On evolving in your creative life

You’re a self-employed writer and have a weekly newsletter, but let’s start from the beginning. One of your first jobs was in HR. What made you choose that path initially?

HR was my third full-time job after school. And I went into it because I got fired for my second job as an office manager. I was doing new hire welcome packages, buying toilet paper, but also helping budget for events and ordering pizza for meetings—this crazy wide gamut. I did not do well in that sort of generalized role.

I thought I was doing well, but I didn’t like it. And when my asshole boss fired me, he actually told me that I should be a writer, which I did not take seriously at all. Guess you can be an asshole and be right at the same time.

Was there something about the first job that had to do with writing that made your boss think you should be a writer?

Well, I started doing these interviews for the company’s blog. I think I was trying to bring “creativity” into my role. Creativity was always just a side project for me. I didn’t emphasize it, but I knew that I always wanted to be it. I didn’t even know what it meant, but I decided to do the blog interviews of all our employees. And they were really playful and I put a lot of work into them and he really liked them. They obviously weren’t making us any money. But when I ended up leaving, I think that was what made him say I should pursue that path. At the time, the idea of being a writer was so alien to me. I thought writers lived in cabins and wrote novels.

I didn’t have a concept of a young person working in media, writing little articles. That was just so far from my reality. I was living in Silicon Valley, I didn’t really grow up or go to school with anyone who wanted to work in media. It was a totally foreign world to me. And no part of me even considered writing when he said that.

Yeah, that’s so interesting that he saw that in you. There seems to be a common thread with artists in general who get out of school and then are like, “Okay, I need to feed myself.” And then if you’re doing something that’s not related to your art, it almost follows you in that way and forces you to make time for it. It’s cool to see how your path has gone from that to what you’re doing now—and how it was always kind of there. How did you make the jump from HR to your role at as an editor at Man Repeller?

So those three years I spent in HR, I was sort of debating whether I could spend my whole life in this career. At that age, you’re just projecting your entire future. And you assume that whatever you’re doing then is going to last forever. I kept imagining being in HR forever and it would just give me this horrible pit in my stomach. And that’s when I really started, I was half committed to HR and the other half I was really trying to find a different path for myself. I was really lost as to what that could be. I was just doing random jobs—anything that was half creative.

I didn’t think that I was entitled to a full creative job because I had a business degree, so I was trying to find what that middle ground was. But I met somebody—a new friend in San Francisco—who was opening her own store and had friends who were full-time creatives. That was my first exposure to those types of people. I think that gave me a boost to start thinking of myself in those potential terms. I’d been a Tumblr girl for years, but I started writing a blog more seriously. And I was a huge Man Repeller fan and I heard on a podcast Leandra say that they were losing people and it was really hard to find people. Because of all the things that led me up to that point, I imagined, what if I could be that person?

I remember the exact moment I was driving in my car and I don’t even know what made me think that could possibly be me. But I thought I could just get them coffee even. I didn’t really see myself in those terms, but I sent in writing samples to show my personality. And instead, she latched onto the writing and was like, “Would you like to come be a junior editor here?” And that’s kind of the classic career-hinging moment of crying in a coffee shop and being like, “I’m going to leave San Francisco, I’m moving to New York. I’m quitting, I’m breaking my lease. Might be breaking my relationship up. Everything’s changing.”

I was there for four years. By the time I left, I was in a completely different place. I had a lot of responsibility for the editorial team and the editorial output. And at that time, I had also become sort of a pseudo-influencer because a lot of the employees at Man Repeller were straddling those worlds of editorial and influencing. The readers at Man Repeller had such an intense relationship with the writers. It was such an intense transition of going from just this kind of unknown HR girl to this person who felt a little overly watched.

I started to ask more of myself on a writing level. Before I was just like, “Be grateful that you’re writing about a dentist,” to getting to the point of being like, “Oh, is the writing I’m doing here serving a higher purpose? Is it satisfying me? Does it line up with the principles and values that are starting to form in my worldview as an adult?”

I started there when I was 26, I left when I was 30. And those were just big years. I also started to doubt influencing in general. I didn’t really ever want to be an influencer. I started taking on the paid work because I needed the extra income. And my dream by the end was to not need that extra income and to never influence again. It’s so funny to use that term that way. Because it really just means selling the attention of your followers to corporations.

It’s always framed as this sort personal choice when it’s not. It’s actually a choice you’re making for your entire audience. And I didn’t really feel comfortable with that after a while, considering the type of writing I wanted to do, which was going to be more critical of the influence of corporate interest and more critical of influencing generally and the commodification of the self that’s come to be so prevalent in how we communicate and perceive ourselves.

So, leaving was a big leap and also an exciting one. And it just happened to perfectly coincide with the beginning of COVID. My last day there, which we had planned a month or six weeks in advance, happened to be the day that everything shut down in New York.

Well, that worked out in a weird way.

It did, but at first, it didn’t feel like it because all freelance budgets were suddenly slashed when I was supposed to be reaching out to editors with pitches.” Suddenly nobody was writing about anything except COVID which I felt ill-equipped to cover. So, I did have a moment of having leapt and realizing that the entire landscape I thought I was leaping into was changing underneath me. That was a little scary for a minute. It was so far from the worst problem to have during that time. It was just a little unmooring in terms of where I was going to get money. But I figured it out when I launched my newsletter.

Right. I mean, there’s so much here about what you were saying in regard to the evolution of yourself as a writer and how you started really being like, “I don’t deserve this. I’ll get coffee for you or whatever instead.” A lot of the time, we grow up learning about writing careers in such a specific way. So you choose other options and then you’re like, “Okay, maybe I can make a career out of this that may not be staying in a log cabin remotely and writing the Great American Novel.” But then you ended up a place years later where you really owned your writing skill. And you were a writer and editor at a big beloved media company.

I recently listened to one of your podcast episodes where someone called in and they were worried about a fact that they hadn’t gotten to a certain milestone in their life. You spoke about how silly it was to put all of that pressure on yourself as a creative. How did you realize that everyone is on their own journey, and how do you view competition within the creative sphere?

That’s a great question. The person who said something to me that really changed the way I thought about this is my friend Verena von Pfetten, she was actually my very first editor at Man Repeller and now she’s one of the co-founders of Gossamer Magazine. She’s full of wisdom and I have always really appreciated her perspective because she’s worked in the industry much longer than I have. I think she’s just a little bit jaded in all the right ways. Something that she said to me when I was talking to her about the arc of a career is that so many of her peers who she felt were miles ahead of her when she was young—the sort of people who were editors in chief by 26 and those crazy early milestones or early success. She went on to watch them go through plenty of cycles of coming off that pedestal and struggling to find something else that fit, and then finding it, and then losing it. Having those exact same rhythms happen in her own life made her realize that early success doesn’t really promise later success. And that helped me understand the extent to which life is cyclical in general. You’ll have times when your career’s going really well and this goes for friendships or relationships, your social world, your hobbies, your sense of self. Any pillar of your life will just constantly be cycling through ebbs and flows. Comparing yourself with your peers is often futile because you’re bound to be in different parts of the cycle at different times. And so when you are down and your friend is up, inevitably that will invert at some point. And so focusing on getting through your own process is much more useful. It helped me appreciate that there wasn’t sort of a goal, it was more just like, “How do I learn to breathe through the ebbs and flows of my life? How do I appreciate the cyclical process of feeling grounded and certain in where I am and then feeling ungrounded and uncertain about what I want?” And then finding it again and figuring out who I am through that repetitive process.

Viewing my life through that lens has helped me be more embracing of uncertainty or moments of ambiguity in my life. It’s made me trust myself through that process a lot. I mean, not to be too heavy-handed about the metaphor, but I find that with my newsletter, for instance, I’m writing an essay every week and I go through a mini version of this process every single week where I feel lost, uncertain about what I can do, not confident that I can do it, and then getting through the process and being like, “I did it, and now I feel confident again.” And it’s almost amusing watching myself go through this process every single week. It’s unavoidable and it feels like this great metaphor for how life is generally. It’s like, no matter how great of an essay I can write and how confident I can feel in it, I’m going to lose that feeling again when I’m faced with another creative challenge.

And same goes for when I feel like I’m writing like shit. It doesn’t make the fear go away, but it does make it feel less threatening to my whole life. The point I made earlier about being 24 and assuming that everything that was happening then was going to happen forever. I don’t have that sense anymore. I really have a sense for the transience and cyclical nature of life. And it can be unmooring because it makes me understand that things aren’t going to last. The feelings I’m having now will go away and be replaced with other ones. But I think it’s worth losing that kind of delusion of certainty because I feel more trusting in general.

As prosaic as it sounds, I feel that having humility for the moments when you’re up and acceptance when you’re down is the main challenge of life itself.

Right. And I think the more you practice that, the more freeing it can be for you and your creative practice of just realizing that even though you may have a certain level of success, you can still feel this. Because I’m sure young writers today maybe read your work and have followed your work for a while and are like, “Oh my gosh, she feels this. I can’t believe it.” But I think it’s just a good reminder that we’re all people and we all have these feelings.

If you’re constantly comfortable in your creative work, you’re probably just repeating what you’ve already done well.

So, I think that it also can be a really good sign if you’re doing creative work and you feel afraid. It technically means you’re moving forward and trying something new. And I think that’s the only way to live as a creative, like be alive with whatever you’re making.

I love the part of your newsletter where you list 15 things you’ve consumed that week. How important is consuming things for your creative process and writing process?

I think it’s super important. The relationship between input and output is very symbiotic. You really can’t keep putting things out if you’re not taking things in. And this was something I ran into a lot with working for a traditional media site. I was putting so much out all the time that my ideas were getting stale. I just wasn’t taking enough in. I didn’t have the time or the energy to take things in. And so when I transitioned to working for myself, that was something I really wanted to make sure I left time for. I feel there’s definitely a difference between quality consuming and low-quality distraction, which I definitely partake in as well.

I really cherish getting to take more things in and take more time to write my newsletter than I ever took with the writing I was doing for at a full-time media site. It’s been really interesting to compare and contrast those things.

I find that it’s really difficult to get creative work done without a deadline. So, I do think that the sort of white-knuckling that’s kind of definitional of the media industry has been true for me. I need to put that level of pressure on myself to get stuff done.

What hasn’t been helpful is the idea that pressure always creates better work. I think there’s a limit. And I think getting out of full-time media work and getting to set my own hours and setting my own pace has made me realize how important having time and your basic emotional needs met is.

It cannot be discounted how much that does for one’s creative ability. So, getting to take some of that back for myself, time to watch movies or read books and do things that I felt like I was constantly having to cut away from to make time for more output has been such a gift of working for myself. I’ve never felt so clearly that my mental wellness leads to the healthy continuation of my job. When I was working for other people, that connection was much more distant. My suffering could actually lead to more success for the business. And I really enjoy that not being possible with my job now. It doesn’t work if I’m miserable. It’s been a nice opportunity to value some of those things that don’t directly make money for me, but really do fuel my creative life in ways that are less obvious and direct.