Harling Ross

It was only with the rise of fashion blogs that I started to be able to envision the possibility of doing something in that space. I read so many of them. I miss Google Reader so much. I would check it every day. Blogs really cracked that world open for me—it suddenly felt more accessible, which I'm sure a lot of people would say. They demonstrated that someone like me could participate, if only online. All I had to do was buy a web domain and start typing, which is exactly what I did. I started my own blog. I don't think anyone read it except my mom and five other people. But it forced me to make a habit out of writing, and in doing so, I discovered what my voice sounded like. That, in turn, gave me more clarity about where that voice could potentially fit in. It's definitely a signal of a particular era to have had a blog.

I eventually submitted a 500-word essay to Man Repeller’s Monthly Writer's Club prompt. I think I submitted a few times, but then finally I got one published on the site. Man Repeller was so small at the time that I don’t think there was a ton of competition and it was easier for someone to really read it and respond. I started contributing here and there. That eventually opened up a conversation about working there.

I think they were in a pinch and they really needed someone to fill the role of their former social person who was leaving. I was three months into a new job at Estée Lauder, so I was really hesitant at first. It probably gave me a little bit of leverage actually, in that I was like, "I'll think about it," even though it was fully my dream job and I had read the website for years. 

I went to college in D.C. I honestly didn't like it very much. You know how people call college the best four years of their lives? That was not the case for me at all. I had a really difficult time making friends my freshman year. I was also really depressed. It was a very bad time for me, mental health-wise, which I think created a vicious cycle in which I was too depressed to make friends, and then I was depressed because I didn’t have any friends. 

Even though I did eventually make a few close friends, I never had a big “crew.” Sometimes I wish I could have a do-over and begin on a different foot. I know now I really isolated myself, especially at first. It wasn't like there were all these mean people and I didn't want to be friends with any of them. I just didn't really give myself a shot.

When I started college I was also struggling with an eating disorder, so in some ways it was in my own self-interest to isolate myself. Spending more time alone meant I didn't have to go out and drink or eat with other people. I just wish I could do freshman year over as a healthy person. But at the same time, I do try and talk about it because I know there's a lot of pressure for college to be this life-changing experience that sets you up for the rest of your life. And for me it wasn't that, but I turned out okay. My career is fine, my social life is fine. It didn't make or break things for me. If anything, it gave me a lot of empathy and made me less judgmental of people who might've had similar experiences. I'm not proud of this, but I do get a little satisfaction when someone from college who I wanted to be friends with follows me on Instagram. 

I've always thought of myself as someone who you need to meet twice. I have some social anxiety, I'm a little self-conscious. I really think about something before I say it, which might be why I prefer writing instead of saying things extemporaneously. But honestly, for all of its challenges or things that I don't like about it, social media has given me a place where I can highlight some of my more extroverted qualities in a way that I feel comfortable—compared to, say, an in-person interaction where I'm more self-conscious or I'm analyzing what I'm saying too much.

It's weird how social media almost collapses the timeline of getting to know someone, for better or for worse, in the sense that you think you can know someone just by scrolling through their feed. But it's also allowed me to put more of myself out there in an easily digestible way. In real life, I'm not funny on the first try most of the time. But because I've been able to be more extroverted on social media, that's impacted how confident I am in real life, too.

For the most part, it’s as accurate of a reflection of me as I think could exist online. I could be going through something personally that I'm not posting about, but that doesn't mean what I am posting about is inauthentic. Those two things can co-exist, which is disorienting sometimes.

I left Man Repeller in August. I gave a month's notice, so I had some time while I was still receiving a full-time paycheck to figure out what my freelance life could potentially look like. But I was still really nervous to do it, just because I knew from working there during the pandemic that most brands and media properties had slashed their budgets, especially their freelance budgets.

As a freelancer, I have three income streams, which are writing, brand consulting, and sponsored content on my Instagram. The sponsored content is a significant contributor, but it's also the one that I've put the most self-imposed limitations on because of how complex I’ve found my relationship with social media to be. 

It took me a little bit of time to figure out how to translate my skills and work experience into a freelance offering. But now that I've been doing it for six months, it's starting to get a little bit easier. Or at least I feel like it's decently consistent, which I feel grateful for. Honestly, the hardest thing by far for me has been not having colleagues to run things by and say "is this weird?” or “what would you do here?” or “can I get a second opinion?"

I feel fortunate that that's the hardest part because I know that for most freelancers, the hardest part is getting the kind of exposure that leads to paid work. That’s the main reason I've been trying to think of more ways to pay it forward, and create opportunities for other freelancers.

I started a freelancer Slack group. It's very new, and just getting warmed up. I'm excited to see where it goes and I hope it leads to a wider net of job opportunities, and that it might also make freelancing feel less lonely for anyone who participates. I know that's the benefit I'm getting out of it so far. I love Slack, and I really missed it—I mean, within reason. Certain aspects of it were toxic, at least in terms of my usage, but being able to chat with people on a pretty casual basis—I loved that. Now I'm getting to do that a little bit with other freelancers, which is fun.

It’s hard to be making so many decisions in a vacuum, which is what I feel like I'm doing a lot of the time. I start to doubt myself probably more than I otherwise would. Just to have someone affirming what you’re already doing, that can be really helpful, too.

Most people probably feel like an outsider to some extent when they’re early in their careers and starting out in a new industry, but I think media —and particularly fashion media—is structured in a way that really enforces that dynamic. Now that I’ve had a bit of distance, I can look back in hindsight and see that, at a certain point, I transitioned from being a media outsider to an insider in many respects: I had relationships with other people in the industry, I was getting invited to cool press events, I had influence within the company where I worked. But it’s still hard to shake the old mentality. 

I think part of this dissonance stemmed from the fact that I was coming of age in media at a company that was also coming of age, and in an industry that was changing rapidly. The particular stretch of when I worked full-time at Man Repeller not only coincided almost exactly with the four years that Trump was in office, but it also culminated in a very public implosion of the brand due to both financial constraints and criticism of the company culture and content. It’s evident that as much as I felt like an outsider at times, there were and are people in the industry who feel this much more acutely due to systemic racial, socioeconomic, and heteronormative barriers. I’ve always known this, but it’s become increasingly clear, and via new dimensions, the longer I’ve worked in media. 

Now that I’m a freelancer and working with a bunch of different clients in a variety of areas, I give a lot of thought to what power dynamics exist in these new spaces I’m entering. I ask myself how I can give some of my access to people who haven’t previously had it, while also examining why I’m the one who has this access in the first place. How did my existing privileges beget this additional privilege, and in what ways can understanding that help me carry them all more thoughtfully? I didn’t always ask these questions as a matter of routine, but now it’s a mindset that’s really important to me for any project I take on. And I’m grateful to colleagues and mentors who have set a great example of how to work generously.

I wouldn't characterize myself as a big weed smoker, because I don't do it often. I generally prefer other modes of chilling out like alcohol or a big slice of cake. Sugar's definitely my drug of choice, if I had to choose one for the rest of my life.

But I am really passionate about CBD. I’ve been a huge fan of Dusk for a long time. I take that almost nightly. I mean, if I'm feeling so tired and I know I'm going to fall asleep immediately, I don't take CBD. But most nights, that's not the case. I’ve struggled with insomnia for as long as I can remember. I am not one of those people who can get in bed and fall asleep immediately. My partner is, which is rage-inducing for me because I'm just so jealous.

I need a wind-down routine. I like to read for an hour, ideally, because I can't just shut off, CBD has just made it much easier for me to facilitate that transition. I first started using it a few years ago when I was doing research for an article. I was really skeptical at first because I'm not a big supplement person. I take a probiotic, but I'm not someone who has 80 gummies and vitamins every day. But after using it for a few weeks, it was really apparent to me that it actually made a huge difference in my sleep. So now I'm a CBD evangelist. I tell strangers on the sidewalk to use it. Aside from Dusk, I also like Not Pot because they have L-theanine in their gummies, and that's great for anxiety and stress reduction.

You know how now, if you go online and you're interested in skin care, you can find 500 million articles about skin care recommendations from experts and clinical dermatologists saying, "This is what you should be doing"? I feel like if that existed for weed, that would change everything for me. Because I find it a little overwhelming and I feel out of my depth. 

It was definitely the kind of thing that my parents would have really frowned upon if they had discovered me doing it. I was a goody two shoes in high school. It wasn't part of my social world. My high school was also kind of a weird environment. I went to a boarding school, and it was so strict that if you got caught doing something like that, you would be kicked out. I think because the stakes were so high, I had such an innocent high school experience. No drinking, no drugs. That probably shaped things for me too, where at a time when other people are experimenting, I was dancing completely sober in a brightly lit room.

This interview has been edited and condensed for clarity. Harling Ross photographed by Meghan Marin at her home in New York. If you like this Conversation, please feel free to share it with friends or enemies. Subscribe to our newsletter here.