How they made it: The Molehill's Viv Chen on career transitions and fashion writing

creativity, security, and changing careers in your late 20s

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Hi! Viv is my first guest for a series called “How They Made It” which is about interesting people I encounter and things they've created, whether career-related or relational. I want to talk to her because she used to work in public health but has forged an awesome career in fashion writing in the past few years. Viv writes The Molehill, a very successful fashion publication on Substack. She's also a freelance fashion writer who's been published in Vogue, SSENSE, The Strategist, Coveteur, and more.

Some things we discuss in the interview:

• Viv’s transition from public health to fashion writing: “I think it's just hard to know how much money you can make and no one really likes to talk about it and people are not super open about it. So I told myself that I want to treat this as a period where I can just create and experiment…”

• How Viv balances content creation, Substack writing, and writing for magazines: “I think we are now in an era where having a good Substack where you can really show your portfolio and your voice and your audience interest has essentially become a portfolio.”

• How she learned to pitch: “It really is just the nature of the work. I now kind of think of it as, if I'm not getting rejected a good chunk of the time, am I even really putting myself out there creatively?”

• How Viv figured out her content strategy on Substack: “A rule that I follow is I just don't want to force anything because I also think readers are really smart and they would rather read an essay about dryer balls where I'm genuinely interested or excited to talk about it than say, a secondhand roundup where I'm clearly dialing it in.”

• How metrics-driven Viv is with Substack writing + how it ties into monthly finances: “My incremental goals are for The Molehill to grow in the right direction. I wouldn't say I dream of having X number of readers. But I think that over a long period of time, gradual upward growth of more readers is generally a good sign that your writing is being read by more people.”

• What she would tell her younger self: “I don't like to use the word "risk-averse" because I feel like in the creative space people always talk about needing to take risks, but I actually think sometimes the opposite - risk aversion can actually really support creativity.”

I really enjoyed talking to Viv, who is an incredibly talented writer and creative with a pragmatic side that I relate to as an eldest immigrant daughter. Hope you guys enjoy it too :)

AVA: So, you started fashion writing in your late 20s. I know you used to work in public health, you got burned out and slowly transitioned to fashion writing, starting with Instagram. You mentioned that you kept your full-time job for a while before you actually made the leap to this new career. I'd love to hear about the period of starting to experiment with content creation and fashion writing while still having a job. How did that transition end up happening and how did it feel?

VIV: This was during the pandemic, around 2020 or 2021. I started posting fashion outfits, like fashion thoughts and pictures with my outfits on Instagram. I feel like everyone who starts posting outfits on Instagram will say, I'm just doing this for fun. It’s tempting to say I had no expectations at the beginning and to an extent that's true because I think a career as a creator where it's financially sustainable is such a gamble, it's like a flash in the pan or whatever. So I was not counting on it, but I also feel like no one really starts posting their creative output on a consistent basis unless there is a seed of, I would like this to grow into something more impactful one day.

I was posting outfits and I thought it was cool when I saw new people were following or new people who I had never met before were commenting saying like, “Oh, I love how you mix this Sandy Liang fleece with these Mara Hoffman pants.”

Since it was the pandemic, I was really enjoying that online community because I wasn't going to work in person and, well, the Bay Area isn’t particularly a street style capital, but no matter where you are there is street style by nature of there being streets. My Instagram account grew, and I started getting small brand deals, nothing that would pay my bills. But it was really exciting at first. Like, oh my God, this brand wants to pay me like $500 to make this video and I was really uneducated on usage rights and what I should be charging. When you start out as a novice without an agency or anything like that it's hard to navigate and I was just pumped that I could make a little money and spend it on the clothes I wanted.

At the same time, I was feeling more drawn to fashion discussion, fashion analysis. I've always loved history, journalism, sociology, anthropology from my college liberal arts background. So I always felt like I was seeking out other fashion creators and writers who saw fashion in a more analytical sense and would pull in topics like classism or racism, like those types of frameworks and analyses into clothes. That's genuinely like the core of what I'm interested in. I am an intellectually motivated person and if you post a deep dive on the history of swimsuits, I love reading stuff like that or, you know, contextualizing, like someone's collection in the current political climate. So that was the impulse I followed in starting The Molehill while working full-time.

During this time, my career in public health was in a good place. I was good at it and I got along with my coworkers, but I'd just been working like in the public sector throughout COVID, it was just very intense. And I was feeling so much more excited about the intersection of fashion and sociology. So I knew a big transition had to be made.

Part of it was kind of feeling like, I'm in my late 20s, I worked throughout college and I worked immediately after college and I've never taken like a real break, I guess, to assess changing interests. I felt there were peers around me who were taking career breaks or like getting a master's and I was thinking I should do that for myself even though it is such a risk and I did not know at that point whether or not doing a mix of fashion content creation and fashion writing would really pay my bills.

I think it's just hard to know how much money you can make and no one really likes to talk about it and people are not super open about it. So I told myself that I want to treat this as a period where I can just like create and experiment and I want to have saved up enough that I'm not going to be extremely stressed out every day or month to month. Almost like, I'm gonna self-fund a fellowship for myself by being really intentional about saving up enough in my last year of full-time work. And planning for a year, a year and a half what those base expenses are and mentally preparing myself. That was key for me to take the leap—have I saved up enough to make sure I can really feel free to explore? I've heard so many stories from people who are just so stressed from the financial anxiety that the creativity can't come because you're trying to scrape it all together. So, not to say that there wasn't like so much hustle from the moment that I did leave my job, but it definitely took the pressure off knowing I gave myself enough runway to make this enjoyable.

AVA: I know you have three different channels. You’re a freelance writer, you have The Molehill and then you also still post on Instagram. Did you start all three of these things around the same time? Was there one particular thing where you were like, this is taking off and this is providing more of a feeling of something is working? How do the different things that have constitute your writing life now come together?

VIV: Yeah, I would say that the phases were quite marked in a way where I started out with fashion content creation. I would accept certain brand deals with brands that I liked, taking pictures and writing brief copy for a reel or post. And then around late 2021 I started feeling, content creation is fun but I don't find it intellectually very stimulating or sustainable for the long run. So I started on Substack.

I was really nervous about writing that first piece because I have some perfectionist tendencies and I felt like this piece has to be so good, it's the first one. I definitely felt nervous about putting myself out there because there's natural self-consciousness when you take a creative leap and people are kind of thinking, what is this? Like she's doing something kind of different. But I loved writing the Polly Pocket piece and looking back, I'm like, wow, my voice has come a long way, but even back then I was just kind of following that North Star of loving the more analytical side of fashion.

For freelance writing, I never had newsroom experience, I've never interned. But I was really curious about these things. That was something completely new I had learned about through other freelance writers and through Substack. I need to fact check when my first byline came out, but probably not until 2023. It really took some time, I think, for editors to view Substack writing as a legitimate portfolio as opposed to "you need a clip in this magazine to get a clip in that magazine."

I think we are now in an era where having a good Substack where you can really show your portfolio and your voice and your audience interest has essentially become a portfolio, a Muck Rack of sorts, the modern Muck Rack. Editors now sometimes reach out to me and just say, "Hey, I read your Substack, I really like it. If you ever fancy writing for us, my inbox is open."

So now I do select freelance writing. It does not pay as well as Substack or brand deals just because outlets, most media companies just don't have the budgets. What I get out of writing for magazines is the chance to work with an editor and have someone whose thought and storytelling I admire, who I can learn from. I think it's a gift to be edited because I am a one-woman show for my newsletter so I never really get the chance to get that sort of line-by-line mentorship.

AVA: I saw a Q&A that you did on your Substack that you were pitching stories to outlets for almost a year before getting a yes, and I was curious about that process. It sounds from what you're saying now that some of that was also that it took a while for editors to understand Substack as a thing. But were you actually like actively pitching for a year, or was it more sporadic? What was that process of learning to pitch like? I think fr a lot of people who are writing on Substack or thinking about going freelance, it's very intimidating to be like, "How do I do this thing that I've never done before," especially if you have no experience working in a newsroom.

VIV: Yeah, definitely. It was very sporadic because I would read fashion magazines and think, "Oh, I have a story idea that is very much in the spirit of how this magazine talked about trend analysis or interviewing someone in the fashion industry." So I looked up some magazines' pitch rubrics or pitch guidelines. I learned every magazine, every editor can be kind of picky about what they want in an email, what catches their attention.