Rory Gilmore’s freelance journalism lessons

In the much-anticipated Netflix revival of Gilmore Girls, thirty-something overachiever, Rory Gilmore, finally comes up against an obstacle she can’t quite tackle: freelance journalism.

Last we saw her in 2007, she was a fresh-faced Yale graduate, getting ready to hit the road and report on the Obama campaign.

Nine years later, however, she’s still struggling to make it out there in the writing world. Throughout the four-episode miniseries, Rory even comes up against three major career opportunities, but they all fall through — mostly through faults of her own.

Here’s where Rory went wrong, and what freelancers can learn from her.

Sign contracts up-front

Career opportunity #1: Ghostwriting a memoir for Naomi Shropshire

Rory put in at least five meetings in London with this woman, who vaguely described herself as a “hellion” with expertise in “feminism and environmentalism.” Still, she seemed to have zero interest in divulging any valuable information. Instead, Shropshire wasted their time by downing martinis and pitching bad ideas for children’s books. After a few months of these shenanigans, she finally decided to cut Rory off and ditch their partnership.

Rory received a call from Shropshire’s attorney:

“My firm is preparing paperwork you’ll soon receive,” he said, “dissolving the contract on your book project.”

“Let me save you some time. There is no contract,” Rory said. “I was doing this on spec, so there’s nothing to dissolve.”

Big mistake! Even if Rory was ready to let that job go, she should’ve been reimbursed for all of those meetings and all of that time spent overseas. And she could’ve been if she’d signed some papers up-front stipulating a kill fee or an hourly rate.

Embrace the startup world

Career opportunity #2: Taking an interview with Sandee Says

“We have no individual offices — not even me. We work best in a hive, buzzing around each other, making word honey.”

So said Sandee, the twenty-something, self-assured CEO of Sandee Says, a hip new website that publishes culture pieces.

At the ripe age of 32, and with a piece already published in The New Yorker, Rory evidently felt above this position — so much so that she didn’t even prepare any pitches for her interview.

What Rory didn’t realize, however, is that startups are great places to learn new skills, make yourself needed, and hoard free snacks. Especially since the CEO sought her ought, Rory had an opportunity to carve out her beat, refine her voice, and basically write whatever she wanted. Instead, she lost out on the job and was sent back to the drawing board.

Take the boring assignment — and don’t stop after you sleep with the Wookiee

Career opportunity #3: Writing an article for GQ

After several postponed meetings with Condé Nast, Rory finally got a foot in the door. Her big scoop? Writing about lines — yes, lines — like lines of people waiting for cronuts, new Nikes, and video game releases.

OK, no one really wants to write about lines, but it’s an opportunity to be published in GQ! And Rory knew that. So she took the project, stood on a few of these scintillating lines, and interviewed some interesting characters.

Good going so far, right?

That is…until Rory sleeps with a guy dressed as a Wookiee, has a mini meltdown, and ditches the assignment.


Freak-outs are fine (expected, almost) but you don’t just quit! She should’ve taken that project and found a way to shine, even if they’d asked her to write about toilet bowls at gas stations.

As any freelancer knows, sometimes you have to take on those boring assignments and muddle through that grunt work — at least until you get back on your feet and can start firing off those New Yorker pitches again.

What Rory did right

Despite her faults, Rory did some things right. She really hounded Condé Nast for that interview. She used her connections to get what she wanted. And most importantly, she found her niche.

After all, she eventually decided to jumpstart her town’s outdated newspaper, The Stars Hollow Gazette, despite pushback from the traditionalist community. It was during this process, however, that Rory finally landed on her true calling: book writing. Yes, she’s going to write a book titled, Gilmore Girls, about her mom and herself.

That’s cute and all, but again, what happened to Rory’s promising career in journalism? What happened to worshipping Christiane Amanpour? What happened to those nine years of freelancing? HOW IS THIS GIRL GONNA MAKE MONEY?

If Rory decides to continue pursuing this career path, hopefully she’s able to take some of these lessons in stride. At the very least, when someone inevitably interviews her about her bestselling book, Gilmore Girls, she can be a nicer mentor than Naomi Shropshire was.