August 12, 2019 -

As told to T. Cole Rachel, 3503 words.

Tags: Writing, Television, Process, Beginnings, Anxiety, Success.

On creating a space for yourself

Writer Ryan O’Connell on how his life became a blog that became a book and then a TV show, the complicated nature of television writing, and why ultimately you always have to carve out a space for yourself and your work.

Often when people ask for professional advice what they really want to know is simply, “How did you get your job?” If you are a writer working in the entertainment industry, this can be a particularly hard question to answer.

Totally. It’s always really unconventional and I always feel bad when people ask me how I got to where I am today. It’s not a one-size-fits-all journey, especially with writing. A lot of it is being there at the right time in the right place and hitting the zeitgeist at the right moment. The difference between things working out and not working out is really often just timing. It’s a little depressing, because it involves things you really, really can’t control, and that’s a little bleak. But in a weird way, it kind of makes you hopeful. It’s all weird. Things add up and things also end up happening not in the way you thought they would, but you kind of realize later on it’s the way that it needed to be, which sounds corny, but it’s true.

Also, I think the most important thing for me to be candid about is that I got some settlement money when I was 18, based on being born with cerebral palsy. My parents sued the hospital. That money gave me a tremendous advantage in my writing career, because I didn’t have to work a day job. I’m a tenacious Virgo from hell, so I wrote every day, all day. I wasn’t sitting at home living, laughing, loving and just being like, “Anyways!” I was very focused about what I wanted to do, but money has given me a tremendous advantage in getting to places I want to go quicker than everybody else.

I think people need to be open and honest about money. I grew up without money and things were very tight around our house. At one point, I literally lived in a walk in closet for five years. With that that settlement, I essentially got to jump a class. We all know that we live in this capitalistic country and things are rigged and the rich get richer and the poor stay poor, but I really, really, really saw that first hand, because that’s sort of what happened to me. None of this was supposed to happen to a boy from Ventura, California. My parents didn’t have money. So, even my getting to live in New York was psychotic, you know what I mean? This wasn’t the way my life was supposed to go, and that settlement money just changed the course of my life forever.

Yes, it’s something people should just be real about. You don’t have to be rich in order to become successful, but it certainly helps. And it makes people really uncomfortable to talk about it.

Yeah, absolutely. How did this young person who has the same job as me end up buying a house? Oh, because their parents give them money. It’s not that complicated. Everyone acts like it’s some giant Nancy Drew mystery, but it’s not [laughs].

Your trajectory as a writer is super interesting—you wrote for the internet and eventually that lead to writing a book about yourself. You wrote for television, which led to writing a television series about yourself, which you then starred in. That’s a wild ride. I can’t think of anyone else who has had quite the same kind of path.

Yeah, it is weird. You’re right, actually. I don’t think anyone else has done it quite this way. I don’t mean to say that in a “Ha, ha! Look at me, bitches!”—it is just a weird career trajectory. Everything happened so fast with me writing for Thought Catalog. That was just such a zeitgeist-y, right time, right place moment. I graduated from college and I wanted to write about the things that I ultimately ended up writing about for Thought Catalog, but there wasn’t a place for the rants and ravings of a stupid 24-year-old boy. I knew there was an audience for the things that I was going through, and I was always really attracted to personal writing. I grew up reading nonfiction. People like Nora Ephron and Cookie Mueller were really, really formative writers for me.

At the time I thought, “Why can’t you just do that online?” Also, the internet was a really snarky place. It was Gawker and nothing else, so I really did feel like there was room, creatively, for earnestness, and also for humor, too. I was writing stuff that was really funny and sometimes didn’t make a lot of sense and was satirical. I just wrote the things that I wanted to see, and I kind of carved out a space for myself. I feel like that’s been my entire career, actually—there never being any space for me, and me just being like, “Okay, well I guess I’ll just do it my fucking self!”

That seems to be a trend now, particularly for comedy people who kept hearing things like: “Oh, you’re too weird,” “You’re too gay,” or “You’re too brown.” So, for a lot of people, it’s like, “All right, I’ll just go and make my own thing and then eventually you’ll want it.”

Totally. There’s a profound lack of imagination amongst the gatekeepers, especially in Hollywood. I live in a town where people start by saying, “We’re not looking for that right now. We want this. We don’t want that.” I just chuckle to myself, as if they ever actually know what the fuck they want. My mind is always like, “Oh, honey. You think you know? You have literally no idea.” This is the diary of a creative person in Hollywood [laughs]. But they don’t know! So I’ve always known not to take that so personally and just know that this is an industry that runs on fear, so when someone says, “We’re not looking for that,” what it really means is, “We tried something sort of like that four years ago and it didn’t work out”. And you’re like, “Okay, well times have changed and also every person’s voice is different, so just stop.”

I know writing a TV series based on yourself, and doing it solely by yourself, is a much different experience than being in a writers’ room on a half-hour sitcom. What was the process like for adapting Special for television?

It was really long and very hard and not fun. I’ll be honest with you. I’m actually very surprised that I pulled it off, and sometimes I think to myself, “How did I even construct an entire season?” I was with these scripts for a long time, honey, and they evolved over time. There were many iterations, there were many different versions of episodes. I would say the second half of the season is pretty unchanged, but the first five episodes went through a million different drafts. Also, I don’t think I ever had a moment where I sat down and I arced out the season, like Homeland style and was like, “Okay, this is what it is.” It was an evolution.

A lot of it was trial and error, and a lot of it was me figuring out how to actually construct this thing. I will admit, structure is not my strong suit as a writer. I think I’m much more of a dialogue queen, and I can write strong characters and strong voices, but developing the structure is not my favorite thing because it’s kind of an equation, you know what I mean? And I could barely pass Algebra 1, so it’s just not my strong suit. However, I will say that writing the whole series by myself and constructing the season by myself really did whip me into shape. It was sort of like writing bootcamp for me.

When you’re making a show like this and speaking so profoundly in a way that no one has ever really done in regards to talking about sexuality and disability, does the weight of representation become a factor? Do you go into it thinking, “I’m just going to tell my story the way I want to tell it,” or do you have to be cognizant of the fact that you are talking about this bigger thing that also affects other people and you need to talk about all of it in the right way?

I definitely felt the burden of representation and I definitely felt nervous. When you’re one of the first people to get a seat at the table, you know that you are under scrutiny, but I also know as a storyteller that you cannot tell everyone’s story. You have to write from a place of truth and authenticity, and the more you do that, in a twist, the more universal your story will become. I truly believe the more specific you are, the more broad-reaching your story actually is. So, while I had that fear and I really wanted to do right by the disabled community, I also wanted them to love the show even though their disability might not look like mine. Still, I also knew that at the end of the day, I could not try to please anyone preemptively or write about an experience that wasn’t mine. I figured that would kind of be a recipe for disaster. So, I just really tried to keep my head down and focus on telling my story and being as honest as possible, knowing that if you always operate from a place of truth and honesty and vulnerability, you’re going to be okay. Maybe that’s not completely true and is a blanket statement, but I have found that to be true in my career.

You’ve written for several different television shows. What actually happens in a writers’ room for a TV show?

Ooh. Well, I think there are two versions of a writers’ room. I think there is the new-school version, which is that there is no hierarchy and everyone has an equal voice, and then there’s the old school version which does mean there’s a hierarchy and it means that if you’re an executive story editor, or a staff writer, you’re considered a “baby writer” and your job really is just to observe and then pitch jokes at the right moment and then disappear.

I’ve been in both kinds of rooms. I prefer the one with no hierarchy because I don’t think a room that runs on fear is conducive to more creativity. I don’t think anyone has felt extraordinarily funny when they feel petrified. I think writers’ rooms are evolving to just being the new-school version, which is that it’s very collaborative. I mean, they’re all dysfunctional, don’t get it twisted. They all have their own quirks and their own dynamics, but I’ve been very lucky to be in some incredible writers’ rooms, especially with Awkward. That was my first job and I was on it for two seasons. Everyone in the writers’ room was pretty young and for most of us it was our first job, so we kind of all came up together and became sort of like a family, legitimately. To this day, those people are some of my closest friends and that’s not the case with every job.

It’s interesting. The writers’ room provides a kind of forced intimacy. You get really close with people for like, six months and then you literally just never see them again. It’s really weird! It kind of suits me in a weird way because I like connecting with people and being thrown into weird environments and then figuring it out. So it suits me, but it is definitely a strange way to make a living, absolutely.

What do you tell people who want to know how to get into the business, or how to become a writer for television?

Honey, I tremble with fear and I search for an “Exit” sign because I literally don’t know. My getting on Awkward is a story that I have to tell behind bulletproof glass because it never happens, ever. It’s definitely a one-in-a-million thing where I moved to L.A. and I got representation from my book agent because I wrote a pilot, so I was repped by U.T.A. I didn’t know anything about the business. I’d never been in a meeting before. I came at the wrong time, so I missed the period where most places are staffing. My agent was like, “Oh well, what shows do you watch?” and I said I really liked that show Awkward, and coincidentally it just so happened to be staffing literally at that moment, and so my script was sent over and I met with the showrunners and I got a job within four weeks of living here! Again, this does not happen, I didn’t know how hard it was. I was just like, “Oh! You go to a meeting and you get a job!” But the reality is that people work for years; they work for years with a script coordinator, they work for years as an assistant. There are lots of different and difficult points of entry.

And how difficult was it to get someone to give the green light to Special?

Well, when we initially pitched Special as a TV show it was in 2015 and no one bought it, which was devastating because the pitches went over so well. We left every pitch being like, “They’re going to give me an offer!” …and no one did. I was so upset. I mean, looking back, it was the right time, right place thing—you have to wait for the culture to catch up. I don’t think the culture was there yet in terms of highlighting a gay disabled story. I thought for a long time that it was just never gonna happen, that it was gonna die in development, but it didn’t. In a way, I’m super grateful because I think that if it had sold in 2015, the chances of it actually just dying after the script phase would have been so high. It can go wrong in so many ways. You sell something, woohoo!, and then you write the pilot and they’re like, “No, we don’t want this,” or you actually shoot the pilot and they’re still like, “No, we don’t want this.” There are so many steps. I think having the time to develop the season and write those scripts over the course of a year and really own them was so important. We eventually sent them to Netflix, who read all the scripts, understood exactly what the show was about, and ordered it straight to series. That was a blessing. It really was. Because again, if it had sold before, I would say 99.9% chance that it would’ve just died completely.

You also had the experience of working on Will & Grace. How do you think shows like that have changed the way people think about and relate to gay people? Or have changed the way we are represented in the culture now?

I have a lot of thoughts about gay representation on TV because I think that in a lot of ways, TV is gayer than it’s ever been. Absolutely. There’s no denying that. But I really, really implore you to think about how many shows there are on the air that have just a gay male lead story. Like, it’s just a gay man’s journey. There are none. I can think of Please Like Me, which didn’t even air in the U.S., it aired in Australia, and Looking, which was canceled after two seasons, and that’s sort of it? Like, I know we’re getting a new Tales of the City on Netflix which is great, but it’s like… </span>on television gay men can exist, but they are never given the flexibility to be the main course.</span> They are always the fun flirty appetizer, they are always there to add texture to the main person’s story, so I think we still have a long way to go.

Ryan O’Connell Recommends:

So, this is going to sound really cheesy but Best Coast’s Crazy for You is an album that I’ve had on repeat for the last 10 years because it’s so dreamy and summery and wistful and I just think it has like this magical purity to it. It never fails to make me happy. Never ever! I also think at heart I’m like a 23-year-old longing for some emotionally unavailable bro, even though I’ve had a boyfriend for four and a half years and everything’s great. I think I just spiritually identify with this record all the time.

As for writers, I love Cookie Mueller. Her writing never fails to cheer me up or make me think about life in some new and interesting way. Another book that I always try to keep near to me is Self-Help* by Lorrie Moore, which I think changed the course of my life forever. I didn’t know how to write, but I did know I had a tiny sprinkle of a voice, and I remember reading *Self-Help, which is all second person, and when I started Thought Catalog, all my posts were in second person. This was because I didn’t know how to write (laughs) and writing in the second person is actually incredibly easy, and you can actually get very emotional and achieve a lot of depth without knowing how to actually construct sentences together. Reading Self Help was revelatory for me. It was sort of my own guide to how to write a book. I love that.

Oh, the Olsen twins! The Olsen twins were always my spiritual guides, I can fall down a Tumblr k-hole with them whenever, wherever. I think they’re psychotic and I love them. I actually think Mary Kate is getting plastic surgery to make herself look older, which has never been done, but leave it to them, those iconic twins, to really be on the cutting edge of everything. Here’s the thing. They’ve been famous since they were only a few months old, so they didn’t stand a chance. They were going to be forever weird no matter what. When I was acting in Special, I suddenly had this newfound empathy for actors because they’re all weird, and they’re all weird in the same way, which is that they need attention, they’re a bottomless pit of need, and their whole self-worth has been placed into other peoples’ hands since the moment they started acting. All of that is going to fuck you up psychologically. So you look at the Olsen twins and you’re like, you know what? All things considered, they turned out okay [laughs]. They run an empire and they’re so chic. I love them.

I have to recommend Seek Treatment, this podcast by Cat Cohen and Pat Regan. I’m like an alt-comedy bitch from hell and my boyfriend LOL’s at me because he’s like, “All you want is the acceptance from the alt comedy community”—people like Patti Harrison, Mitra Jouhari, John Early, Kate Berlant. I just love all of them and they scare the hell out of me because they’re so brilliant. I never listened to podcasts before Seek Treatment and I think they are truly two of the funniest humans to ever exist. They’re also not political at all, all they do is talk about their crushes [laughs] and I think in the heavy negative state of the world that we live in now, there’s something so refreshing and subversive about just doing a podcast where you talk about boys and sex. It’s like you don’t live in Trumpland, you just live in Forever Boy-land. I think it’s such a delight and it’s amazing escapism and everyone needs to listen to it.

I’ve been going on the swing set since I was a little kid, and I still go on the swings at least once a week, which is unhinged. I’m a 32-year-old gay male and I have no business just going to the park to swing, but it is seriously where I get all my ideas. I put on my headphones and I go on the swings. I can swing up to two hours, I’m not kidding you. I will walk away with blood blisters on my hands. I stay on those swings fucking forever. I blast my shoegaze and I swear to god, it is a transcendent activity. It’s just my safe place, my euphoria, so I highly recommend the swing sets. I’m saying that partially out of selfishness and not wanting to not look like the only psycho old man at the swings who’s literally just listening to my music, trying to get my creative mojo, and not there to try to leer at kids.