👩🏻Where Rory Gilmore Would Be Today: My Honest Prediction
I actually don't think Rory Gilmore would be much different from the rest of us readers and writers today. Here's why. Also go behind the scenes of my writing life as proof of my hypothesis.
The original Gilmore Girls series projected Rory as an intellectual unicorn—the kind of teen who takes a book with her everywhere as habit.
But by the end of the first seven seasons in 2007, the oh, so perfectly constructed foundation she built for her budding career already started to crack. (In the famous words of Jess Mariano: “Why did you drop out of Yale?!”)
About a decade later, Netflix’s 2016 A Year in the Life reunited us with a thirtysomething Rory who felt more like a lost bird. With only one hit article to her name, she bumbled through job interviews and men, including her engaged ex, without much footing on that foundation at all.
Then, she found her way back to it: a room of her own to write her story. The Gilmore Girls without the “the.” And it seemed all would end well in Stars Hollow. But would it, really? Especially after those famous final four words?
My Prediction: Rory Gilmore Would Be a Substack Writer Like So Many of Us Today
Now, as we read the books Rory Gilmore read for our Rory Gilmore reading challenge, with a featured focus on A Room of One’s Own by Virginia Woolf, I’m sharing why I think Rory would be right here on Substack today, after settling into her own room to write a decade earlier.
Despite a strong start in life, Rory Gilmore faced a myriad of career obstacles that are not uncommon to adult writers like herself:
Rory Gilmore Syndrome
“Rory Gilmore syndrome” a/k/a gifted kid syndrome is a pattern where naturally smart children are praised, then struggle with perfectionism, burnout, or avoiding challenges that don’t come easily. Having graduated as valedictorian from Chilton Prep School, then dropped out of Yale, and later published only one hit article, Rory Gilmore from Gilmore Girls is often considered the poster child for this. It’s especially true for millennials like Rory, who experienced the Great Recession early in their careers.
More Challenges
Millennial midlife crisis: the dissatisfaction millennials feel when their adult lives don’t match the stability or success they expected by this stage, particularly after having been promised they could achieve anything through education and hard work. It often involves burnout, financial stress, career uncertainty, or questioning identity and purpose.
The decline of traditional media (gift link): the shrinking influence and revenue of outlets like print newspapers and magazines. This shift has changed how people consume information, disrupted old business models, and increased competition for attention online.
And while A Year in the Life gave Rory’s writing a heartwarming arc set to the familiar hum of the “la las,” I find it unlikely she’d be anywhere but here on Substack, like me, and like other readers and writers, a decade later.
Why? First, the average advance for a debut author is only $57,000. The warm, fuzzy feelings publication brings do not have many dollar signs attached to them for most, particularly when stretched over years of writing and marketing.
Realistically, I envision Rory Gilmore as a single mom, like her mom, today. Perhaps she used her book advance as a down payment on a modest Stars Hollow home near her mom for help with the baby, but only pre-pandemic, when they were affordable.
Logan would be involved, but still with Odette. Rory would grapple with accepting large amounts of money from him or her grandmother, but for something like, you guessed it, tuition.
She’d be working at the Stars Hollow Gazette, but it wouldn’t be “enough” creatively or financially. She’d also need to market her book in a way that felt aligned with her bookish nature. So, where would she turn? Substack.
I Get It, Rory!
Here on Substack, I have branded myself as a “real-life Rory Gilmore.” While I’m not a mom, I do share much of Rory’s education and career trajectory.
An early and avid reader and straight-A student Rory’s age, I first won a citywide essay competition at age 8. I’ve been blogging since before it had a name, but was just a blue screen with a cursor.
I was named the top literary arts student in my high school class, then continued to refine my writing through law school and lawyering until it really took off.
By 2022, my blogging income fully sustained me, mostly through display ads and affiliate income from search engine-optimized content. So, I quit law and chugged full steam ahead on writing, having made it.
That is, until artificial intelligence changed everything. All of a sudden, chatbots and AI overviews spit out all of my work before anyone ever visited my site (thus, completely impeding my ability to earn from it). And social media transformed from helpful and communal to sloppy and toxic.
Which brought me here to Substack—a place where long-form content thrives and is made possible by the generosity of paid subscribers who value it.
But, like the more realistic arc I gave Rory since A Year in the Life, I want to keep my own arc real:
Writing is hard work, and earning from it is even harder. Substack enables it, but that’s only the first step, particularly when the general public expects free written content.
Inspired by Rory: My Room to Write
That’s why I’m starting a new section of this Substack called Room to Write. As your own real-life Rory Gilmore, it’s time for me to branch out from reading and living like a Gilmore to include writing like a Gilmore, too.
In A Room of One's Own, Virginia Woolf said, "A woman must have money and a room of her own if she is to write[.]" Nearly a century later, Rory Gilmore found her own room to write on the reboot of Gilmore Girls. And in Room to Write, I'm going behind-the-scenes on mine.
I’ll share the highs, lows, and messy middles I've lived through as a former lawyer turned full-time writer. I'm building in public on Substack, sharing the most and least impactful strategies I've implemented, and keeping it authentic and transparent along the way.
What will this look like? The whys and hows behind the scenes of what I’m working on, from creating a writing portfolio to self-publishing a book, and practical writing advice, for a few examples. I’m currently looking at a cadence of 1-2 times per month.
Some may find it interesting, others will find it really useful. I’ve experienced a lot!
However, if you love our Gilmore Girls book club, but writing advice isn’t for you, you can manage your subscription here. Your Substack account settings for the Friday Night Readers Substack publication allow you to toggle the Room to Write section on or off. So, feel free to choose your own adventure around here!
Friday Night Readers is a virtual, email newsletter-based book club that helps you read and live like the Gilmore Girls. Subscribe now, and you’ll instantly receive a printable PDF checklist of the 475+ books on the show—each one personally verified by me, your real-life Rory Gilmore, for you. Upgrade to get the checklist with episodes, plus exclusive posts and full community access to me.
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totally agree with all of your assumptions. Because, in reality, there are MANY exceptionally smart people that don't have exceptional success.
I agree that Rory would be struggling with trying to find her passion in writing if we followed her 10 years later (can't believe it has been that long).