Is Ryan O'Connell the Real First Voice Of Our Generation?

Whatever else might be said of millennials, no one can ever fault us for not having enough thoughts. When it comes to critical analyses of Snapchats or extended meditations on the drudgery of unpaid internships, we have an embarrassment of riches. We’re a generation of over-thinkers, of Hannah Horvaths philosophizing in our underwear, Costco-grade container of Cool Whip in hand.

But, until a few years ago, the fruits of our over-exertive thinking were limited to brilliant Facebook statuses and memorable late-night dorm-room roundtables. There was little out there, in the world of writing at least, to reflect and make sense of our generational sensibility.

Thought Catalog (TC), when it debuted in 2010, was one of the first websites (if not the first) to give serious attention to the stuff of the millennial mind, and it did so in a way that felt millennial. Before it became the wildly popular destination it is today, TC was a small, largely submission-based operation with only one full-time staff writer, but that writer turned out to be the bread and butter of the site’s success.

Ryan O’Connell, a then-24-year-old New School graduate, wrote about relationships, sex, depression, and being gay in a voice that was at once endearing, lewd, and schoolmarmishly wise. Responsible for some of Thought Catalog’s early viral success (“How to Be a 20-Something,” “What It Feels Like to Get F***ed in the Ass”), O'Connell's unique way of writing about the triumphs and pitfalls of millennial life became a genre unto itself. There was no 20-something situation, observation, or feeling that couldn’t be condensed into a 300-word essay or 5-item listicle. TC posts, recognizable by their candid, click-or-die headlines, began spreading on Twitter and Facebook like wildfire.

Thought Catalog has grown up a lot in the last three years. According to editorial director Brandon Gorrell, the site draws some six million unique visitors every month. It's also become a launchpad for millennial-generation talent, helping to fuel the success of writers such as Tao Lin, Marie Calloway, and Sarah Nicole Prickett.

O’Connell has done some growing up, too. While he still writes regularly for TC, he’s also published three long-form essays as e-books with Thought Catalog Books and is currently at work on his first full-length book, I’m Special. I recently talked with O’Connell about the early days of TC, the regrets he has about some of his early articles, what his next career step will be, and why writing a book sucks.

Daniel Lefferts (DL): How did you come to start writing for Thought Catalog? 

Ryan O'Connell (RO): I graduated right when I turned 23, so there was a solid year of me interning my face off. I wasn’t really sure of what I wanted to do. I had been submitting stuff to various websites and they all were like, “This is good, but it doesn’t really fit our editorial.” Which was true, it didn’t. Thought Catalog at the time had just started. It was a very open place where any kind of submission was welcome. So, I saw this opportunity to be creative without any kind of restraints. I submitted the stuff I had been working on and I was fortunate enough to have the readers like it. That eventually led to a full-time position.

DL: What was that year before TC like?

RO: I was really scared. The stuff I’d written in college was terrible. I knew that I wanted to be a writer and all I loved to do was write, but I hadn’t really found my voice yet. In college, you’re reading the classics — lots of Didion and Bukowski — and you have this kind of fixed idea of what writing can be. And I thought, OK, I have to write like them. If I’m gonna be a writer with a capital W I have to write about like, desert roads. And I did and I was terrible at it. I over-thought everything. 

I’ll never forget the first piece I wrote for Thought Catalog. It was called “How You Speak to Your Ex-Boyfriend vs. How You Want to Speak to Your Ex-Boyfriend.” It was something that had happened to me [and] I went home and just wrote it. And I was like, Oh, I can write about this! I can do writing that’s like this, and do it in my voice. I think the second I did that, something clicked for me. I mean, I was still a horrible writer. I couldn’t string sentences together. But at least I knew what direction I wanted to go in.

DL: You wrote a lot for TC, especially at the beginning. Sometimes three or four posts a day.

RO: I wrote a lot. And that’s what happens when you’re 23 or 24 and you’re hungry and you have so much to say. Honestly, no one was writing about this stuff on the internet. Maybe that sounds pompous or whatever. But, really, [no one was writing about] the most mundane things. About literally having a conniption fit when somebody doesn’t text you back. This was before Girls, this was before the New York Times jacking itself off about 20-somethings every weekend. This was before millennials became millennials. Everything was so ripe. So, for the first two years, oh my God, I was a Tasmanian devil. Which was great. I liken writing for a blog to going through writing camp. You write so much every single day. It makes you so disciplined. And it allows you to be able to come up with ideas instantly. That’s really valuable as a writer. A lot of writers don’t write. It’s difficult for them. At Thought Catalog, there wasn’t an option to have writer’s block. It was really the best kind of training I could have as a writer.

DL: Has your attitude toward writing changed as you’ve gotten older?

RO: I definitely feel more careful and thoughtful in what I write. Before, I had no standards at all. I would just write and see what happened. I kind of cringe when I look back at things I wrote in 2011 glorifying drug use and being insane. “It’s fun being a psycho!” I kind of learned that it’s not fun to be a psycho, and that everything you do has consequences, even when you don’t realize it. You can’t really go through life being a raw nerve all the time. When I started at Thought Catalog, I felt this obligation to experience it all, and I experienced too much and it hurt me. So, I don’t relate to some of the stuff I used to write. I’ve definitely kind of wised up in that department. But you know, also, being a mess was super-inspiring. I wrote a lot. It was a really interesting time; it was a really fun time. But it also feels good to close that chapter and start over a little bit.

DL: You’re working on a book, I’m Special. Can you talk a little bit about it?

RO: I got the book deal about a year and four months ago. So I’ve been writing it for a long fucking time. It’s been a fucking experience. Basically, it’s part personal narrative [while also] talking about all facets of millennial life. I have a chapter about internships called “The Devil Wears Urban Outfitters.” I have a chapter about online dating and how dating has changed. And I also have some stuff from when I was growing up and all the weird shit that I experienced. It’s a little bit of everything.

DL: What are the big differences between writing for the Web and writing a book?

RO: So fucking many. It’s harder to write a book, without a doubt. Blogs are just, oh, I have a thought. With a book you’re constantly [thinking big picture, asking yourself] does this fit here, does that fit here? It all has to be connected. And I don’t write like that! I’ve been writing for the Web for three years. It’s taken a lot for me to switch gears.

DL: Are you a little tired of it?

RO: [Laughs.] You’re catching me in a moment. I think if you sit with a piece of writing for over a year, yeah, you’re gonna get tired of it. You’re gonna get fucking sick of it. Everything you write is gonna seem horrible. You don’t have distance from your material. There are days when I wake up and I’m like, “Oh my god, I fucking hate this book. This book sucks.” And then I’ll just work on it, get it fucking done. Then I’ll wake up the next day and read it again and I’ll be like, “Oh, this is actually kind of good.” It depends on the day, honestly. When it’s done, I’ll feel so happy that I did it and I’ll be so proud of the finished product.

DL: Do you see yourself writing more books?

RO: No! Fuck no. No more books. This is the last one. I’m hoping to get into TV writing.

DL: Which TV shows would you would like to write for?

RO: I don’t want to say, I don’t want to jinx anything. I might be having meetings with them. I’d be happy to write for anything. LOGO, Lifetime, BET, you name it.

DL: If you weren’t a writer, what would you be?

RO: I’d be a therapist. I just love understanding human behavior and why people do the things they do. The only thing that actually scared me away from pursuing psychology was the math (statistics).

DL: Do you have any favorite Thought Catalog articles that you’ve written?

RO: “How to Die on New Year’s Eve.” “How to Be a 20-Something,” just because it really took off and became the first viral thing I had written. I like “The Stupid Things We Hold Onto.” I like basically anything that’s super-super-funny or super-super-depressing.

DL: Who are some 20-something writers that people may not have heard of but should read? 

RO: I like Mitchell Sunderland. I think he’s gonna have a major career because he’s literally going into his senior year at Sarah Lawrence and he’s already an editor at VICE. Stephanie Georgopulos, who wrote for Thought Catalog and is now at Gawker. I love Brandon Gorrell. Sarah Nicole Prickett. She’s my fucking favorite. She writes things like that literally feel like someone just fed me a giant Adderall. You just want to reread [her stuff] over and over again. I like writing that makes me feel like I’m getting an electric shock.

DL: What are some good books you’ve read recently? 

RO: I just read Choire Sicha’s Very Recent History. Super addictive. There’s also this book called The Flamethrowers by Rachel Kushner and it’s amazing. Taipei, by Tao Lin, which is great. I live with one of the co-creators of the Twitter White Girl Problems. They just wrote a new book. It’s phenomenal. I can’t wait till that comes out. 

For more writing by Ryan O'Connell check out his profile on Thought Catalog.