on the wonderful problem of making theater

What is it about your own psychology that makes you well-suited to writing plays? Why is theater the best mode of expression for you?

I was originally drawn to poetry. I think that plays are closer to poems than they are to films or novels. I also just love the fact that, when writing a play, you’re sort of desperately lonely and trapped and dealing with this idea on your own and then eventually—hopefully—you’re really collaborating in a very intense way with actors and directors. There is something about making a play that requires you to approach a problem from completely opposing angles that I have always been drawn to as a kind of introvert/extrovert—someone who is afraid of being alone but also is terrified of being around people for too long.

The other thing is that I came at play writing through a love of plays. I acted in plays when I was growing up and I always loved that feeling of “Hey! Come on! We’re putting on a show for our friends!” The other thing is that, when I was younger, I was a pretty slow reader. It took me a little while to feel excited and confident about reading long things, but I also loved literature and loved language and there was something about plays that was appealing to me. I could get into reading plays.

After I went to college and studied different kinds of writing, I eventually became a serious reader, but I was always drawn back to theater. Sometimes I still ask myself, Why do I write plays? Why this? I think I just love the weird problems it presents. It begins as something that is totally ineffable and then it becomes more and more practical—there are all these problems to solve—the further you go into the process. It’s about things like, “Oh god, we have to make a mirror in this scene look like that? But we also can’t break it, so what are we going to do? Or, this character needs to change clothes between this and this scene, but how do we have time for them to do that?” Theater presents all of the wonderful, maddening problems that you have to somehow work your way around.

So it’s this great thing where one’s poetic ideals, or even just emotional sense of what a thing is supposed to be, eventually has to crash into the brick and mortar reality of trying to make a thing using 3D objects and actual people in time and space. You never get the thing you start out chasing. The thing in your head disappears and it becomes this other thing.

What is a play in its most perfect version? Is it the play in performance? Is it the written version of the play? Or is it some imagined version of what it could be?

It’s all those things… and there’s something comforting about knowing that. With a play, the document survives all of the things that happen to it. And that doesn’t mean anyone cares about it or anyone reads it, but the document survives and it survives its reviews, it survives its production and it continues to exist as this thing that could be brought to life in theory at any moment. There’s something there that gives the play on the page a certain power, because its just pages of potential. It would require a lot of people giving over their entire lives to it for it to happen in any way, but there’s also something about that aspect of it that’s appealing.

Do you have a particular way of working? Are you always working on something new?

I’d say I’m stuck about 85% of the time. I really do actively avoid writing in incredibly elaborate ways. It’s like I sort of just play chicken with myself for as long as possible before I finally have to sit down and write. I have tried to not do that—and I sometimes succeeded in not doing that—but I’ve also come to accept that this is just how I work and that’s how I make plays. In a way, I feel like there’s always something that I am approaching and avoiding. And if I’m really avoiding it that means I’m pretty close to actually doing it.

I wrote this most recent play, The Treasurer, late at night, between the hours of one and five in the morning. I was in school in Julliard when I was writing it and there was something about feeling like I was the only person awake that created a sense of privacy around what I was doing. I think that was useful to me and definitely to the play.

I’m always looking for that—a way into working on something. Now I’m getting a little bit older and I don’t want to stay up all night, every night, in order to write a play. It’s interesting trying to trick myself into feeling that same kind of privacy in broad daylight when everyone else is also awake and emailing you. I have started writing some things out in longhand more than I did before, just because I think it makes you feel closer to the process of active writing, which is something that is harder and harder to get at. It feels more direct to be actually doing something slightly more physical. We are all just constantly typing, typing, typing and using our thumbs to form sentences and words that often have nothing to do with really using our minds. It’s nice to have something to mark the difference between living and writing.

So it’s a constant dance. I personally feel like pressure is helpful and so I have to construct deadlines for myself as I’m not in school and I don’t have the same sort of institutional obligations to things like writers groups, which is something I had for four or five years as a student. I have to really trick myself into feeling like something bad will happen unless I don’t do something by a certain day. And I have to really believe that somehow.

Lots of writers I know have those sorts of things—these self-imposed deadlines and restrictions, complicated mental gymnastics that are required in order to trick themselves into writing something or finishing something. It’s different for everybody.

And its different for every play, too. Some plays require you to be a certain kind of person while you’re writing them. You have to create this certain kind of space around it and you know when you’re entering that space that’s the mind that you’re living in. For me, it has changed from play to play, what that space actually is, so in some ways the avoidance is just waiting to find the right channel.

There is a unresolvedness in your plays, an avoidance of narrative tropes. I’m thinking particularly of The Treasurer, which suggests that no one is truly good or bad and even terrible people can be endearing. Theater seems to be one of the few creative spaces left that is willing to explore that. It happens less in the movies.

I’m interested in plays where the experience isn’t unanimous, where people are finding different things funny and are maybe mad at the same things that other people are finding funny. I’m interested in making theater complicated because generally there’s this responsibility and urge to entertain everyone. I think there is a simple version of entertainment where it means that the intention is unanimous and we all sort of agree about how this thing is making us feel in any given moment or what it’s doing to us. I’m really excited about trying to find a way to do the opposite: to gather people together and then divide them up meaningfully in terms or their reaction.

Plays, much like films, can live or die according to casting or even who is working behind the scenes. It’s like an elaborate puzzle where if even one piece is wrong, the whole thing can easily collapse.

Yes, completely and that’s what’s so scary about it. That’s also what’s so great and also so impossible about the fight of living as a playwright in New York City under the conditions that I’ve been living in. It’s like… Ok, you want your play to happen, but you also want to do everything in your power to avoid this feeling of gambling, that you’re rolling the dice to see who can do your play and if they are right for it. With The Treasurer I had been working with certain actors in mind for over a year. I have not felt this in every play I’ve done, but this time I really wanted to feel like by the time we started rehearsals I wasn’t imagining any other people in these parts, I wasn’t thinking about anyone outside the room.

I was really writing towards these actors and their voices, which is something that I like to do. We were lucky, but there were actually a couple of crazy things that happened along the way. Peter Friedman, who plays the son in the play, got an HBO show and so we had to move the play around for him, but then it meant it overlapped with the production of Hamlet that he was doing. And then David Cromer, the director, had a Broadway musical that was announced as coming two months before they thought it was going to, which meant that it would fall directly during our process, so we had to rearrange the entire schedule, which also meant that Peter was doing Hamlet during our entire rehearsal process. He had one night off after he closed Hamlet and then he had our first preview with a paying audience.

So there were these crazy stressful moments where I felt like “Oh god, is it all going to fall apart? Can I retain my loyalty to all of these people?” I felt so monogamous towards every person working on it. I prioritize people over time or schedule or even process because I ultimately felt like, if you don’t have the people that really make this thing with their DNA, you can’t do it. No amount of rehearsal time makes up for that.

For aspiring playwrights, people that are just entering into to this world, what advice do you have?

The most important thing is to continue to share your play and to let that teach you what to do next and how to do it. That can be as simple as just gathering people that you know around to read it out loud. Institutional support is obviously helpful and important and maybe even crucial at certain points, but I think that none of that comes without you—sort of against all logic—deciding that you are a playwright, which is a completely irrational thing to decide because you have no evidence of it at the beginning. You almost need to declare it to yourself and make that decision before forging ahead. For me, I surrounded myself with people that I felt understood this very particular kind of tonal conversion that I am hoping to find in my plays. I just kept those people close to me.

The other thing is, if you live in New York city, or you move to New York city, which is what I did, there are organizations who basically take it as their sole responsibility to find the next playwrights. Page 73 is an organization that actually produced my first off Broadway play. You have to be a playwright who has never had a New York production before. They have an open submission process and you send them a sample. I ended up joining their writers group and then they gave me this fellowship not that long after I moved to New York. That really did change my life, because even though I was working a day job and most of my hours were not spent feeling like a playwright, it changed my perception of myself. That is probably when I started writing through the night because that was the only time I had. As with anything, you have to go out and find your people… and you have to go out and find the people who might be out there looking for you.

If you are in New York—or anywhere where there are plays—you have to go to them. You have to be someone who wants to spend your life watching things on stage, which is a crazy thing to do and a crazy thing to want. And it is frustrating and disappointing most of the time, but for some reason you have to just want to keep going because every now and then something miraculous happens. And then you make these funny connections and have these little revelations. You see something and say, “Oh my god, that actor!” which is what happened when I first saw Peter Friedman in a play, which was about 10 years ago. Now he’s in my play. You start to know and understand the actual humans who make up this world. Eventually these people become your friends. Eventually this world becomes a place where you all reside.