Tim Herrera had a dream job. As writer and editor for Smarter Living at The New York Times, he oversaw one of the most popular columns at the legendary Gray Lady. But after five years at the top, he surprised everyone and quit.
I just got super, super burned out," he told me during our podcast interview on Write About Now. "I was having such a rough time with the pandemic a year and a half in, so I just kind of needed to take a break, get off the mountain for a little bit."
After taking a "mental health break," Tim decided to do what so many are doing in The Great Resignation—work for himself. He launched the Freelancing with Tim newsletter and zoom panels, dispensing much-needed advice for forlorn freelance journalists on everything from pitching editors to being a writer editors don’t want to assassinate.
"When I was an editor at the Times, probably 85% of the work I was editing was from freelancers. So it felt like a good opportunity to give back to that community," Tim says.
Give back he does. I affectionately call him the Freelance Oracle for the knowledge and wisdom he spreads, and I wish I had a resource like Tim back during my time in the trenches of the freelance Great War.
In our podcast interview, we talk at great length about what he's learned editing so many writers over the years, including vetting the 700 pitches he used to receive at the Times every week.
Being the receiving end of so many proposals, Tim has devised 4 Unbreakable Rules of Pitching, which I think are very wise and will share here for posterity.
Never ever send a full draft of a story to an editor. The only exception here is sending an opinion piece or a personal essay. The reason? "When editors see a complete draft, we think to ourselves; this person's done the story. It's take it or leave it," Tim says.
Always structure your subject line in an email as follows.
"Freelance pitch: Title of the story."
This simple formula makes your message clear and easy for the editor to understand.
Always include clips and bio with your pitch. You don't have to overwhelm with your entire canon. Three or four recent clips relevant to the story you're pitching will suffice.
Double-check the small things. Run your pitch through Grammarly to check for typos, read it aloud, or do both. Make sure you address the right publication and the right editor in your pitch. Make sure your links go where they should. Oh, and this is a common error: Make sure the publication didn't just run a similar story.
And don't give up on your writing dream, even if you get rejected. You never know where your career may take you.
Subscribe to the Write About Now Podcast here.