In our long-running series, "How I'm Making It," we talk to people making a living in the fashion and beauty industries about how they broke in and found success.
The first thing to know about Choire Sicha is that his name is pronounced "Cory." The second thing to know about Choire Sicha is that he's incredibly funny and quick-witted, especially when it comes to talking about himself.
"As you can see, there's a narrative strain here in that none of this had any planning whatsoever," he says with a big laugh in the middle of explaining his previous jobs. "Just so we're clear, none of this happened with any sense of purpose or direction or thought to good ideas."
Sicha is referring to his nontraditional career path, which kicked off after he skipped out on going to college. Instead, he had "a lot of jobs": A call center gig, scooping ice cream, serving up drinks, waiting tables, making "a lot of coffee," time spent working at a homeless shelter in San Francisco. But during that time, he started blogging on the side, exploring a relatively new form of media available on the internet. That would eventually land him a position at Gawker and a place in the media industry.
Now, in his role as editor of the Styles section, Sicha is bringing new voices and perspectives to The New York Times. We hopped on the phone with Sicha ahead of fashion month to get his thoughts on the changes happening in media, how he plans on tackling fashion in the pages of the Times and what he looks for in new writers. (Write this down: "Dutiful stories are sad stories.")
When were you first interested in working in media?
I'm still not sure that I'm totally interested in working in media, but since I'm here! [Laughs] I always wanted to be a writer when I was younger, but I didn't think it was ever possible, and so I didn't take it seriously or actually even really think about it. This happens, I think, in a lot of fields, including fashion and media and TV, things that seem exciting and far away when you're young.
What first connected you with fashion?
I grew up in a particular time when self expression was really tribal. I went to a high school outside Chicago where people had a lot of different visually expressed identities, and we made ourselves look in ways that helped us identify ourselves to each other, I guess you'd say. We shopped at thrift stores for clothes, wore combat boots, and put eggs and food color in our hair. We were trying just to be ourselves.
One of the things I love about now is you see 8 year olds and 40 year olds with red mohawks on the subway, and they're just doing them and self-expressing in a very wonderful way. When I was younger, those were fraught, and you would get beat up over the way you would look; that sort of self-expression was new to society, I think, and it was challenging. It's cool to see it come into its own and to see that we're much more free about how we present ourselves to the world now.
How did you get started in your career?
One thing about not going to college is that there's no feeder system for people into work places if you don't go to college. The studies show that people who don't go to college have lower income for long periods of time — decades and lifetimes — than people that do go to college, because there's no pipeline for them and also because they started in jobs that don't pay as well. It took me another 10 or 15 years to accidentally start working in journalism.
I was an art dealer for a number of years, for a friend, and after that I was blogging for fun on the side. I was co-writing a blog with a friend who lived on the West Coast and learning how to write by writing in public — which, actually, I sort of take for granted now. That was a new thing, then. We were just sort of messing around on the internet, which was a kind of quiet place.
What were those early days of digital media like?
They were pretty small. When Elizabeth Spiers started Gawker, it was very 10-to-5, because it was for people who worked at their desks; we didn't have iPhones. It was also pretty quiet. There wasn't a ton of online media, and what there was was sort of confused, or very second-tier for the publishing companies that did have media presences online. But it was fun. The thing about it then, there were no tools; it was like sending letters into the vacuum. You'd get emails back, but there was no other real way to know who was reading you or why they're reading you or what they were getting out of it. Unlike now, where you hear about it every five minutes.
Nick Denton initially hired me to write for a site he was about to launch called Flesh Bot, which was intended to be a site about adult things. I did not want to do that. [Laughs] And fortunately, Elizabeth Spiers retired before that site launched so he instead was like, "Oh, you're here. Just take over Gawker when Elizabeth leaves." We got paid $24,000 a year and we were supposed to write eight or 12 posts a day, I can't remember now.
What did you learn about working in media on that job?
I learned a lot of things on that job. One of the things I learned was you should never, ever be mean when people die. Since Gawker was a commentary site, we didn't do much reporting. When we did, it was great. When you're writing commentary all day, you start to lose focus on why you're writing, what you're writing, what it all means — and you go astray. And also, we didn't have editors; we didn't have other people in the office to talk to even, really, in the early days. So, I learned not to make fun of people who were ill or dying.
This is boring, but the greatest thing for me — and I see this with young writers sometimes, that they don't have — is I had to write constantly. It was very good on a sentence-by-sentence level and at establishing voice. Most of voice is just a series of crutches applied regularly, and when you're writing eight-12 posts a day, you really double down on that. What I see with young writers now is that they don't have these horrible blogging jobs — which is for the best, probably — but they also are hesitant. Their voices aren't fully developed. They aren't put on the spot so they don't develop as quickly, probably.
What made you decide to launch The Awl and its suite of sites?
By then, some time had passed. I didn't stay at Gawker that long the first time. I went to work at the Observer; I freelanced for a while. One of my first contract jobs was writing listings for Arts & Leisure here for Jodi Kantor and Ariel Kaminer, and they're both still doing very well. That actually was an amazing strength for me, too, as a writer, because I was writing constantly and writing tiny sentences, but they were going through three or four layers of editing every week. That taught me how to be not a jerk and how to be humble and how to not get too attached to things.
And then, if you'll recall, the world sort of went to heck in a hand basket. I was a pretty active freelancer; there was a time when things would fall into your lap and people would be like, "Here, write this, write that." And that stuff all dried up and blew away, pretty much all at once. We had nothing else to do, so we just decided we should start our own website.
What was it like to build that from scratch?
Well, it was surprisingly easy because you buy a URL and then you just start doing it. Now, the real secret to The Awl and its other site existing for a long time: One was that my business partner, Alex Balk, was diligent. He'd always been at Gawker, too, and he would get up and start the blogging machine. He was always there writing posts for better or for worse. And the other secret to that place existing for nine years is that we have a third business partner named David Cho, who, later, was the publisher of Grantland, who was responsible for the business end, so we weren't just two editorial idiots in a room blogging into the void. We had someone whose full-time job was saying, "How do we make this into a business? What should this company become? How are we going to make money?"
How did you decide to leave?
I think I was there for about five years all told, just at The Awl alone. The Awl grew up. We made good money; it made seven figures a year. It was very healthy. Then after a long period there, I was itchy. I had moved towards administration. By the end there, we had hired strong-enough editors and they were all running these websites. Then I realized that — and I think this happens to a lot of founders — I was the one writing the checks, making sure things were going and cleaning the bathrooms. It was in good enough shape that I could say, "Maybe I want to try something else."
So, I started looking for a job, which I hadn't had in a very long time. I tried to hire a woman named Melissa Bell from the Washington Post to run The Awl. I was having coffee with her while I was looking for a job, and I was like, "Maybe you should find me a job," and she was like "ha ha," and then she was like, "Wait, I have this really dumb idea that you should come work here." I did for a year and a half and really loved it. I got to work in a way that taught me a lot; I got to work between the product teams, the revenue teams and the editorial teams, which was really fun to get a deep view into a growing, very intelligent new media business.
I was also under-qualified to have such a job, which was sort of delightful and fun, too. The joy of media is it's not like you have a list of qualifications on a resume and you think, "Aha, we have found the person for this job!" It's like, "Well, we've got to try new things; this is an industry in change. Let's find somebody who wants to work really hard and can communicate with other human beings and is willing to try some stuff."
What attracted you to the job at The New York Times?
I was a little lonely for editing and editorials. One of the things I loved about The Awl, whether it was working with our editors or with our freelancers, was we got to break new voices. We got to be a feeder farm for larger publications, sort of a rural baseball league team, and we got to try things that no one did. One of the things about the Styles section and the Styles desk here is that this can be a place, and is a place, for writers to get a start; for writers from other markets in the country and in the world to write for the Times for the first time, and to introduce a pipeline for emerging and entering-mid-career writers from pipelines that are not, let's say, a direct line from private school and Harvard.
What are some of your goals in the position?
At The Awl, and at Vox, too, I became a real proponent of doing and showing rather than talking about things in advance, so it makes me sort of a bad interview on this topic because I want you in six months to say, "Oh, this thing has changed in this way that I recognized." Or, "Hey, my friends are talking about this thing they saw or this new thing that they were trying." It's not that I don't want to reveal my hand, but I do think people who talk about things in advance always end up looking foolish.
The tone, especially on social media, has become more approachable than one might assume when they think of the Times. Was that one of your initiatives?
I definitely think so. One thing I know about working at the Times already is that when The New York Times name and logo is at the top of a webpage, or even a Twitter handle, it carries an outside impact. When we say things, whether it's from the Opinion department or from Styles or the National desk, it's not that we're so important, but it's that it's imbued with this natural authority and that can be dangerous at times if we're not completely cognizant about how we're speaking to people.
Here at Styles, what we talk about when we're writing stories, we say, "Who is supposed to read this story? Who is this audience? Is this story meant to be intelligible by people in Australia and India? And is it meant to be intelligible by young women? Is it meant to be only read by wealthy people who can spend $8,000 on a dress?" Fashion, as you know and as your readers definitely know, is fraught with issues of affordability and audience stuff, and we're trying to be very thoughtful about how we write for people and when we write for them.
I want us to cover high fashion rigorously and intelligently, whether that's from an industry and retail perspective or whether that's from a criticism and fine art perspective, and I also want us to say to people, "Hey, people are wearing this thing on the street." Those aren't the same audiences and/or they're not the same audiences at the same time. The number one struggle in media is we have to begin to address different audiences separately and I think Styles, more than many other places, feels that pressure. Beauty writers know. Beauty writers have to write for people with different skin and different ethnicities and different genders, and that stuff doesn't travel from audience to audience.
How have you seen media change?
I think I caught the tail end of some of the flush years, which was nice. When I started out, I had friends who were like, "I make five dollars a word at Readers' Digest." There was this weird sort of, "No, you can casually make a living as a freelance writer." That's changed, even as it's democratized some — which is also the nice flip side of it — I feel like more people have more access to getting published.
I think we're actually right now on the cusp of something exciting, which is about membership, subscription, people paying their own way for media they want to support. I think we're sort of seeing some of the great dalliances with Facebook and platform publishing coming a little bit to a close. I think that people are saying, "We actually have to stand on our own two feet and defend ourselves," and people want to pay for exciting, important journalism that changes the world or that entertains and amuses. They have shown they are willing to do that and we don't need to depend on giant platform companies always intervening in that.
What do you wish you had known starting out?
I didn't start out until I was a little older, which helps because I think it's tough to be young. I really relate to younger people when they're starting out because I was very anxious. I didn't have a safety net or a support net; I went broke more than once. It's not pretty, and that stress is real and people react to that stress in different ways. I wouldn't have minded it if someone could have looked back from the future and said, "It'll be okay in a couple years. Just wait this patch out." But time doesn't work like that. I could have probably saved myself some ulcers.
Honestly, if I could tell my younger self anything, it would be to get up from your desk and stretch more.
What advice would you give someone looking to follow into your career?
Listen, it's too soon to call my career a success, so I'm not sure anyone should be following me anywhere. Check back in six or 12 months. [Laughs] They have to write big, swinging, career-defining pieces early. If there's any complaint I have about freelancers now, it's that they have been told to make really commodified journalism, so I get a lot of pitches that are very small and very practical because that's what people were paying the money for. You can't make your name by writing stories that are about iterations in shopping or products. People will notice if you come out swinging.
What do you look for in new writers?
I do look for big swings, for sure. I'm interested in people with thoughts that want to address big stuff, but I also like the small stuff. I have a writer I'm working with now; she just had her first piece in the Times recently. It was a fairly local piece, but there were ideas behind it and she is seeing stuff in her world that is not covered by The New York Times. She does not live in New York City; she has not gone to college. She is very smart and observant, and a brilliant writer, and she is pitching me stories about the way we live in the world that I'm not getting anywhere else. That's what I'm looking for, and people should be pitching stories that they are passionate about. Dutiful stories are sad stories.
Everyone here really loves you on Twitter; what is your personal approach to social media?
It's changed a lot over the years. One of the things that's hard for me is I like to be mouthy, but I also don't like and don't have time to get in fights on the internet, so I have to err on the side of not tweeting frequently. [Laughs] And that's good for me and good for the world! But also it's really enjoyable, and not just because when people like things — it feels good and we're trained to appreciate people clicking hearts — but it's nice to meet people online and it's nice to stand for something.
I keep getting pitches from people that are like, "Oh, we should live in a world without social media, you'd be happier." And I don't think I would do take-backs. I remember what it was like before social media and it was kind of boring. I think my only guideline now is I treat Twitter a little bit like I treat the newspaper, which is, I should think twice and maybe have someone else read it before I publish it.
What is your ultimate goal for yourself?
I didn't have very high expectations for myself or a lot of plans, and I have outperformed my meager plans already, so I'm pretty satisfied. And I actually don't find careerism that fulfilling, honestly, at the end of the day. This is a terrific place to work. It's an exciting pile of challenges. The people are amazing and it's fun every day, but it's not going to make me happy. It's not going to make me feel great about myself every morning. It's not going to make my relationship better. That's all still an inside job that I have to do myself.
This interview has been condensed and edited for clarity.