Lily Herman: An Interview with a Journalist Extraordinaire

Lily Herman ’16 in front of Usdan. Sorry we used this old ass photo of you <3 <3 <3 (Photo by Olivia Drake)

This year, Lily Herman ’16, is teaching a class in the Center for the Study of Public Life called “It’s a Mess”: An Academic and Practical Look at Digital Media in the Late 2010s. She is a contributing writer at Refinery 29, where she writes about news and politics. She’s been featured in a host of other major publications such as Allure, Teen Vogue, and ELLE, and is the founder of the digital media company Rogue Sunday.

Lily’s pretty busy right now between teaching and covering midterms (!GO VOTE THIS TUESDAY NOV 6!), but I was able to catch up with her for a bit. The interview is after the jump:

You majored in sociology and government when you were here. How did you go from that to where you are now, in a career in Journalism? Following that, how did Wesleyan influence your career choice?

Yeah, it was all happening I think simultaneously at the same time. I arrived on campus as a freshman, I came to Wesleyan wanting to do politics – I wanted to be president – I showed up and ran for the WSA, got on it, and was there for two years. But realized pretty quickly, within a matter of weeks that that was just not necessarily the career path I wanted for a variety of reasons, and started writing for Wesleying my first semester and really liked it, so I just sort of pursued it. And then, while all of that was going on, I was obviously trying to figure out what I was going to major in. I knew government was going to be one of the two things off the bat, and being sort of over-achieving I was like I’m going to double major. I actually walked into an intro soc class my second semester and immediately loved the professor. He was visiting for only that year – I think Matt Williams. He was phenomenal. A lot of what I was learning in classes instantly applied to a lot of what I was doing in terms of the other work. In terms of the writing, social media, PR stuff I was doing throughout college, all sort of connected by understanding the larger institutions and systems that were governing whatever I was up to. They informed each other. It was fascinating being in the world of Wesleyan academia and college student stuff and simultaneously being a writer and having these very adult professional responsibilities that went far outside of campus.

I think Wesleyan influenced my career choice not in an upfront way like you might suspect, and not in the way that we tell students that you should suspect in terms of, “you go to school, you choose a major, you do that to launch your career”. I think Wesleyan influenced my career in terms of the people who went here. I think a lot of the thought and the really radical ideals that exist here were really good to be exposed to early on, because I found in my career that lots of people don’t get that exposure until well after college if you’re lucky and then they have to do a lot of self-discovery on their own, whereas I kind of skipped that and got to be around people that were always saying and doing interesting stuff. I think that’s where Wesleyan had the most influence, in terms of getting to do what I wanted and no one really questioned anything I did. I didn’t really have to deal with any obstacles on that front which was really, really great. It’s not like I walked into a classroom and said to a professor “This is the career path I want!”

How did Wesleyan prepare you for the real world? In what ways did it not? Relatedly, what are some life lessons you’ve learned since graduating from Wes?

One of the best events I ever went to was in the first half of college we used to have this thing called “Wes Thinks Big”, it was kind of like Ted talk style where different professors would come up and talk for ten minutes. And there was a professor, Elvin Lim, he was a beloved government professor at the time, and he did this great talk whose thesis was basically, “question anything that is anything/idea/institution that seems normal.” Which isn’t particularly radical now that I’m older but as an eighteen-year-old I fixated on this whole concept. So I think the best thing out of Wesleyan was this sort of idea of questioning what’s around you and never taking no for an answer.

I think the big obstacle that pretty much any liberal arts college is facing is learning for learning’s sake is great, but also we’re living in a time when kids are coming out of school with six figures of debt and lots of other issues and the real world is a big scary terrible place. Or so it seems. There’s always this sort of push and pull over how much of this world should resemble a utopia, and how much should resemble what you’d see in real life. I think that’s something different for everyone coming out of college. But I think liberal arts schools like Wesleyan are facing that harsh reality of what’s actually out there.

Wesleyan-specific: not having a landlord for four years was phenomenal. I have a truly satanic landlord currently. Wesleyan didn’t prepare me for how to deal with a terrible landlord that doesn’t fix anything in the apartment. Physical plant is wonderful and if anything comes out of this article it’s that students should treat physical plant better. That’s my two cents.

You’ve written a few articles about how you first got your work into Teen Vogue and Medium; could you expand on that? How did you get your foot in the door post-grad?

I think in terms of my political writing career it’s sort of fascinating, I, through a series of bizarre circumstances, got a “tech writing job” at Teen Vogue my senior spring and the second I signed on I never just did tech. I did pretty much every vertical except fashion and beauty for them. So what was fascinating was, that started in March of 2016, I graduated in May, Donald Trump was elected six months later, but by the time Donald Trump was elected, I’d spent six months doing a huge portion of their news and politics coverage in addition to their tech writing, food writing, décor and lifestyle writing, just kind of anything they needed. So the nice thing was that was the latest foot-in-the-door when I was ending Wesleyan, and it was also the foot-in-the-door to political writing, where Lauren Duca had this op-ed go viral in December 2016 called “Donald Trump is Gaslighting America”and then everyone was suddenly paying attention to Teen Vogue’s political coverage. At the time, Lauren Duca was the weekend editor, and I was writing anything from 40 to 70 percent of their daily news and politics content. So that sort of snowballed into a bunch of other things – I was friendly with a variety of editors and writers online and elsewhere, and I’d never written a political op-ed when I was getting drinks with Glamour’s news and culture editor and she was like, “My op-ed writer for politics is on maternity leave, you write those right?” And I was like “Yeahhh…. I do write those… I love those!” I got the Teen Vogue job submitting clips I had from another job I’d had writing for two years in college, so there’s no real specific thing necessarily, it’s just been this sort of strange snowballing of I worked really hard at a lot of stuff and these pieces I have no control over, like who gets elected president, or Lauren Duca’s op-ed going viral, and people caring about Teen Vogue. All that stuff happened after-the-fact.

What’s it like to contribute regularly to such big names in media? What are the differences you’ve found in writing for the publications you do?

It’s cool, I have my pinch-me moments every once in a while, but a lot of the time it’s just writing. Like when I’m writing my articles, then editing them, then taking my editor’s edits, and trying to do all that in the span of a matter of hours for an op-ed or something, it’s overwrought with a lot of stuff going on, but overall definitely cool. Especially because I was a Teen Vogue subscriber as a teen, it was very nice to be a contributor there. The biggest difference in the two I’d say is their audiences. They have a pretty similar voice in some respects. They also, especially from an opinion writing perspective, let me do whatever I want. At Teen Vogue though, I wouldn’t pitch an 80 year old subject unless there was a really good reason, because they kind of stoop younger. Whereas Refinery would probably pick up a pitch that Teen Vogue would not.

How have you navigated an industry that is predominantly white and male?

Up until December of this year, when I was working on a single project, I had never had a male boss ever – and that includes all the other internships and jobs I had in college. And part of that was just because I was a freshman with no writing clips. But then, after a certain point, it kind of became a conscious choice to only work for women. So that sort of worked itself out, in that I’ve gotten to avoid a lot of the internal politics of working with men until this point. But then similarly yeah, because I do other work in marketing and PR, when we’re pitching out articles I do have to deal with more dudes than I ever did up until this point. There’s definitely differences in the little frustrations I see, in terms of how that works or how men are allowed to act in workplaces versus women, which is really fascinating. A lot of it has  just been avoiding it, by only working for women who I believe in a lot.

We’ve been talking about the potential downfall of print journalism in class. Where do you see journalism going in the future?

I think it’s sort of the idea that we just have to shift what form journalism comes in. I mean print is not the form anymore for a variety of reasons. I don’t necessarily want to be like, “It’s dead! Forever!” But I think it’s not going to be the dominant form from now on – at least until all of our computers crash. I think right now journalism is contending with how many forms it can come in, and whether or not you can pay for it. At the end of the day, unfortunately, journalism’s going to go where the money goes, and right now no one seems to have a good answer to Who pays for journalism? Like actual hard hitting, reported, fact-based journalism.

How did you get the idea for your digital strategy firm, Rogue Sunday? How did you put that idea into action?

When I was at Wesleyan I did a lot of random freelance work in terms of marketing, social media, PR, and copywriting on top of that I was writing for other websites. I had one internship where I was a communication intern, and when I quit really abruptly they were like, “Hey can you do our social while we’re looking for a new person?” So I was like “Okay” – I was like 20 – and over time I built up this separate other side set of skills. About a year and a half ago, it got to the point where, on top of everything else, I had a couple other projects and I was starting to get more offers to do work, and you can only scale so much as one person, so I had to say to myself, “You can either start turning down opportunities or hire some people to help me do this.” So it grew from a really organic place, getting the legal backing for something that was kind of already existing. So, Rogue Sunday has existed as an entity since January, but my career in that space has been there for 6 plus years at this point. We’re a generalist marketing strategy firm which is really fun, so we get a lot of different types of projects, and all of our clients are in some way making the world a better place. I always joke with everyone saying we have a “no assholes policy” in terms of our clients and our team members, which is really great, and similarly our whole team right now is entirely women and non-binary people, and predominantly women of color. We’ve got a great team – everyone’s really nice to each other, and it’s been fun to build out! Even when it’s stressful, it’s made easier by the fact that we have nice clients and really interesting work to do and a lot going on all the time.

What was it like writing about politics during the 2016 election? What specifics did you cover, and how did you target all of it towards Teen Vogue’s audience?

It was, at the time, a little bit stressful and also odd. Pre-election it was kind of a bizarre universe where you’re like, “this must be an alternate reality: there’s Hillary Clinton running one sort of campaign and Donald Trump running a totally different one.” Post-election it was definitely surreal, just trying to figure out how to cover a President who lies all the time and is just a pretty terrible human being. All journalistic outlets have been trying to figure out how to do that in a way that is ethical but also makes sense. It was fun in a not-fun way, because it’s empowering to give people news that you feel that they should and need to read, but it’s also tiring, and this news cycle never quite ends. It was also really great to know that there’s a mix of young people who read my work. There’s also parents who have subscriptions for their kids and they also read the site, so hearing from parents or grandparents who read Teen Vogue is also very rewarding.

How did you get the job at Refinery following Teen Vogue?

I’d actually freelanced for Refinery before – I submitted one-off pieces to them. I had a friend who was doing some editorial consulting there, and she saw a snarky tweet I wrote and asked me to do a longer piece about it, and I wrote one or two other things after that. Interestingly, a couple months after I’d written these pieces I was reached out to by their executive editor, because at the time they wanted someone to cover what was going on with healthcare and get some takes on that, which I did, and then a month after that I had a meeting with them, sat down, and they offered me the contributing editor job which I was very, very interested in. Pretty much the breakdown of it at this point is Refinery has my political op-eds. They also have something called first-pitches rights to my work in terms of political writing, which basically means if I have any ideas for articles I have to run it by them first to see if they want to take it. The good news is that at this point I know what they do versus what Teen Vogue does and where that overlap doesn’t exist. The fun thing about that is having a place that kind of houses everything I do and a place I can go to with ideas, but if they’re not interested its not the end of the world, there are plenty of other places I can take things to.

What kind of pieces are you working on now?

For Refinery I’m trying to plot out what my pre- and post- midterms and op-eds are going to be, what sort of pitches make sense right now – there are a couple other pitches in the works that I had sent to my editor and need to refine them a little bit. I was sick for a month and a half over the summer so I have a list of things. There’s a lot of organizations that contacted me over the summer about the young people running this sort of organization. A lot of young people are running for office right now who want to be profiled, and that’s a huge thing I’m trying to knock off my list because I also love doing those profiles. Teen Vogue has me helping out with a political candidate project they’re working on for the midterms. I also then have a whole other list of pitches and ideas that I just need to start submitting to people that aren’t politically related that are wellness related or career-related or things like that. There’s always a list of like 20 things that are in the works.

What do you do to get inspiration and what do you do to get over writer’s block?

When I need inspiration it’s always a combination of things: first of all getting off my computer and walking around, just in general, to let your body work through whatever it needs to work through, also just going out and talking to people – it doesn’t have to be other journalists or sources – but people always kind of just know things. I’ve had a lot of stories where I was talking to someone about something super random and then they sort hit some nerve and I felt like I knew what I was going to write about. In terms of writer’s block, studies have proven that the best way to get over writer’s block is just to write something, which I would agree with. So, even if it’s something small, I’d block out all of my sections for an article or what my major points are and then work through the sections that are the easiest and work through there. Even if it’s complete crap I’m writing, it’s just nice to have something, from a psychological standpoint, on a page so that I’m not staring at just a blank document. I think the nice thing about having written so much in college is that I didn’t really have time to sit there and waffle over an article for five weeks, I just sort of had to figure it out and write it and if I turned in some crap I turned in some crap and had to move on from it. So at this point, there are days where I’m like “I have an hour and a half to write an op-ed” and I’ll write for 45 minutes, reevaluate, and pivot if I need to.

What are your goals? Where would you like to be in five years? Ten years?

I have no idea. I’m someone who kind of will have general things I want to accomplish and set out to do, but I’ve just found that I’m not one to do any sort of planning. I couldn’t imagine where I was a year ago, let alone where I’ll be at 34. Who even knows where I’ll be at 25, let alone anything other than that. Honestly, yeah, I don’t really plan much for the future which I think surprises people. I sort of take whatever opportunities sound interesting and are different and if I feel good about them I do them and if I don’t, I don’t. I still say “yes” to way too many things than I should, but it’s been a good strategy that has not failed me thus far. It’s also just led to a lot of flexibility to not have a career goal or dream job, especially since in media the industry changes every five seconds. So that’s really helped because I don’t know how it led me here, but it led me here.

What’s your favorite Wesleying piece?

My senior year, me and the writer Wilk got to go to these two friends in my class year’s pop up restaurant they opened in their house called “Red Wolf.” We got like a free three of four course meal and wrote this fun review about it and it was really great. That’s the one that I think sticks out, especially because it’s hard to remember the rest of them because there were so many.

Falafel or Whey?

Whey. I’m a cheese fan. I tweet all the time about how I have treat-yourself cheese Saturdays, and so my love of cheese, specifically gourmet cheeses, is definitely well-known. Falafel is delicious – I’m totally not saying that it sucks –  falafel’s great, but if someone was like, “You have to choose for the rest of your life,” I would choose Whey. Because I just need cheese, more than I need falafel, like as an actual food group.


This interview has been edited and condensed for clarity.

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