Ryan O’Connell on Thought Catalog, trolling & the Millennial angst tipping point: "The more you write about your personal life, the less you have one”

The former Thought Catalog star tells Salon about his new book, "I'm Special: And Other Lies We Tell Ourselves"

Published May 23, 2015 11:00PM (EDT)

  (Sarah Walker)
(Sarah Walker)

When Ryan O’Connell started writing for Thought Catalog in 2011, I was a 20-year-old girl with a lot of feelings and even more uncertainty. O’Connell was a few years older than me and living in New York, a complete stranger who updated his roadmap to Millennial angst – published in the form of listicles and second-person confessional essays – daily on the nascent site. I was so, so good at following it, even when I wasn't reading it.

Given the earnestness of this interview intro, it’s probably clear that I can still be very good at the Millennial angst thing; for this, I suppose I owe a debt to O’Connell, who quickly became known for his insight on “How to Be a 20-Something.” Personally, I was bad at some of what he listed as crucial -- the binge-drinking and drug use, for example, for which I’m now grateful -- but very successful at having hip wannabe-filmmaker friends who read Tao Lin and hosted punk shows in their dank Austin living rooms.

My friends would occasionally contribute to Thought Catalog, then a burgeoning, somewhat highbrow platform where they could submit things like snarky reviews of Mormon.org or lists of experimental musicians’ Facebook pages. The site had not yet become the trolling behemoth it’s now known to be, but was, as Newsweek recently noted, criticized for a different reason: essentially, O’Connell’s sincerity.

He was the star. He would reckon with the meaning of his 20-something existence before a growing Internet audience and get all the clicks, because people like me were eating that shit up.

O’Connell made his name by churning out hundreds upon hundreds of how-to guides and justifications for bad behavior – “How to Fall In Love With a Boy for the First Time,” “How to Appear Cooler On Facebook than You Really Are,” “Why It’s Okay to Flake on People Sometimes” – which simultaneously made him untouchable to other, more mainstream media organizations. And yet you might have noticed that the sort of somber indulgence in nostalgia, anxiety and desire for which O’Connell became known – which became the O’Connell brand – is everywhere now. Just take a look around at your Internet.

That’s not what O’Connell does anymore, but it sort of is. After using Thought Catalog as a launch pad -- and paving the way for other 20-somethings to pour their hearts out online in some effort at human connection -- O’Connell branched out, writing essays for Vice and eventually getting a book deal. His first manuscript was also about “how to be a 20-something,” and was, he told me recently, terrible.

“It wasn't easy,” O’Connell said of the essay collection when I spoke to him by phone earlier this month. “The first draft I wrote of the book was such garbage. It was so bad.”

So he left the full-time Internet writing game, moved to Los Angeles, and came up with a different idea: an essay collection that’s still about being a 20-something, but is infused with a general indictment of the entire online culture O’Connell has, in a way, been instrumental in creating.

The book, “I’m Special: And Other Lies We Tell Ourselves,” is a grown-up version of the type of writing for which O’Connell is best known. It is deeply revealing in the most casual manner, and deals with topics O'Connell chose not to touch at Thought Catalog -- specifically, what it's been like for him to live with cerebral palsy. The book still preaches to the aimless-ish Millennial, leans heavily on Internet slang and is meant, clearly, to be relatable. For the most part, it is – at least to me, a white 23-year-old who grew up affluent, lives in New York, writes for the Internet and read Thought Catalog back in the day. I also still have a lot of feelings and plenty of uncertainty, so I'm pretty much the target demographic.

And that’s sort of the problem: The book is part of a genre that is meant to appeal to the universality of 20-something angst, but relies overwhelmingly on experiences that aren’t universal. Rather, they're unique to a very narrow, privileged demographic. It’s an issue O’Connell actively tries to address in “I’m Special,” with a discussion of the role socioeconomic status contributes to “the Millennial experience” – if such a term can even be applied to the myriad realities of being a 20-something. He's aware of the problem, and of the ubiquity of the problem and of the way places like Thought Catalog contribute to it. But that doesn't mean he's going to stop writing.

O’Connell spoke with Salon by phone about his new book, which comes out June 2, as well as how he feels about Thought Catalog’s turn toward transphobic trolling, what he has to say to critics of his writing, and what he’s looking forward to as he wraps up his 20s. Our conversation has been condensed and lightly edited for clarity.

How do you go from already having put so much of your life on the Internet in blog posts to writing a book? I feel like you sort of pioneered this certain kind of blogging that is now ubiquitous and then you went old-school and wrote a book...

Yeah, it was a vintage moment, it was a throwback Thursday!

How did you navigate that?

At first, it was really difficult. I got this book deal when I was 25, and I was working full-time at Thought Catalog still. The book that I sold to Simon & Schuster was kind of bad. I think it was literally called "How to Be a 20-Something" — it was terrible, but God bless them, they bought it. So when I got the book deal I realized I didn't want to write about that, and I knew that if I really did want to write a book, I had to make it different. I wanted to write about my disability, which was something I had never talked about before. Well, actually, my editor was like, “I think I have a title for your book. I think we should call it, ‘I'm Special,’” and I was like, “Funny you should say that. Not only am I a special snowflake, but I'm riding-the-short-bus special as well.”

You said this is the first time you wanted to write about your disability. Do you feel like now you’ve used up all of your personal material?

No... It's interesting, because this book to me really represents the end of that chapter of confessional writing. I'll always be writing personal essays, but not that much. To me, the next step in my writing is just writing for other shows, creating my own show, and just immersing myself in that world. My life just isn't that interesting anymore! It's a good life, I'm happy, everything is relatively stable. When I was writing for Thought Catalog, I was a hot fucking mess. I was on drugs, I had shitty friends and I was pretty miserable, which obviously inspires good writing, but for mental health isn't so good. Once you find your life taking a more stable shape, what are you going to write about?

I'm curious how you know which mundane aspects of your life are actually not that mundane, and are worth exploring. Or did you just kind of think everything was important when you were writing for Thought Catalog?

If I feel drawn to something enough to actually sit down and write about it, I usually know I'm onto something. Writing is such a painful, horrible process that actually wanting to sit down and make a point of writing down your thoughts -- that means you're onto something for sure.

Right? Why do people always think writers actually enjoy writing?

That's the thing: When you do it, it should count. When I look back at my old stuff on Thought Catalog, there was no filter; it was definitely quantity over quality. Now I feel like I'm much, much more choosy about what I want to put out. When I write things for Thought Catalog now, I feel like it needs to add something to what I've already discussed. I always see universal things in specific things I talk about.

You talk a little bit about socioeconomic class and background, but what do you make of critiques that your writing is speaking to a very distinct class or racial group -- that a lot of what might be your personal experience isn't really that universal, and that it overlooks the experiences of other Millennials?

Everything does, though. That's culture, that's movies, that's TV shows. You always write what you know; at least I do. I would never try to speak for things I've never experienced. I would never even try to put myself in a position where I'd comment on something that's way out of my league. Here's the thing: Things always look different on the surface. I think that on the surface, everything looks different -- class, race, whatever -- and that definitely informs your existence, but when you strip everything down, wanting human connection and wanting to be loved is universal. Wanting to feel not alone is universal. What I hope my writing tries to get at are those basic feelings that I think everyone experiences in their 20s or forever. I may not always succeed, and it may be more specific than I think, but I do try to get to a larger picture than just this privileged 20-something angst.

Speaking of privileged 20-something angst: The book is called "I'm Special," and the whole opening part is almost an indictment of “special-snowflake culture.” But you are special! You did do it! You did the Internet and then you got a book deal and started writing for TV. How do you grapple with that?

I mean, it's funny: I think there's two different kinds of special. I think the specialness I hate and what gives our generation a bad name is feeling like you're entitled to things and to really only see yourself -- that narcissism that is toxic and prevents you from seeing other people's perspectives. I think that does happen in our 20s, for sure. I'm definitely throwing shade at the special-snowflake thing, because I do think that's a toxic way to live. I think being special is living your life as honestly and authentically as you can, and being open to other people's experiences, being generous, being kind.

There was one part of the book that struck me -- you say "I was good at this, prefacing something humiliating and painful and turning it into everyone else's pleasure” -- and I think that's what really defined early Thought Catalog and your work there. As someone with a lot of feelings, and who was so involved in developing the site, how do you feel about it now?

It's complicado... In one way, Thought Catalog will always be my family. I write for them still sometimes and it feels good to be there, and I feel like I have a lot of readers who grew up with me and who -- for lack of a better term -- have followed me on my journey. But, you know, the editorial has changed; they've definitely become a lot more open in terms of what they publish; it's now become a place where anyone can have a voice; it's not so curated anymore. I don't agree with everything they're doing, obviously, and it's no longer the website I was really involved with. But at the same time, you do you, babe! God bless.

Do you think all thinking is actually relevant? I'm referring to the fact that there has been some really transphobic, gross stuff published on Thought Catalog.

Trust me, Thought Catalog is not sitting there being like, “Let’s do that again!” The thing is, when you have a huge website like Thought Catalog — and by the way, their staff is not huge, and they're publishing 10,000 pieces a goddamn day — there's going to be some pieces that fall through the cracks and that make people smack their foreheads. I wasn't there so I feel weird speaking for them, but I definitely think that that happened and it was like “Oh my god, we need to monitor this stuff better.” Thinking is relevant as long as it's not hate speech, to me. Hate speech is hate speech; that's just what it is, and that is not relevant. I think they would agree, but honestly they just fucked up. Websites fuck up all the time and publish things they shouldn't have, and then they learn from it and grow and don't do it again.

How do you determine what to share about yourself and what to keep private? It sounds like hiding your disability was actually toxic —

Oh, yeah. It was bad for me.

Right, but I imagine that it might have felt almost like a form of self-preservation.

There was a certain vibe that Thought Catalog readers didn't fucking deserve me talking about my disability. I was so damaged at that point; I was so closeted about my disability that I blocked it out of my brain. For something like my disability, I just knew I needed to take the time to explore it and to delve into it. I think in the beginning I made a few missteps with writing, where I would just write about whatever and I didn't care. But if you piss enough people off, you learn to have boundaries as a writer. I think, again, that's something you develop as you get older, the longer you've been a professional writer. You just have a good sense of what's worth sharing and what's not. I definitely was a psycho in the beginning, just writing my life away, but that impacted my personal relationships. The more you write about your personal life, the less you have one. I'm more interested in having a personal life than in writing about one now, but that's something I had to find myself.

Do you feel like you're the voice of a generation? Or at least a voice of a generation?

Oh god. Babe, I cannot.... [laughs] I mean, no. Just no, no, no. Uh-uh. When I started writing for Thought Catalog, I will say that no one was really writing about our generation, not yet. I know that seems crazy because a lot has changed in four years, and when someone writes something about the 20-somethings you're like, “Oh my god, fucking kill me.” It is tired. But this was before “Girls,” and I think there was literally one op-ed in the New York Times called "What is it about the 20-somethings?" that had gone viral. That was the first time I remember seeing the Millennials be talked about, and then I wrote "How to be a 20-something" shortly thereafter. It sounds stupid, but the stuff we were writing in Thought Catalog in 2010 and 2011 felt very trailblazing, and I think we had tapped into the zeitgeist and were doing something kind of special. Nobody was talking about it. Now it's hilarious because that's all people do, this personal writing.

Do you think it's bad how ubiquitous that is now?

Here's what I'll say: I think we're oversaturated for sure, and when I think of special strong voices I think of people like Cat Marnell, those writers like Marie Calloway. What I do see a lot today that annoys me — I sound like a grandfather of the Internet shaking his cane at the young people today — I see people adopting this same-y bloggy voice, this kind of affected, quirky, weird, jokey voice that doesn't feel like themselves. I feel like it all reads the same to me. It's really rare that you read a writer nowadays and see a very specific voice. I think something needs to change; maybe a new topic will come up. I think people are just fatigued right now, you know?

What do you want people to ask you about the book?

The one thing I would say is that no matter how much of a mess I was in my 20s, I was laser-focused and I was very hardworking. Listen, I was doing drugs and going crazy and being irresponsible, but I also always kind of knew what I wanted to do and that carried me through. My work never suffered; I never let it because that was the one things that made me feel sane.

It's interesting that you say that. I feel like for so many successful creative people in what we now consider “Millennial entertainment,” so much of their work portrays their characters’ misguided laziness and aimlessness when, in reality, the people who are creating these things —

Oh my god, they're the hardest-working people. Yep. In order to do that -- in order to get “Broad City” made, in order to get “Girls” made -- you have to be so hardworking, so determined. I think people feel like ambition is a dirty word, you know what I mean? Knowing what you've always wanted to do is something we're supposed to be ashamed of. The fact is, I had a five-year plan when I started working for Thought Catalog. But it's true that I created this image of myself as someone who didn't have their shit together, and in a lot of ways I didn't -- I really was falling apart. But I also think there's a separation between your work and what you're going through in your personal life. My work was always a separate thing, and I was really protective over my work and my drive. To me, that was the one sacred thing, the one thing that I had that I couldn't let go of no matter how bad things got. I think it's really, really, really important -- especially when everything around you feels like it's turning into shit -- to always be working toward something.

By Jenny Kutner

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20-somethings Books Editor's Picks Essays Millennials Personal Essays Ryan O'connell Thought Catalog