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REBECCA JENNINGS ~ SHIT INSTAGRAM ~ 8 YRS OF VOX ~ PIVOT TO VIDEO ~ TIKTOK ~ HARDER TO MAKE MONEY, HARDER TO GO VIRAL ~
“I don't think anyone should be that tuned in to what other people are doing. But as someone who has spent a long time just observing other people, that’s what I do”.
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Friday, folks. World’s richest man is still buying Twitter, America is still collapsing into itself, and the world is burning.
But it’s the weekend.
Not too much drama on my side of the planet. We have an election coming up - your usual decision between two middle-aged white dudes who fought their way to the top through various different (but somehow the same) mazes of bureaucracy. Ah, well.
The internet, though.
Thankfully there’s more to it than what’s happening in Australia. And our guest this week, Rebecca Jennings, spends a lot of time thinking + writing about all of the rabbit holes and false-walls that make up the layers of our digital lives. That’s often depressing. But also, often, quite nice.
Rebecca and I talked about living through an entire media lifecycle while managing to stay at the same company, the rise and (potentially boring) fall of TikTok, and how there has never been more people trying to go viral and make it rich. All while it has never been harder to do so.
If you have a moment, would really appreciate you taking 60 seconds to answer our annual VFD survey. Four questions with an optional 5th. If life’s spinning too much or you can’t be bothered, I get it.
Enjoy this week’s edition of Very Fine Day.
I’ll see you online.
VFD: How you doing?
Rebecca Jennings: Good, how are you? Can you hear me?
VFD: Yeah, yeah. Can you hear me?
Rebecca Jennings: Yes,
VFD: Good, apologies, it seems like every plane in Sydney is currently descending on my house. I've been sitting here for like 10 minutes and I've had four, and I'm just like…
Rebecca Jennings: That's really funny because the sound that comes through my windows all day every day is, like, screaming children from the playground across the street. And so every time I'm on an interview, I have to explain that I'm not torturing children in my basement.
VFD: I used to live across the road from a skatepark, so I empathise with you very strongly. I imagine that you’re not getting any of those kids bringing a boombox or anything.
Rebecca Jennings: They're like little kids. They’re in, like, elementary school. And they're gone for the day because it's 4:30. But yeah, it's so loud all day.
VFD: I turned into the grumpiest, oldest version of myself living in that place. Just like, why are these kids enjoying life?
Rebecca Jennings: How dare they?
VFD: Thanks for doing this,
Rebecca Jennings: No, of course, thanks for having me.
VFD: I was reading some of your stuff this week and your piece on Instagram video. Have you got a new Instagram?
Rebecca Jennings: I think so, I don't know. It's so bad, whatever it is.
VFD: I want to die. It's so bad. And I feel like I'm the only one stuck. Like I’m part of a new culture that everyone hasn't adapted to. So you're just on the shitty version of the internet for a while.
Rebecca Jennings: I know, and it sucked before, too. But now it's like literally you cannot escape the shitty Reels and the shitty sponsored posts. And it's from people that you're like, Why am I seeing this?
It's like: Oh, yeah, because you spent two seconds on another reel because it was forced in your face. So now they’re sending you stuff like: Well, if you liked that one, maybe you like this one.
I don’t like any of it.
VFD: And all your friends who haven't adapted yet have the dimensions wrong. So you're just constantly looking at square pictures that should be wide. Anyway, this is my struggle. How long have you been at Vox?
Rebecca Jennings: So long. It’s been my only job out of college.
Rebecca Jennings: I've been there since 2014. So going on eight years.
VFD: Far out. Doing the same thing?
Rebecca Jennings: No, no, no, I've had a bajillion jobs. I was interning at this local blog my senior year of college, and the summer after that I applied for the job at our old fashion website called Racked. It was owned by Vox media, but it was more about local, retail news. So at that point my job was to go around to a bunch of sample sales — I don't know if you know what those are —
VFD: Yes, yeah.
Rebecca Jennings: Okay, yeah. So, going around to a bunch of sample sales around New York and taking pictures and blogging about it and letting our readers know if they were worth going to or not. It was awful. But then from there, I started to do more fun pop culture stuff. And then I moved over to the video team during the whole pivot to video thing…
VFD: Oh, lucky you.
Rebecca Jennings: Yeah. And then when the pivot to video thing died we were folded into Vox, and I've been writing at Vox ever since… 2018.
VFD: Right. Okay, so you've died and lived a million lives, and you’ve gone through at least one whole media lifecycle as well.
Rebecca Jennings: Sure have. And I've only been working at one company.
VFD: Stunning, does that scare you?
Rebecca Jennings: It did for a while but now I consider myself extremely lucky. Because I have amazing editors that I've worked with for so long and who just trust me to do anything. And I recognise the importance of those kinds of relationships over like, Oh, but I don't have enough by-lines on my resume. That's worth less to me than having really good relationships.
VFD: What video stuff did they have you doing?
Rebecca Jennings: So this was like 2016/2017. I went from being a writer, or a blogger or whatever, to being the writer on the video team. Because I was probably the most enthusiastic. When Facebook gave us a bunch of money to do Facebook Lives, I was like, I'll do it! I was desperate for them not to fire me. So I was like: I will do what everyone else does not want to do.
So I started by making a lot of really shitty videos, and then once we hired really good people who knew what they were doing — I didn't know how to make a video at all — we got to do some really cool, fun stuff. And I have a lot of love for that era. Like, they let me do weird comedy videos. I had a tiny little series where I was dressing like a rom-com divorcee for a week, or dressing like a Real Housewife for a week.
And if I were working at a big fashion brand that people knew about, they would not have let me do that, but because it was Racked no one gave a shit.
VFD: It's funny that you say that “era” when it was like, what, two years? Like, how long did you do that?
Rebecca Jennings: Yeah, it was 2016 through the beginning of 2018.
VFD: Yeah, it makes sense, then all the Facebook taps were turned off and everyone's learnt from it, and we're definitely not about to do it again.
Rebecca Jennings: Yep, never again!
VFD: So when you moved over to writing — well not moved over to writing but kind of went into Vox — was it immediately like Internet culture’s my thing, let’s jump in?
Rebecca Jennings: No, totally not. I had no idea what my beat should be, I felt very, adrift and like, Oh, I want to stay in video.
For a little while I was like, What if I joined the Vox video team? And I was like, Oh, they're actual professionals that know what they're doing, I am not. So I kind of just felt around in the dark for what felt good. And then when TikTok came I was very enthusiastic about it, because I could not log off. So I was like: I think this is going to become a big thing because I personally am addicted to it. I was pretty early on that, and so they were like: Okay, write about it then.
I wrote a couple of stories, and from then on, I just was like, This is my beat: internet culture + TikTok + what’s going on.
VFD: Why do you think TikTok has that kind of longevity?
Rebecca Jennings: I mean, it was hard at first because it really did seem this is just a fad. People were really quick to be like, Oh, that's cringy, it's embarrassing. It was like a liability to be on there for the first couple of months.
VFD: I’d say years.
Rebecca Jennings: Yeah, it really wasn't until the pandemic where people started taking TikTok at all seriously, for sure. So in the first year or so, the reason I was on there was because it was cringy and I enjoyed the schadenfreude of looking at all these, like, losers who didn't know how embarrassing they were being. I know it's horrible, I know.
VFD: No, I get it. I totally get it.
Rebecca Jennings: But once you spend enough time there it shows you these hilarious people that are just random people that would have been the funniest kid in your grade growing up or something.
And you just got to know them over time. You saw these really, really hysterical videos in a way that was easier to navigate than I think Vine ever was. And I think because people were so like, Oh, it'll never replace Vine. We're still so obsessed with Vine, they really underestimated it. And also because it's a Chinese company.
So people are like, Oh, this is like a blip, this is nothing. And so it was easy, or it was kind of nice for me. I didn't really have a beat, I was like, Okay, this isn't a very competitive beat. It's not like I'm jumping into the world of politics or fashion or something where people are really, really established. I was sort of like, Okay, I'm a little baby journalist, I’ll make this my little corner and then it becomes like this huge news story.
VFD: Yeah, it's pretty wild. I think about how in 2019, when I was on TikTok, there were so many very insular, small subcultures. That were — as you said — by and large, quite cringe. And often when I'm on it now I'm like, Do they still exist? And they still exist, obviously — but I mean, are they still on this app, and I just can't find them? Or was there some awful kind of transition that included a feeling of you stole this place from us? The mainstream stole this place!
Rebecca Jennings: I think there's definitely a sentiment on the platform and elsewhere on the internet that TikTok is boring now. And I sort of feel a little bit exhausted by it a lot of the time. Especially just writing about it and reading other people write about it. And it's just like, This is not interesting. Like, for a while, especially during the early pandemic, there were all these stories that were just like, This is something that's happening on TikTok. I'm like, Yeah, it's also happening, like… everywhere else on the internet. And it's also one of the 1000 things that are going viral right now on TikTok, and you just are picking out the one that you want to write about, or you find interesting. Which is fine, but don't pretend like this is the entire app.
Anyway, as it's gotten more mainstream it's also more competitive to go viral on there. And it’s also more difficult to go viral on there. So you don't get as many huge shoot-to-immediate-success stories as you did in the first two years of it existing. Which, you know, for some people, it makes it less fun. For others, it makes it a little bit more stable.
VFD: I mean, I think there's no shortage of people trying. Just because it's gotten a lot harder, I think it's remarkable how many people are just really, really strapping in now in the last six months.
Rebecca Jennings: I know. And it’s even though we know, as a culture, how shitty it is to be famous. And yet people will never tire of trying. It's fascinating to me.
VFD: It's right there. It’s one video, right? If I can just make the perfect viral video, then I'll get a sponsorship, and I'll be rich.
I do try not to think too much about it. I have young nephews and stuff — and I'm like, This is not good for you.
Where did you go to school? Did you do media? Did you do journalism?
Rebecca Jennings: No, I did Media Studies and Creative Writing at NYU.
Rebecca Jennings: Because I remember when I was in my early teens, I was at some family party, and my uncle had this friend who was a journalist at Time Magazine. And the one piece of advice that he gave me was: Well, if you want to be a journalist, do not major in journalism. So I didn't major in journalism.
VFD: That's really good advice that not many people get.
Rebecca Jennings: I know right.
VFD: And then how did you transition. Was it always like, I want to be a journalist?
Rebecca Jennings: It was always like, I want to be a writer. And journalism seemed like a way to get a job doing that.
I started creative writing, that was my passion. But I also did journalism in high school and in college. I basically had this idea of working in media because when I was in college, I dated a guy who was working in this new era of digital journalism, or digital media. And I was like, Oh, my God, that looks so cool and fun and glamorous, I wanna do that. And I remember telling one of my professors: I just want to be in media. And they're like, Well, what do you mean…???
VFD: So you're looking at free snacks and blue checks on Twitter and you’re like: That’s me all over?
Rebecca Jennings: Well, I used to go out to happy hours with him and his co-workers. He was several years older than me, and I was just like, These people are so cool and so smart, and I just felt so stupid and dumb next to them. And yeah, I was like, Maybe someday when I'm older, I'll be cool like them.
VFD: You did it. Do you feel like you did it? Are you like: This is what I meant.
Rebecca Jennings: I don't know. It's obviously that once you're in something versus you seeing it from the outside as a younger person, I definitely have this chip on my shoulder. I was like: I'm never gonna be good enough. It's like: Oh, my god, get over yourself.
VFD: Yeah, I don't think that's unnatural for anyone doing anything in the creative field. But particularly in media, because there's not much built around us to make us not feel that way. It’s actually built to make you feel that way. Which is cool. And very healthy.
I read somewhere that you said — Where did I read it? I can't remember — But you said you “weren't like an internet kid”. And I was like: how does that translate to writing a lot about the internet? Or is the secret to it that you have to hate what you inspect?
Rebecca Jennings: Well, I think that's why I'm so interested in it. Because yeah, my time spent on the computer at home was AIM, it was a little bit of chat rooms. But those were activities to do with friends I knew in real life, it wasn't using the internet as a place to escape to. And I didn't know that there were places that you could go if you wanted to, like, talk about Harry Potter with someone. I was a big Harry Potter kid, and I'm kind of sad that I didn't have that, but also grateful at the same time that I wasn't exposed to Tumblr when I was in my teen years.
I think growing up the way I did, I would always see people that were living in big cities and who seemed to be very tuned into pop culture and what was cool. I would always look at those people and be like, Whoa, they're just living on a different planet.
And I always felt like I wasn’t living on the same plane as people that went to schools where people wore designer clothes, or where everybody had these things that I would read about in magazines. I was fascinated by it.
VFD: And then was there a moment that you got it?
Rebecca Jennings: I think that I'm still trying to get it. Because now obviously I write about culture, and I know about things before most of my friends who do not work in a culture industry do. But I think that makes me probably a worse person than them in a lot of ways.
Rebecca Jennings: I don't think anyone should be that tuned in to what other people are doing. But as someone who has spent a long time just observing other people, that’s what I do.
VFD: So you don’t get tired of being online?
Rebecca Jennings: Yeah I do, and I'm actually really good at logging off.
VFD: Oh, really?
Rebecca Jennings: Yeah, oh my gosh. I know that there are people that cannot log off and are addicted to any kind of new thing, but I really relish putting my phone on Do Not Disturb. I'm not addicted to TikTok at all. I think that when there are moments where I can feel myself doom scrolling, which happened obviously last week with the abortion stuff. I can feel it happening and I'm like, This is bad. This is bad. This is bad.
Rebecca Jennings: I was like, am I gonna get fired? Do I care? I was just so upset and my boyfriend had to come in and be like, Log off Twitter right now. This was hours later after I tweeted that. You could tell that I was still scrolling.
VFD: What is America like right now?
Rebecca Jennings: It's funny because my view is probably similar to yours. I see most of the discussions happening on Twitter, really, or on Instagram or on social media. Obviously I talk about it with my friends, but the majority of my interaction with politics is via the internet. So it's not much different from anybody else's.
VFD: That's interesting. Is that something you're comfortable with?
Rebecca Jennings: I don’t know. I never wanted to be a politics reporter or a current events reporter or a scoop journalist. I'm not a news junkie in any regard.
VFD: But you do get scoops. Like, I'll just see the headline that you put out and I'll be like, Fuck, that is good. Like, Yeah, that is happening.
How do you understand that it's worth a story - this thing that you've noticed.
Rebecca Jennings: If it's something that's both new/novel, but also something that has been trickling in. I think it could also be that there's one weird trend, or whatever that is, that comes out of nowhere. A
And you know, people who are in my life who are less online, if they're talking about it. That's when I know it's something worth explaining and worth writing about. I don't typically try to be first to a story. I try to be someone who can speak to people who don't spend as much time online as I do.
VFD: Do you find you have the same conversation with some of the people you interview. YouTubers, and TikTokers, and anyone who makes a living or has a living online. Because that's one thing I've ever encountered in my career: Oh, we're doing this again? Oh, yeah. Yep. Yep. I know where you're heading. Yep. Okay, cool. Like, I have this database of being able to see where the road is heading.
Rebecca Jennings: I know. Oh, my God, truly. Every famous TikTok person is the exact same way. They typically come from complicated family situations, and then they blow up on TikTok for XYZ reason, and now they're shunted into this world. And there's only so much of that kind of story to tell that we have told a jillion times.
VFD: I get kind of caught up in the moral responsibility of telling people, internet people, internet famous people: I know it's not my responsibility. And I know you don't care. But I hope you have a backup plan. I hope this is not your whole thing. I also find it interesting that it's — particularly with TikTok, and it makes sense — so often kids from like, Missouri. And they’re like, I don't do anything, I stay at home, I make a TikTok. And that's when I hear alarm bells.
Rebecca Jennings: And it's so hard to talk about without sounding very prudish and —
Rebecca Jennings: Old, and someone who just wants to create these concern troll-y, moments.
VFD: Hey, thanks again for doing this, Rebecca.
Rebecca Jennings: Yeah, thank you so much. Can't wait to read.