Deez Interviews: Meet the tireless news & entertainment writer who’s trading in the New York media scene for Maine
Happy Friday, Deezers! For all of our new friends, Fridays are when we publish a Q&A with cool people doing cool things in the media industry (a few recent faves were with Longform’s Max Linsky, The Atlantic’s Taylor Lorenz, and GQ’s Stephanie Talmadge).
Today’s interview is with Hilary Weaver, who, after a tour of some of New York media’s biggest titles, is now heading out for a new adventure in Maine. If you know Hilary, this news is basically like finding out that the Chrysler Building is picking up and shipping out, but we caught up with her before the move to talk about how celebs are kind of like snakes (but not in THAT way) and how being “midwestern nice” lowkey pays off. Enjoy!
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The interviewee: Hilary Weaver (follow her @Hilary_Weaver)
The gig: Formerly weekend editor at ELLE, newly the digital editor at the Bangor Daily News
Across your work at titles like Vanity Fair, ELLE, New York magazine, and Bustle, you’ve mastered of staying on top of the 24/7 news cycle and working with SUPER fast turnaround times. How did you get so good at that?
When I first started out, I was definitely not used to the fast turnaround. I went to a pretty traditional journalism school and most often worked at a print magazine pace, where I had at least a couple of days to turn something around. I learned quickly that writing as a professional these days means blogging, and blogging deadlines are about minutes, not days.
Once I understood that, I liked the rush of getting an assignment and then having it off my plate within 20 minutes. This pace was stressful at first, but once I get the hang of the technical stuff (finding a photo, posting a snappy headline), it became a sort of a meditative process.
Just like most tasks in my life, I tend to get tripped up on the little things, like embedding a video; the writing itself is not the hard part. Once I felt confident in every other part of the publishing process, my writing got stronger, faster, and, frankly, funnier.
You just wrapped up a stint as the weekend editor at ELLE now, and before that, you spent time as a night editor for The Cut a few years back. I'm so curious about the ways you organize your time when you're not on the schedule that everyone else is on!
I was at ELLE from February through mid-May of this year. Getting back into an abnormal schedule after nearly three years of full-time staff work wasn’t as hard as I thought it might be, because before I got my first staff job at VF, I was used to random hours.
At The Cut, I used to work from 7 p.m. to about 2 a.m. and freelance and nanny the rest of the time. I learned early in my career that I had to make my own free time. I am often tempted to take on an extra freelance project when I have a free hour or two, but I have to remind myself that I have to make my own weekends.
Lately, I’ve been making sure I go to a workout class at a certain time every day or make time to get a drink with another freelance friend, so that I have built in self-care time. The good thing about the working world these days is lots of people freelance or have weird schedules, so it’s not too hard to find someone who can meet up with you at a wacky time or be cool with a coffee-work date on a Saturday.
More recently, you were covering celebrities as a staff writer for Vanity Fair — arguably one of the most glam jobs in the business. Was it as glam as it seemed?
In one of my interviews for the job, the deputy editor of the magazine asked me if I felt comfortable covering celebrities. I told her I had no problem and could easily have a conversation with anyone. This is true, but I know now that I didn’t quite get what she meant. She meant “Can you handle tricky publicists and their last-minute demands? Can you take the hint when a celebrity just does not want to go there, and can you course correct while still getting the interview you want?”
These were things I couldn’t have known until I worked at VF. The job can be glam, of course. When I worked the Met Gala red carpet, I captured Rihanna in her pope costume and Kris Jenner “you’re doing amazing sweetie-ing” Kylie Jenner. But that carpet is mostly one of observation for print and digital journalists; it’s not easy to snag an interview. It’s all about who you know and who is willing to take a moment to stop and chat before being whisked off to the front entrance.
I found on that carpet — and on any other — that I had to rely on a combination of my old-school journalism skills and inherent “Midwestern nice” and determination to make relationships happen. People will talk to you if you’re firm in who you are, what you want, and that you’re not going to waste their time.
And please, please, come to the carpet with thoughtful questions. They don’t have to answer your B.S. “what’s your guilty pleasure” queries, and if an editor is making you ask those questions, make sure you couch them between something original, time permitting.
What did you learn about covering celebrities that surprised you?
It’s like that snake analogy: They’re just as scared of you as you are of them. I’m not calling celebrities snakes, but the idea that they want to make a good impression on you is absolutely true. When they get on the phone or sit down to lunch with you, they’re working, too. They’re working to promote or advocate for something, and they want to get their message across just as much as you want to help them.
Before I do a big interview with someone I’ve admired for years, I always say, “I’m on the clock. I’m working.” I want to get the interview done and get it done well, so I just focus on that. The real pros jump right in, and I barely have to do any work. Jane Fonda answered follow-up questions before I could even get to them. But you just need to follow along with the tone the subject sets; if they’re more guarded, get ready to rely on your prepared questions.
Something else that surprised me was how good some people are. Some of the actresses I’ve admired since I was tiny have become people I want to make sure I say hello to at events and will always give me the time of day on the red carpet. I met one actress at a party and made a genuine connection with her; it led to one of my biggest features and a photo shoot I helped put together. She also asked for an invitation to my future wedding, and I’m not even engaged. I’m not saying that last part is normal, but I am saying you never know who you’re going to meet or what’s going to come from it, so don’t waste your time being shy!
Finally, you're leaving New York for Maine: tell us about your new gig, and how you feel about leaving!
At first, I was super nervous to leave New York and all the connections I’ve made here, but after the Great Media Layoffs of 2019, I decided it was time to decide what made me happy and if that meant staying in this city right now. I wasn’t necessarily trying get out of New York, but when I got the opportunity to interview for and accept a job as a digital editor at Bangor Daily News — a family owned statewide paper in Maine—I made the leap.
I have had a deep connection with Maine since I was a little kid (mostly because of Sarah, Plain and Tall), and my partner and I have always talked about living there. We originally meant we would make this move in our 50s, but this job allows me to still freelance with national publications and live in Portland, Maine, a city I love.
I’ve always been attracted to places that are beautiful but rugged and seemingly untenable at first — take New York, for example, so this seems like a perfect fit. We are ready for the challenge of a New England winter and excited for walks on rocky, windy beaches. I also get a lot more responsibility and creative freedom than I have at any job in New York so far. I will miss cocktail and networking events, but thankfully I have a pretty good base of contacts I can keep in touch with and will be back to the city often.
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Don’t forget to follow @Hilary_Weaver on Twitter, and go have an extremely unshy weekend.