On getting your work out into the world

Let’s start off with the big self publishing projects you’ve done this year: your “What is Lifestyle?” piece, and your work with Kyle Chayka on Dirt. How did that process start for you? Considering the transition from traditional publishing to figuring out how to create a vessel for pieces that didn’t fit into that framework?

I had a piece about the concept of lifestyle that I was working through for a while. I was looking at the origin of lifestyle and the fact that the word “lifestyle” came about in the early 1900s and then started being increasingly used during the mid century when lifestyle was really being marketed for the first time. There was a huge increase in the dissemination of images that people looked at and tried to determine what lifestyle they were supposed to aspire to.

It was taking this word and the origin of the word, but then following all of these threads through photography, marketing, architecture, and technology. I was really working on it just for myself. But once I got it into a coherent form, I was so eager to share it because I felt like the word, especially during the pandemic, was coming up all the time.

I found a home for the essay, but then it ended up falling through. At that point it was very close to the presidential election, so I felt like I had a choice between trying to place the essay somewhere else, or self-publishing it as sort of a Hail Mary.

What are the pros and cons of self-publishing?

I think what a lot of people are worried about is that if we self-publish, that other people see it as an act of desperation rather than an act of agency, because we don’t necessarily know how we’ll be perceived.

I just sort of waited to see whether it landed, and it did. It got picked up by Longform, which was something that I had aspired to for a long time. I ended up finding my agent through an editor who really admired the piece and was able to put me in touch with her. The concern that people would see as an act of desperation is unfounded because people did see it as an act of agency. And I’ve heard from other writers that it emboldened them to also self-publish, or they’ve come to me for advice.

What type of advice did they ask you for?

Some people thought that I had paid somebody else to build the website. And I was like, “Oh no, I built it myself. You know, you could do the same thing or I can help you.” I go back and forth, because obviously, I do believe that there’s a value in legacy publications, not just perceived just like a history and also an infrastructure of people that are really important to the success of a piece, like really great editors, really great fact checkers, really great copy editors.

I don’t want to give the impression that I don’t think I need an editor because I think everyone could use an editor, but there are things about the process of trying to get published that have nothing to do with the work, that can really hinder your ability to have an idea and get it in front of people who it’s going to be meaningful to.

Absolutely. What have you found to be the most hindering aspects of traditional publishing?

It can be delays in getting paid or people moving around their jobs, or an editor just not having it in their freelance budget. I think I’ve hit a balance of knowing when is it strategic to try to shape my writing and my ideas to a preexisting framework, and when is it better to just break the mold.

And you’ve done that more since “What is Lifestyle?,” right?

I have a Substack that was started by my friend, Kyle Chayka. He asked me to be sort of the primary contributor, it’s called Dirt. I don’t really remember how we came up with that name, but it’s fun, it’s playful, it’s irreverent, it hints at the fact that a lot of the things we cover are a little bit amorphous.

I did a long piece about growing up in the suburbs and seeing my experience reflected on Tik Tok in a way that I never really saw reflected in literature. That piece took off and was read by probably four times the number of people that actually subscribed to the Substack because it was amplified through Longform and other newsletters. I was really humbled by that experience.

I should probably give the caveat that I also have a full-time job right now. Self publishing does require a certain degree of financial independence because you might have to invest a little bit of money. For “What Is Lifestyle?,” I invested a lot of unpaid time upfront, and did not make any money off of it. I pay about $16 a month to maintain the website. Dirt, we don’t have paid subscriptions right now, and I paid for a fact checker. But I think for anyone who is in the position to put their work out there, and if you can afford not to make money on it in the short term, or you see a way that it might lead to more paid opportunities for you, which these pieces have for me, at least, that it’s worth it.

Planting your flag in this topic, not for your own pride necessarily, but because observing something that has an element of truth to it about the culture and being able to share it with other people in a way that allows them to understand something about themselves and their environment that they had observed, but didn’t have the words to put to it. That’s the highest praise I can get for my writing. Self-publishing is a really important tool to have in your toolbox as a means to that.

The Dirt piece that I wrote about growing up in the suburbs, I’ve never received so many letters about something that I’ve written. I was really humbled by the feedback that I got, and I think a lot of people that wrote to me preface it by saying that they thought that I probably heard from people all the time, and I don’t. I think maybe people who don’t write think writers get a lot of feedback on their writing, and a lot of them…

Oh yeah. Most people definitely don’t.

I was so happy to hear from people who said that I had captured their adolescence and teenager hood in a way that they hadn’t been able to. I actually heard from people from my past that I had gone to school with and hadn’t necessarily been close with, that took that opportunity to tell me that they follow my career closely.

I just never would have known. I think my message to people who are considering doing this, and are in a position to do it financially, is have faith in the strength of your own ideas and also have the courage to take that leap, because worst case scenario, not as many people read it as you wanted them to, but you still have done the work and put the work out there.

What do you think of your years working in traditional media jobs or just publishing on the internet? What skills from that were most important to you in self-publishing?

Well, I have written a lot of Twitter copy in my life. My day job in media has always been in audience development. Maybe my strength is in knowing how to package the story for various social media platforms, which carries over to knowing how to come up with a very compelling title, and description and dek for things, because I’ve done that for other people’s work for so long at various media companies.

That’s always been a huge part of my work. In learning and being paid to package other people’s work, I’ve gotten better at packaging my own, even down to calling this large piece about lifestyle simply “What Is Lifestyle?”

Another benefit of writing for yourself and not other people, is when you freelance for a site, they don’t tell you how many people read the article, or where they came from or what other websites linked to it. Because I built the website for “What Is Lifestyle?,” I can see all of that. When you freelance, you have to kind of figure it out in other ways.

Right, detective or suss it out. Yeah.

It actually is kind of a professional hindrance because, if you had one of the top articles at a place that you freelanced for, for that month or that year, and you don’t know, that’s an accolade that you’re not able to add to your resume, which is a bummer. But I can see everyone who comes to “What Is Lifestyle?,” and a lot of them come from Google, from Googling, what is lifestyle? I unintentionally created an extremely SEO friendly platform for myself.

In a perfect world, there would be lots of websites that wanted to pay all the talented writers, for every niche area of thought. But something that I’ve definitely struggled with is realizing how few websites are publishing work in the areas that me and my friends care about. Obviously everybody’s dream is to get paid. I don’t know what the high end of it is—$5,000 for an amazing piece or whatever—but of course that is so rarely possible. What do you think about the field of opportunities available right now to writers?

I’ve heard a lot of people say, “I miss The Awl”. When they say, “I miss The Awl,” what they really mean is “I miss having a place for my wacky, weird, unconventional ideas. Or my long form essays and pieces that don’t fit into the categories and rubrics that exist at other places.”

There’s a lot of publications that I admire and look up to. But when I was working on my lifestyle piece or my pieces for Dirt, I didn’t start writing it with a certain publication in mind. One skill that you pick up as a freelancer, when you do need to rely on that freelance income to get paid, is to begin to write in the voice of those publications. It’s very different from writing for yourself.

When you write something for yourself and it’s finished, and then you ask, “Where does this fit in?” And you look around and think, “Oh, not really anywhere,” that’s a scary moment, but that doesn’t mean there’s no value in it. It means that there’s a hole in the landscape as you’ve identified, for really strong, important work.

The most I’ve been paid for a piece ever was in Playboy print. I had a wonderful rapport with the editor in chief there. I was able to call him up on the phone and tell him his wacky idea and pitch him on sending me to Lithuania and he said yes. One of the best experiences I’ve ever had. And within a couple of months he had left Playboy and then actually Playboy, stopped doing print during the pandemic. So, even when you were able to build relationships and the trust with the editor who will let you take risks and they know you and they trust you to be a little bit more experimental, there’s other factors that could change those circumstances.

I think that’s pretty much most of the time the case. How many editors do we know who have stayed at the same position for more than two years? Not that many.

Right, and I don’t blame them.

All the editors I know who have left jobs have left them for very good reasons. Whether or not they were laid off or if they just chose to leave because it was an unsustainable work environment. I would never tell someone “Oh, please stay at your job that’s horrible so that you can keep publishing my friends.” How has self-publishing changed your definition of success in the writerly world or just even in the creative arts world in general?

I don’t know that it changed my definition of success, but it reinforced something that I already believed, which is that your most lasting relationship in media will be to yourself and to your writing. If you can’t uphold a certain level of integrity, not just towards the ideas that you believe are good and your faith in them, but in the way that you treat other people and in the way that you allow other people to treat you, then you will have to do a lot of work eventually, once you realize how much has been compromised.

Other than the most important relationship being with yourself, and your writing, it’s the way that you treat your peers, and the way that you treat people who don’t have power in the industry. But I have had the best opportunities available to me have come to me through peers, people who are the same age and experience level as me.

That definitely makes sense.

The outcome of that work is going to be hinged on the quality of that work, but also how people feel about you. The karma you’ve accrued, the way that you treat other people, whether you stand by your ideas, whether you’re an independent and critical thinker about some of the more toxic elements of the industry and the inequalities in the industry….This all goes into what success means. Maybe it doesn’t mean selling the most books, but at least you know that you’ve left a positive impact on other people, intellectually, emotionally, financially, spiritually.

I am not staying up at night, wondering, “Am I going to be remembered?” It’s more, “What will I be remembered and known for?” And I hope it’s for being a good person and a thoughtful person in addition to being a thoughtful writer.