I recently came across this brilliant CNBC article by Ester Bloom that talks about Rory Gilmore’s freelance journalism career in the new reboot and the many terrible rookie mistakes she makes.


I thought I would compare, side by side my own writing venture with Rory’s big no-no’s to see how much of a rookie I am as well, or to just see if maybe her mistakes make sense in the grand scheme of things.


But first, let’s get the basics out of the way.



Rory: Yale Educated, degree in journalism.


Kay: Not Yale-educated, not even close, degree in English and music.


Rory: Jet-setting, freelance journalist.


Kay: Returned home with no prospects (except my home is not filled with delightful wacky cohorts).


Rory: Internationally recognized, award-winning journalism prodigy with clips in the New Yorker and The Atlantic.


Kay: Submitted two pitches to the Atlantic, both of which were never heard from again. Barely locally recognized, freelance writer, with clips in Strangerthings.com and Travel101.com.


Rory: Rich!


Kay: Will be paying student loans until she dies.


And with that, let’s get into the mistakes that Ester Bloom talks about in the article. Just to be clear, the quotes are directly from the CNBC article.



1. “She’s a freelancer without an anchor client”



According to the article, an anchor client is a necessity before starting out. A reliable source of income that helps pay the bills while you pitch articles and work on your novel. The idea is self-explanatory, and a really nice idea.


Don’t start freelancing until you have know you have the gigs and money to back it up.


I was totally guilty of this, like Rory I was going from article to article hoping that would lead to bigger projects. In my case it did and now, after 6 months I have my anchor client. So that’s 1 for 1 on the list of biggie mistakes.



2. “She spends unearthly amounts of time and money flying across the Atlantic ineptly putting together a book proposal about an absent-minded alcoholic.”


No, this is something I can’t relate to. I did, however, spend unearthly amounts of time watching Netflix and Hulu.



3. “She calls an editor to pitch a story”



I have only ever used email. I use emails to “cold call” potential clients, it’s how basically every editor, website, and publication wants you to query articles, and it’s my main communication for freelance writing.


That said, when I read, Writer for Hire by Kelly James-Enger, she talked about actually cold calling.


She writes, “you have to be able to sell… and selling includes making cold calls”


Enger is actually talking about cold calls, as in picking up the phone, going through contact numbers and so on. She explains her process of contacting 5 or so possible leads each week.


Now, in 2017, I would argue that actual phone conversations are a thing of the past in terms of cold calling.


But Rory’s call to pitch a story might just be because that’s how the writer, Amy Sherman-Paladino, remembers getting business done and possible writing leads back in the day.


So, I’m calling this not a mistake and just a little dated.


4. “She agrees to work for free for that editor, even though she’s broke and not actually excited about the story”



Yep, I’m guilty of this one. Especially when I’m writing about something I’m super passionate about like film reviews. I think that writing for free has its value, and at the point when Rory does end up taking the story, it’s an act of desperation.


So that’s 3 (not counting the cold calling) for Rory and 2 for Kay.


5. “She shows up to a job interview with Sandee of the up-and-coming website SandeeSays embarrassingly unprepared.”




6. “When Sandee asks Rory to come up with some pitches for the articles she would write for the site, Rory can’t.”


(I’m lumping these together)


It wasn’t until I was interviewing a source for another article I was writing that I realized the importance of pitching to clients. I, probably like Rory, would just send out a letter of introduction and hope the for the best.


In this case, Rory went to an interview for a content position with no content ideas and very little info on the website. Clearly, her heart wasn’t in it, but it’s an understandable mistake. You think your portfolio should do most of the talking.


Now, whenever I’m pitching potential clients I try and have at least 4 or 5 blog posts or article titles at the ready to pitch. That way, I introduce myself, show my writing know how, and prove that I can be an asset to the team, taking initiative and coming up with ideas. Although it’s way easier said than done.


Rory: 4, Kay 3


7. “When Sandee calls Rory after the interview, Rory throws a tantrum.”



Rory was told she wasn’t a good fit, and truthfully, she wasn’t. And instead of accepting the rejection she was vocally upset.


One of the worst rejections I got was an email that told me I was very much in the running but was just narrowly edged out by someone better. Now, on the other end of the computer, I was pretty upset about that.


To be told that I was so close but yet not good enough, well that was a bummer. And certainly a little bit of oversharing on the case of the client. But I responded with a hearty thank you and asked if I could potentially reach out in the future.


Rejection stings, and sometimes it’s not fair the amount of hoops and work you have to do just to have the door shut in your face. But rejection is part of the business and how you handle it matters.


The Final Score

Rory: 5

Kay: 3


Now, while comparing myself to a fictional character might seem like a futile task, like Bloom’s article, sometimes it can be interesting to see where you measure up.

Of course, spending an episode of the new Gilmore Girls where Rory writes cold emails, researches potential clients, comes up with pitches, and boosts her social media presence would be just plain boring.

But having Rory falling asleep while interviewing a source and yell at her boss, well that’s entertainment.


How many of these big “No-No’s” have you been guilty of, how do you rate with Rory as a freelancer?