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Lessons for freelance writers

Here's what this veteran freelancer learned after offering to help other writers with their careers.

A veteran writer shares his top lessons for freelance writers.
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In early November, I tweeted an offer to help writers who had been approached by Deadspin after the staff quit in protest over the new ownership’s quest to turn the snarky and smart sports blog into a box score with looser language and wire photos. Freelancers were targeted to pick up the slack. Writer Alan Goldsher contributed one piece to zombie Deadspin – and got vilified by writers and fans. Almost immediately, he resigned.

Goldsher, in a series of heartfelt tweets, apologized for his lapse in judgment. In one post, the veteran freelance writer mentioned that he “never had ANY significant support from colleagues.” I took Goldsher’s comment to mean throughout his career, which made me shudder. It’s not that bad, I thought, so I decided I’d offer to provide an editor’s email address or two to freelancers who had been approached by Deadspin or had considered writing there. It’d be a small gesture of support for a site I loved, and it would keep writers from having to sell their integrity for a byline and a few bucks.

The tweet garnered 1,300 retweets and 2,700 likes. I answered around 30 messages.

I was thrilled to help, even if many of the writers who contacted me hadn’t been approached by Deadspin – or didn’t need my assistance. The impression I got reading the messages was that many of these writers felt overwhelmed. You can learn how to write, but relatively few resources exist on how to survive – let alone thrive in – the freelance life.

Those email addresses are worthless if certain writers don’t embrace certain lessons. Here’s what I want to pass on from my short stint as a connector.


Your name is your most valuable asset. One writer with an extensive, accomplished resume asked me if I knew anyone at G/O Media, Deadspin’s new owners. He needed money and wanted to work there. I spent a good three emails attempting to dissuade the poor soul to stay away. If word got out that he was on staff, his name would be radioactive to a wide swath of writers and editors for years. I’m not sure what he decided to do, but I hope he made the best long-term decision.

Other gigs exist. Someone always wants a capable writer. But a large part of freelance writing involves not writing. And when you do write, it’s the most pedestrian content – letters of introduction, reminders to old editors, pitches. You cannot simply wait for gigs to arrive. If I could eliminate administrative tasks, I’d have filed this column last week.

Follow up. I had one writer ask me to send him contacts. I politely declined to send anything without knowing his interests. He could have taken two minutes to respond with said interests. He never did. The difference between good writers and everyone else is clear: Good writers seize opportunities; bad ones wait for them to be presented on a platter.


Don’t rely on formality. A few people asked me if I knew any editors who were taking pitches. It doesn’t matter. If I believe in my idea and have a plan in place to execute it as a story, I’m sending my pitch. The worst thing an editor can do is ignore the email. One writer said he was nervous to approach national publications. Again, if your idea is good, you can take it anywhere. If you are nervous, perhaps that story isn’t sound as you originally envisioned.

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Ask for one favor only – and make it relevant. I had one writer also ask how to write a pitch letter. I had another ask if I could recommend him to editors. These weren’t part of my original offer. Favors like these have two deleterious effects. First, they make the benefactor decline to help you later. Second, your irritating request might make them think twice about helping others in the future. 


Have patience with editors. I sent the Tweet on Friday. The messages piled and piled. Sunday was awful. I had a deadline Monday. Plus, an article posting Monday needed editing Sunday night into early Monday morning. I was trying to finalize edits on my book. Though I wanted to respond to everyone immediately, I simply didn’t have the spare hours. Sunday was an onslaught; Monday I rested. On both days, my daughter was up before dawn. The messages sat until I summoned the energy on Tuesday morning to care again.

I can’t comprehend how editors deal with this level of email inundation on a daily basis. My trial run was overwhelming. I truly realized that editors are not callous or don’t care about your pitch. They just don’t have the time. Cut them some slack.

Don’t network; build your army. Like most social media, Twitter is a wonderful self-promotional vehicle, but it’s also a wonderful way to connect with other writers and editors. It’s easier to ask a friend for help than a stranger.


There’s a whole world beyond social media. Ask your local library and bookstores about writers’ groups. Joining a national organization can be a great way to meet other writers. At the 2017 American Society of Journalists and Authors’ annual meeting in New York , I met a writer who also lived in Central New York. She invited me to join an email group of writers who regularly meet for lunch. I look forward to these get-togethers. I can bond with nice people over the banalities and triumphs of a lonely occupation.

Pay it forward. I ended nearly every correspondence with this. I have been a freelance writer for more than 13 years. I can’t remember competing with another writer over a story idea or a beat. There is no harm in helping a freelance writer who shares your interests. If someone beats me to a story, I’ll move on to another idea or find a different way to cover the topic.

That’s the practical reason.


Here’s the real reason. This is an occupation where the only sounds you hear some days are the tapping of the keyboard and the doubts rattling inside your head. The sturdiest soul grows weak under this arrangement. Knowing that you’re not alone, that someone wants to help, can provide immeasurable comfort.

Paying it forward costs nothing and means everything.



Ithaca-based Pete Croatto is a veteran freelance writer who has written for The New York Times, The Christian Science Monitor, Publishers Weekly, Columbia Journalism Review, and many other publications. He is also working on his first book. Twitter: @PeteCroatto.

Originally Published