I’m rewatching Gilmore Girls.

It’s been 21 years this October since the show, which centres on the intense mother-daughter relationship between Lorelai and Rory Gilmore, first aired. While I’m not ashamed to be rewatching a cult classic, I am grappling with a different creeping sense of shame. Am I Rory Gilmore?

Rory was the original burned out millennial. Born in the mid-80s, she was told she could do anything and was given every opportunity to realise that potential. And yet, she flounders. Repeatedly. Her most egregious character flaw, however, is her painful lack of self-awareness that frequently tips over into an inflated sense of self-importance (she once actually said, “I’m a Gilmore!”).

It’s in her work ethic that Rory, who wants to be a journalist and cites Christiane Amanpour as her career idol, puts her entitlement on full display. She expects to get a job at the New York Times straight out of college and thinks one New Yorker byline is enough of a CV to walk into any staff writer job without an interview. She’s a total brat. Or, as the writer Koty Neelis put it back in 2016: “She fucking sucks.”¹

Why am I so paranoid that I’m Rory? Because there have been plenty of points in my career in which I too have been a total brat. I cringe thinking about them now. I’m so embarrassed that rather than give specifics here, I’m going to do the grown-ass thing and critique three of Rory’s major missteps instead.

The study tree (Season 4)

When overwhelmed with her university workload, Rory struggles to find a place to study. The goldilocks of Yale can’t find a library to suit her needs, so she goes home unannounced where she throws a tantrum after finding her room in use by her mother’s business. When she eventually finds a tree on campus to study under (??), she expects the other student who’s already sitting under it to just give it up for her. In the end, she pays her way out of her problem by giving him 20 bucks to move on. 

The terrible hot take (Season 7)

In her final year of Yale, Rory attends a glitzy party thrown by her rich boyfriend Logan, where he introduces her to the editor of a buzzy online magazine. The editor invites her to submit some pieces and despite telling him she’s interested in political journalism, she writes a searing hot-take about the party complete with myopic observations about her boyfriend’s privileged friends and co-workers. When Logan reads the piece, he rightly calls Rory out on her bullshit: “Wake up Rory whether you like it or not, you're one of us. You went to prep school. You go to Yale. Your grandparents are building a whole damn astronomy building in your name.” Her response is to storm off. 

The pitch meeting (A Year in the Life)

Rory was no better in the revival. While her mistakes during college were just about excusable, her adult choices were insufferable. The pinnacle of her entitlement was her walking into a meeting with an editor with no pitch ideas. Sure, the meeting was a farce and the website and its founder were utterly ridiculous, but that’s the reality of the media industry. Jobs at the New Yorker and GQ are few and far between. When asked what the Buzzfeed-style media startup would get if they hired her, Rory’s answer is: “The person who wrote the New Yorker article”. When she, surprise surprise, doesn’t get the gig, she yells “Get Shorty!” at the editor, throws her iPhone in the bin (??) and moves back home (unannounced, again). 

In all of the above examples, Rory’s brattiness causes her to do the stupid thing. She should have just studied in the library! She should have submitted a political op-ed!! She should have spent an hour reading the Sandee Says website and writing up some pitches!!! The common denominator is Rory getting in Rory’s way. She wants to do well at university, so why is she frittering away valuable study time looking for the perfect place to study? She wants to write about politics, so why is she getting distracted by dumb hot takes of dumb socialite parties? She wants to be a staff writer, so why is she self-sabotaging an opportunity of a paycheque to write?

These are just three small examples of the many, many times Rory really just needed to suck it up. And rewatching the show has been a painful reminder that I too, don’t always know when I just need to suck it up. Because let’s be real, I’m so critical of Rory because I see flashes of myself in her behaviour. I bitch about not getting to report enough meaty features. But then I don’t make time in my schedule to pitch those ideas. Sure, the media industry is broken, but until that changes and while I choose to participate in it, I kind of do just have to suck it up. 

The great thing about working for yourself is that you can walk away from things that don’t suit you. The other side of that coin, however, is how easy it is to always chalk up a setback to a “them problem” rather than to take responsibility for the part you might have played. You can talk yourself out of ever having to suck it up.

I’m categorically not suggesting anyone endure hardship just for the sake of being stoic. And I know that I default to the defensive because, well, there are plenty of injustices happening in our working lives. But the examples I gave here about Rory aren’t situations in which she was dealing with systemic failings, bad bosses or toxic workplaces (OK, I’ll concede that Sandee Says did look pretty awful). By and large, they were all Rory problems.

And when it’s a me problem, chances are high that I probably should just buck up. After all, if what I’m doing by digging my heels in is ultimately hurting my chances of doing something that’s important to me, is it really worth it?

I take comfort in the fact that worrying about being Rory probably means I’m not her. It’s like that old joke: if you’re asking yourself if you’re a narcissist, you’re not a narcissist. This re-watching of Gilmore Girls has been instructive. It’s taught me that sometimes you do just have to get on with it because otherwise, you run the risk of ending up like Rory Gilmore – a spoiled brat who, in throwing her toys out of her pram, threw out her dreams as well.