Journalist Rebecca Jennings on leaning into what only you can do

Your work has become must-reads for anyone interested in the horrors and fascinations of internet culture and you always seem to be three steps ahead of the curve. How are you able to report on trends before they even pop up on anyone else’s radar?

That’s so funny because I don’t break news, ever. I am not a scoop reporter. I write the “day three” kinds of stories where someone breaks news, there’s a couple of hot takes, then I’ll try to write a more thoughtful explainer and contextualize whatever news item is happening. To me, I’m not even first to a lot of things and I’m okay with that. I try to take something that’s really bubbled up in the mainstream culture, something people might be confused about and explain it. I don’t think of myself as someone who is really early to trends, it just happens to be that I cover a subject people tend to think of as the “what’s next.” People are very scared of technology and culture. When you spend so much time online it’s kind of impossible not to see patterns everywhere. These things have a very predictable way of playing out, honestly. I find myself a lot of the time writing the same story over and over again, which gets a little bit frustrating.

Is there a certain quality you pick up on that makes you want to write about a particular subject?

Because so much of internet culture is just repeating stuff that happened five years ago, 10 years ago, or 20 years ago, I look for something that is actually novel or worth explaining. The latest dustup, West Elm Caleb… It happens so much over and over again at a certain point it’s not interesting because we’ve done this so many times before. A lot of the time, a dance or a trend on TikTok does not warrant any coverage in the press at all. It doesn’t say anything about society, it’s just a thing that happened to go viral… I think something that hasn’t already happened a bajillion times online is worth covering.

That reminds me of the piece you wrote on garbage internet trends. Why are we as a culture so drawn to trying to parse out the meaning of meaningless stuff?

In a way that I didn’t see years and years ago, people have really seized on new novel concepts as a way to try and predict the future. There are so many fads and crazes that happen now because of apps like TikTok that move very quickly. I think people are clinging onto something that might help them understand what might happen next because the world is so unpredictable. The economy, culture in general, politics..those things are impossible to predict right now. To me, the real fervor behind being the first one to name a trend, or jumping on some dumb crypto scam, is just a reflection on the fact that people are scared and confused.

What creative process do you go through before sitting down to write? Are you constantly combing the internet for story ideas?

It’s funny, I spend so much less time on TikTok than I used to - partly because it’s just really exhausting. My For You page is filled with teenage girls talking about whether sex work is feminist or not. That’s just not something you’re going to have a productive conversation about in the format. I think, “Oh my gosh, none of you have been sex workers, none of you know any sex workers.” To act as if you know everything in a three minute video is really frustrating. But usually I’ll be on Twitter, TikTok, or Instagram and if I see something interesting I’ll write it down then try to see if it comes up again. Once I have noticed a couple of trends that fall into the same category, I will think of an angle that isn’t immediately reactive, and then I’ll reach out to the creators that have been involved and see what they have to say to determine if it’s worth talking about. Sometimes I’ll follow a lead into a story and there’s just not enough there. But sometimes I’ll talk to those people and find an in for another really cool story that’s happening. Like every reporter, I have a giant list of things I am interested in and add to it as the weeks go on.

What is your personal relationship to the internet like? Have you always been extremely online?

I was not an internet child. I was a Microsoft World child. I wrote a lot of fanfic when I was a kid but I never put it out there because I didn’t even know there was a place for it. I cared about the internet because it let me post on MySpace or my AIM Buddy profile or later, my Facebook. I just liked sharing pictures with friends. I wasn’t one of those internet children who I report on now, which is why I think I’m so interested in it as an adult. I wasn’t even really a pop culture kid. I didn’t have cable growing up in Vermont. I was constantly doing other things. I wasn’t consuming stuff. So being introduced to the wider world of celebrity and internet culture as an adult has been really fascinating.

What do you mean you were a Microsoft Word kid?

I wrote stories constantly. Fiction, short stories. Me and my friend would write CSI fanfic back and forth to each other and we would insert ourselves into the plot. It was very racy. We were like, 12. I was married to Greg, she was married to Nick and we were both sleeping with each other’s husbands.

Are there any habits you’ve picked up that you find particularly useful when it comes to your writing practice?

One thing I do that I’m very proud of is I spend my TikTok hours on the treadmill. I walk uphill—it’s actually an exercise routine I found on TikTok—for 30 minutes at 3 miles per hour, with the incline to 12. It’s a pretty good workout, but you’re not running, so you can easily scroll through TikTok. I feel like one of those horrible hustle culture gurus who is like, “Only watch TikTok when you’re working out.” Other than that, not really. I have a newsletter I write once a week for Vox so that’s a cadence that I have to subscribe to at all times. But I’m a very chaotic person in general. I’m not exactly a Type A personality. I’m a “throw everything in a Google Doc and figure it out”-type person.

Do you keep 9-5 hours?

Because I have a salaried job, I have to be online at 9:30 and I typically work during normal work hours. I’m not going to say I work until 6 every day because that’s a lie. Sometimes I’ll do a workout in the middle of the day or go on a walk.

You’ve been at Vox for over six years which is a really long time in this industry. Tell me a little bit more about your career trajectory.

I’ve been at Vox my entire career! For a while I was like, “What am I doing, why am I still at the same company?” But I feel like I have a really good situation right now. I went to NYU and did unpaid internships at a couple places, Time Out New York Kids, this really shady travel website and this place called The L Magazine, which no longer exists. I was writing about bloggy New York-related stuff. This was 2014, so it was a very hipster era where people were writing cool snarky blog posts. I was obsessed with The Awl, Gawker and Thought Catalog at the time. I loved it so much, I just wanted to write shit on the internet.

I was there the summer after I graduated. Then Racked New York had an opening for an associate editor and I got it. The whole job was essentially blogging and walking around to New York City sample sales and writing reports on them. It was me carrying around my super heavy laptop at all times. I was making no money, I was very lonely.

I did that for like a year then I moved over to Racked national and wrote blog posts about whatever Kate Middleton wore when she left the palace. It was mostly finding funny headlines to put on her outfit photos because those posts would get a million clicks. They were pretty much the only thing that would get a lot of clicks on Racked.

Then the whole “pivot to video” thing happened in 2016 and I moved over to the video team. I was the main editorial person on the video team, so I wrote a lot of scripts and appeared in a lot of videos. Then the “pivot to video” thing ended and Racked was shut down in 2018. They kept 10 of us to start a new vertical on Vox called The Goods. I kind of got to pick what I covered. I didn’t really have a beat before that so I was kind of feeling around in the dark until TikTok blew up and I realized I was interested in covering this new creator industry.

Do you have any qualities that make you uniquely suited to the kind of work you do?

I write a lot about young people and I’ve worked with kids my whole life. That’s something I’m pretty natural with. I coached figure skating for a long time and babysat. I have a really easy time talking to sources. A lot of my interviews are like therapy sessions, it feels like. I really enjoy that part of the work.

What kind of advice would you give to someone interested in pursuing a similar career path?

It’s more difficult to get a journalism job now than it was when I started out. But at the same time there were so many shitty, exploitative jobs back then and a lot of them are gone because those companies don’t exist anymore or they have been replaced because the companies have unions to protect workers. The jobs that do still exist are better jobs, but it does make it a little bit harder when you’re starting out. I think, especially for young people, lean into what you have that nobody else does. I tell student journalists all the time that they have access to sources that most adult journalists do not. They are already in the spaces where kids talk and hang out and most of the time, adults aren’t part of that world. If you want to be a journalist, just pitch everybody. I send people who ask for career stuff this really good pitch guideline Medium post by Ann Friedman. Join a collective like Study Hall to get a handle on the business of freelancing.

This content originally appeared on The Creative Independent and was authored by Isabel Slone.