides as their hotel reviewer. After several years of small-scale results, I finally got some traction in this new field. On a lark, I pitched a crazy idea to The Boston Globe. They liked it. And I was off and running. Trial and error -- making more mistakes than I will admit to you here -- I began to carve out a small career as a freelance writer for publications that paid that people actually read.

This Gun For Hire Still 5Since those first steps, 15 years have passed. My ideas for articles, essays, columns and reviews have been rejected dozens and dozens of times by some of the nation's finest publications. They still are.

I've probably amassed more than 1,000 "no's."

Just last week, I had three article ideas shot down by editors with whom I have worked for years. Another friendly editor severely "reworked" my column. This summer, a prestigious publication accepted my idea for a column, and I excitedly wrote it up. Three months have passed since I last heard from this editor.

The struggle continues. The freelance life has its trials and tribulations, tremors of success and seismic cataclysms of defeat. I fret. I think, "I'll never think of another great idea again," or "I'll never write for XX publication again," or "I'll never make enough money to cover my rent," or "That editor must not like me."

And yet, in and around the rejection and competition, I find new hope, new ideas, new courage, new successes, and they come often enough to stave off my despair. I find new topics and stories to write about. I find new interests. I make new connections. I keep writing and, weirdly, keep barely making a living.

Oh, how I wish I had discovered a GrubStreet back when I was a newbie journalist. Maybe I'd have saved myself some frustration. Certainly, I would have learned some valuable skills: how to structure and craft various freelance pieces (opeds, personal essays, features, blogs); how to pitch and publish in legacy and new media; how to create an area of expertise and a platform; how to generate ideas and react quickly to breaking news; how to support a possible future nonfiction book project after publishing success and mastery of the fundamentals; and above all, how to develop good "freelance life" work habits to keep going.

All of this is the thinking behind a new series of classes I'm offering at GrubStreet, called the Freelance Essentials Series, which teaches students the skills and craft to become working freelance journalists. The Series begins with five classes this fall: a ten-week workshop called Writing and Pitching Essays, Op-eds, and Blogs for Publication (beginning Sept 16), and four one-time seminars: Nuts and Bolts for the Freelancer (Sept. 14), Writing Killer Pitch Letters (Oct. 11), Writing and Pitching the Op-Ed (Nov. 9), and Freelance Idea Clinic (Nov. 23). If y'all dig them, there will be more in the winter and spring.

Whether you are interested in full-time devotion to the freelance life, or part-time smaller steps, my hope is that some of these classes will help you land some assignments, get your work out there, and fulfill your dreams. And, I hope, avoid many of the boneheaded missteps I made as a beginner.

I hope to see you at GrubStreet this fall.



grubstreet Image
About the Author

A GrubStreet instructor since 2005, Ethan Gilsdorf is a journalist, memoirist, essayist, critic, poet, teacher, performer and nerd. He is the author of the travel memoir investigation Fantasy Freaks and Gaming Geeks: An Epic Quest for Reality Among Role Players, Online Gamers, and Other Dwellers of Imaginary Realms, named a Must-Read Book by the Massachusetts Book Awards. His essay "The Day My Mother Became a Stranger" was cited in the anthology Best American Essays 2016. His fiction, poetry and essays have appeared in Poetry, The Southern Review, The Quarterly, Exquisite Corpse, The North American Review, The Massachusetts Review, New York Quarterly and dozens of other literary magazines and in several anthologies, and he is the winner of the Hobblestock Peace Poetry Competition and the Esme Bradberry Contemporary Poets Prize. Gilsdorf got his start in journalism as a Paris-based travel writer and food and film critic for Time Out, Fodor's and the Washington Post. He has published hundreds of feature stories, essays, op-eds and reviews about the arts, pop, gaming and geek culture; and media and technology, and travel, in dozens of other publications worldwide including the New York Times, New York Times Book Review, Boston Globe, Boston Globe Magazine, Boston Magazine, Wired, Salon, WBUR's The Artery and Cognoscenti, Los Angeles Times, USA Today, and Art New England. A regular presenter, performer, and event moderator, he frequently appears on programs such as NPR, The Discovery Channel, PBS, CBC, BBC, and the Learning Channel, and also lectures at schools, universities, festivals, conventions, and conferences worldwide, including at this TEDx event, where he nerded out about D&D. Gilsdorf is co-founder of GrubStreet's Young Adult Writers Program (YAWP), and teaches creative writing at GrubStreet, where he served on the Board of Directors for 10 years. He teaches essay, memoir, journalism and other workshops, and is also the instructor of GrubStreet's 8-month Essay Incubator program and serves as coordinator of GrubStreet's Providence program. He’s also the lead instructor for the Westerly (RI) Memoir Project. He has led writing workshops for non-profit social justice organizations and also teaches writing and Dungeons & Dragons classes for younger students, in schools, libraries and community centers. He had also served on the Boston Book Festival Program Committee and as a member of the Boston Society of Film Critics. He received his BA from Hampshire College, and an MFA in Creative Writing from Louisiana State University. Follow Ethan’s adventures at or Twitter @ethanfreak, and read his posts on Grub's blog, GrubWrites.

See other articles by Ethan Gilsdorf