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Effective with Charlie O'Leary

54m 19s

Effective with Charlie O'Leary

Charlie O'Leary’s play *Effective* is a dark, satirical exploration of toxic workplace culture, inspired by his own experiences working in corporate environments and witnessing the rise of authoritarian leadership—particularly Elon Musk’s takeover of Twitter. The play blends naturalistic dialogue with abrupt theatricality and absurd moments to depict the emotional and psychological toll of a system that values performance over well-being. Initially written from a cynical perspective, O'Leary reworked the play to prioritize character empathy, showing that even in its most violent ending—where characters kill their manager—the human desire to resist and survive remains central. The play reflects on whether modern work is worth the cost, questioning whether capitalism is a necessary path or a form of emotional and physical destruction. While it ends in chaos and ambiguity, there's a quiet hope in the final lines, where the characters acknowledge their deep care for one another as a form of resistance. O'Leary emphasizes theater’s unique role in communal healing, where audiences co-create meaning through shared disorientation and emotional resonance. He also highlights the importance of live performance, noting that digital adaptations, while innovative, fail to capture the rhythm and intimacy of live theater. His work underscores the need for plays that don’t preach but instead allow audiences to confront uncomfortable truths about themselves and society. O'Leary recommends *Fairview* and *The Tomb of King Top* as essential reading, praising them for their unflinching realism and raw emotional power. He remains deeply committed to the collaborative, evolving nature of playwriting, believing that a play’s true form is revealed through performance, not just script. Currently, he is preparing new works including a musical, a ghost story, and a dinner-party play, all exploring themes of identity, memory, and societal conflict.

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Welcome back to the present process podcast where we talk about plays from playwrights that you may or may not have heard of, and illuminate the process of writing. I'm your host Daniel, and this week we're talking to Charlie O'Leary about his play Effective. As always, if you have a new play exchange profile, I highly recommend you go and give the play a read before listening. This episode may contain some strong language and other adult themes, and you can find an in-depth content warning in the description. Thanks for listening. All right, so I'm here with Charlie O'Leary, and we're here to talk about your play Effective today, and I'm super excited to do that. But first, I'm just sort of curious. I just want to talk about you for a second, figure out who you are, where you come from, what you do, and just how you would describe yourself. Yeah, I'll give you my 30-second life story as how I always start, which is not always the most interesting place to start, but we'll start there. So I grew up in Northwestern, Pennsylvania, in the middle of nowhere. I went to college in Northern Indiana, which is where I sort of learned about playwriting from my playwriting professor, Anne Garcia Romero. It's also where I met my partner who I'm still with today, so it gave me those two things, and we're going to just be grateful for that. And after that, I lived in New York for six years. I was mostly working in play publishing during the days, and then was writing plays and producing my own work in the evenings. In 2019, I decided to go to grad school. I moved to Iowa City to get my MFA at the Iowa playwright's workshop. I finished there in May, and my partner and I decided we liked Iowa City enough. We went to District around for another year or two, and I'm actually working in administration with the College of Education right now as my day job while I continue to write and send out my plays. And yeah, I guess who I am is a playwright, a sometimes lyricist. I came into playwriting through musical theater, and so I always have, I still love musical theater. I just wrote the book to a musical that had a small production in New York this past month, and I, yeah, I'm a playwright, lyricist, and just theater lover, maker, person who lives in Iowa City. I mean, I knew some people that came from Iowa and they say that the theater scene in Iowa is actually better than you would expect it to be. So it's really great for a city this size. It's actually, it's really fantastic. There's a great live performance scene in general. There's like a really thriving like stand-up comedy scene, surprisingly, just it's a, yeah, no, it has a surprisingly vibe, especially again, compared to like where I come from. I sort of am used to hearing small town and meaning a very particular kind of thing. And Iowa City is a nice little oasis in the midst of a lot of small towns that were more what I'm familiar with, which isn't no, anyway. Yeah. And I'm sort of curious. You talked about, you came from musicals, but I'm sort of curious right now like when you're working with plays, what types of plays do you typically work with? I mean, as a playwright, I feel like, especially when I'm writing non-musical plays, I think I used to say that I didn't write comedies. I sort of was surprised. We had a reading of my very first play ever and everyone was sort of laughing during it. And I was like, I thought I wrote a drama. And it just turns out it was sort of like humor is just embedded in how I write. So I now sort of lead with, I do write comedy. And I tend to write plays that are naturalistic seen by scene but that have pops of theatricality are really interesting to me. I like sort of, you know, really wild, structural twists or sort of, um, a peculiar, like formal conceit for a play. I really enjoy, um, I enjoy, you know, fast-paced dialogue and awkward humor. And I, uh, I enjoy putting bad behavior on stage because I think it, uh, it allows me to purge something for one. I think that just like, I can't have all these, like, thoughts running around my brain and just not, like, let them out somewhere. Um, but also I, uh, I think it allows me to, like, understand better. It's like a thought experiment where I get to see the life I didn't want to live. Um, sometimes is how I look at my plays. I also tend to be drawn to pretty dark work. Um, and, uh, my, my plays tend to be, um, are often gruesome sometimes. Uh, I had a moment recently where I was like, yeah, I think I like a lot of different stuff. And then someone was asking for play suggestions for production. And I kept sending them plays and I was like, oh, all these really dark. I think it's, uh, it's like moments like that where you learn interesting things about yourself. No, but I appreciate what you said about, uh, like people acting badly on stage. That sort of thing, um, cause I often feel like people go, we go to the theater not to see people act well, but to act in the ways that we wish we could sometimes. So it's like the things that we wish we could do that always aren't the right thing. Um, yeah. And like, and like you said, you're sort of exercising that from your body. And at the same time, we're all kind of collectively coming together to go, ah, here's a lesson in what not to do sometimes. Which is, I love that you're connecting it to wishing too, cause it is like, it is both wish fulfillment and then it, and then it is the realization that the fantasy of the fantasy were real would be a nightmare. Um, and uh, that is, yeah, I think just like really exciting to me, um, and I'm realizing now I'm like wishing is I, we just watched the end of the woods, like the Disney movie from 2014 last night, my partner and I, cause we had been listening to the soundtrack of the Broadway revival. Yeah, I mean, the movie is, it's not a good adaptation of the play, but I just, it definitely had me thinking again about like, oh, desire is, uh, desire in wishing and wish fulfillment is such an important part of like our, like lives as, as human beings, but also is such an important part of like what we're playing with a very dangerous element, potentially if theater and storytelling. Well, right, because like it's those moments when we let the wish and get on of hand on our side that make for the most conflict, and then that's right where we want the theater to be. Because if you just had a mundane, uh, people going around being reasonable on stage, it wouldn't be good. Right. I would not be compelling. I would not, I mean, I, yeah, I, my, um, playwriting professor in undergrad was, uh, really big into Marie Irene before Ness, it was all writing for the subconscious and, uh, you know, sort of writing before you understand what you're writing, which I still subscribed to today and that is sort of, uh, you know, uh, the way I like to approach writing, uh, but she would also just sometimes ask, like, what is the action of this scene? Like, what are we actually watching? And I, that's sometimes a useful question to ask because, um, you know, uh, we actually do want to watch something happen on stage, and usually that thing is conflict. Yeah. I mean, we'll get into that more as we get into talking about the play, but, um, yeah, I really feel that. And I think sometimes it can be, sometimes that's like what I'll send back to a playwright if I'm looking at a script for them is like, Oh, what like, what are they doing in the scene? Yeah. You have lots of interesting dialogue, but it's like what what's actually like happening right now, and then it's like, Oh, I need something like right, they need to be doing something at the very least. And then it can come from there talking about effective, um, which, uh, I love this play. It was, it was really, it was like on the short, short, short list when we were looking at production, um, and honestly, I'll probably keep it on my shelf for a while in case I ever want to do it because I really, I think it speaks to a lot of things that we're dealing with right now. I think it speaks to, uh, like, uh, I think in, uh, your pre-interview responses, you were talking about millennials, but even for, um, people younger than that, it really, it's just kind of like the work environment we're in right now. Um, but so you have this, uh, group of people who are working at a music publishing, uh, company who are making music for like high schools and stuff like that, and they're just budding up against the, the, the attitudes of the managerial forces in their life. Uh, and so what was sort of a personal or global event that might have inspired you to take on this topic? Yeah. I mean, I, uh, like, I, uh, I think I'm a person who, I don't think any of us are built to work office jobs from nine to five. Uh, certainly, I know, like speaking for myself, I'm, I, it is not something that I think that I, you know, uh, I'm naturally inclined towards and I had been working in offices at that point for five years, you know, uh, out of school, just having been in, you know, eight to five positions. And, um, there was, uh, something that had happened at like several companies in a row that I had been at, um, where sort of a new, a new management sort of a new person would come in and take over. And, um, and then there was this whole new slew of ideas that would sort of, uh, either be like out of line with the vision of the company or what the company actually does or actively work against what the company is, is trying to do and what the purported goals of even the new, you know, the new management or new leadership is. And, uh, I, I just felt like I witnessed over and over these like strange wars between people who had been in a place and were actively trying to keep the ship afloat and, um, people who were sort of swooping in attempting to make something like dazzling happen, uh, so that they could claim credit for it. And that these were like two really bizarre forces to witness as somebody who, like, frankly, was like, didn't really, I was just there to like collect a paycheck. I just like needed to like make a living and like was, uh, but you can't help but be caught in this like, in this battle. battle that is unfolding. And so I was, in 2018, very, very depressed. I was producing the biggest run of a show that I had ever done, which was at the People's Improv Theater. It was a very sort of whack-a-doodle satire that was very meta-theatrical and not-- it didn't feel like my serious writing. Although now I look back on it and realize it totally was. But I was just in the height of depression and the height of having been through several of these jobs where I had to jump ship, leave a company, because I felt like the environment was becoming so toxic and untenable. And it just sort of felt like that was going to be my life forever. It was like a spiral of jobs that were at places run by people I didn't respect or think were good at what they were doing. And oh, this is going to be public. You know what? It's OK. I haven't named any of this places. I'll make my LinkedIn private. It's fine. And it's also-- if you think I'm talking about you, it's not that company. It's the other companies I worked at. I think that I had just reached such a point of frustration into spare. We were also halfway through the Trump presidency. I feel like thinking about late-stage capitalism was starting to actually come into the popular lexicon and just with something that people were actively starting to discuss in conversation with their day-to-day lives. I'm realizing now I feel like the thing that most feels like it inspired the play, even though it clearly did not, was Elon Musk taking over Twitter, which is happening now. And feels like exactly what I witnessed, but in much smaller scale at so many corporate offices when I lived in New York. So the play really just came from a place of fury, I think, just a lot of anger. I think I was talking to another playwright and we were talking about how she writes when she's pissed off about something. And I feel like that is a great place to start. Because I think if you're upset about something, it gives you enough drive to keep writing those pages as you're going forward, whereas opposed to if you're really excited about spreading the word about something. It's maybe sometimes it can peter out. But who knows? I mean, maybe just because I'm more inclined to be upset about something myself. But I think I really resonate with that. So right, so you have this-- and I appreciate what you said, where it's like the-- it's sort of about-- it's inspired by Elon Musk taking over Twitter, where I think your play aged really well because, yeah, you wrote it in 2018, but then we got-- or it was starting in 2018. And then we got COVID, and we got people finally assessing like their work life balance. And they're going, is this really worth it to do this? And it's like this emotional damage on myself day to day. And I think that's kind of one of the core questions of the play is, is it worth it for these characters? And it's like sometimes, like you have characters who are saying, this is what I need. This is my next step. This is what I have, basically, or there are people who are trying to get a leg up, but then they can't. And it's difficult. So I think every character sort of hits a different facet of that reality in our current work experience. Yeah. Oh, and the question of, is it worth it? As you said, that just chilled me kind of, because I feel like the scary part of the play for me is that what is the alternative? The alternative is death. I think that we either live under capitalism or we die. And to live under it might mean hopefully to fight against it and to hope that there's a better version of it and a future where we can look back on it, look back on it fondly, as a part of our path that we moved through in order to get where we needed to be. But I also, yeah, it's like the COVID in particular in the way that we've all started assessing. Yeah, like is this worth it? And I think that so many of us are saying no, and then looking like trying to find the alternatives. And I guess maybe it feels actually, like there are more alternatives now than there felt to me as a 26-year-old writing this play in 2018. I feel like, yeah, there are maybe, is it worth it might have an optimistic answer potentially, I'm realizing, but yeah. - I actually have a question about that specifically. I was wondering if you would describe this play as sort of a cynical take on this perspective 'cause it doesn't necessarily end hopeful, like it ends sort of messily for the characters. And I think, I struggled with answering this question for myself, is it a, does it have a cynical outlook on this? Like is this actually a good way for these characters to go forward? Or is it, and that's kind of the absurdity of it, is they have to accidentally kill their manager to move forward? - Yeah, I think, I mean, obviously, like these characters are in like, have really put themselves in a pickle at the end of the play. And then like, the final monologue of the player, the final movement of the play is not like, you know, it's not like uproarious or joyful by any stretch. And I think the play in general, I would say is very cynical about the systems of the world we live in. I don't think it's like particularly hopeful with regards to like, these like businesses or systems or structures. I think it is hopeful for the people within them in that like, at least, there's like, for me, there's a little, there is a little bit of that like guillotine fighting back moment at the end of the play of like, we may be monsters. That is what the system has made of us. And we as monsters can now like, bite back or claw back. And that feels very scary to me. But also there is perhaps something hopeful in that. Alongside I guess just, I think the larger, maybe sort of the other way of putting it that might be less violent or less rooted in violence. For me is just thinking about the final lines of the play, which are, you know, what's your greatest weakness and the other character responds, I care too much. And I think like, that hopefully is a punchline earlier in the play that like comes back in this slightly different context here. But I do think that the idea that we care too much is both a thing that like makes us victims of like late stage capitalism in these kind of environments and can also give us the power to maybe change those systems. So I think that the fact that we care is the only reason that there, we would have any like ability to hope that there is an alternative that like that, you know, when we look to leave these kind of like horrible dead end jobs like that there might be an alternative world out there waiting for us or like for us to create. Right, and I think that's even reflected in the lily monologue right at the end of the play where it's like I'm excited like where lily says I'm excited for this to be over. Yeah, I'm excited for this, yeah. And we can all sort of feel that and it's not, I don't think the play ever says, oh, this is changing, right? This is, it just says, this is sort of the human spirit, right? It is, it's a triumph of the human spirit where it says we're gonna move forward in a way and hopefully find a way out of it. But then at the same time you have that sort of absurdist twist at the end where it's like, oh, well, this is kind of reflective of the beginning. Are we have we really moved on? And so in that way, I think it, I talked about this with another play where I'm like, I don't really know if I like plays that are super cynical. Like I like where it's just like at the end, you're like, oh, everything is sort of over. But I think, I think you're sort of gets around that where at the same time it, it identifies and it respects the fact that we still live in this world. But also, there's still us, right? Like people and our ability to move forward. And I really appreciate it that you did both. - Thank you. That means a lot to me. And it's interesting that you say that, or that that was even a question that came up was because I had a play that I worked on for, I rewrote more than I've rewritten any other play. I rewrote like 60 drafts of this play. And like the thing that I finally shipped away at that like the reason the play wasn't working was that like the first drafts were too cynical. They were like deeply cynical towards the characters. I didn't love my characters. I didn't understand them. I didn't care to understand them. And that's a really, it turns out that just doesn't, at least for me, I was not able to do a good play. I was not able to turn that into something interesting or compelling to watch. And it was only as soon as I cared about the people and like felt stakes in their lives. Even as they like did atrocious things and engaged in an atrocious world, like that they're needed to be something optimistic or hopeful in, again, not necessarily in the grand scheme of the play, but at least in those characters that we care about that we identify with. Yeah, that feels really fundamental to me. And I don't know if I would have said that five years ago. So that's maybe that's gross too. Well, I feel like for me, it's like right, the basis of theater as an art form is about social betterment, right? Like people would gather together. They're like, okay, we got a Greek theater. We got all of our political problems to figure it out. And I think that it hasn't changed much. And I still think that's sort of the mechanics of theater in a way, that's the way it's different than film. As I think it does turn the mirror back on us where film is like, oh, we can just look at someone's life for a while. And so I think it's important that it's just not like a play is never completely cynical. Because otherwise people just leave in their life. like well, I guess, I guess there's nothing we could do like to solve our problems. - Yeah, I like, no problem has ever gotten solved that way. I've been talking to friends recently who are like going into like aerospace engineering to see if we can like, you know, create like, is there any way to basically take the air in the air travel industry and make it like sustainable? And if not, like what do we do to just shut it down? Is sort of like their approach and I was like great. I'm glad someone is doing that and has hope that like, that is possible because I mean, the alternative is just to like give up and party for 30 years and accept that the world is over which feels really bleak I mean, because it is. - When you were looking at your play and you were like, you were fine tuning it, you were fixing the problems that you might have had with it, was there ever anything in there that you ended up cutting that you really really liked? - You know, yes. So there's a moment in the final monologue and this was, this is a cut that needed to be made as you're asking about like how's that need to be made? Kill your darlings is like about no one like enjoys it but it's necessary. So I originally wrote this play for a project called the Brooklyn Generator where you gather a director and a group of actors and you have 30 days to write a play for that specific group of people and you do a reading of it at the end of the month. And so you have four hours of rehearsal with this like brand new play that goes up in front of an audience and all your theater friends come and your play running friends come in and you just hear this like weird thing happen on a Sunday afternoon. And it's a very special process to me and I've done it twice now and I've been to dozens of those readings over the years and I just think it's an incredible process. And one thing about knowing exactly when and where and how a piece is going to be performed is that like even in a reading setting I can then do things that are like that remind us that we're in a live moment that is going to disappear and one of the ways that I did that was in the final monologue of the play which referenced the day that it was written which was just a few days before the reading at the time. It also dropped my name like it allowed the audience to realize that the character of Lily or the actor playing the character of Lily was now speaking sort of as not just like as the voice of the playwright but literally as me Charlie O'Leary like a character who the playwright and also like a person who has now entered this play. And there was like a weird laugh and like an uncomfortable shift as soon as that happened because it happened right before the monologue sort of delved into some really much darker material and it came off the tail of like a story that I knew some people in the audience knew about like my partner and I who met it in college and the thing that I am sad that I had to lose was just the like moment of actually like your suspicions are confirmed. The audience like this you're hearing a diary entry now this thing that you thought was a play is all of a sudden become something different in your eavesdropping and that was, I mean that was the thing that only works if you like came to the play knowing who I am and that I wrote it which you would only do if you were like a friend of mine. Like thewrights aren't like unless you're any baker no one goes to your play sort of knowing who you are or caring frankly and nor should they. But I realized that I had to communicate in other ways that that character was not Lily but rather the voice of the writer or the voice of someone else and I found other ways to do that but none felt as like elegant or as shocking as just like saying my name out loud. And I also like I'm sad that like the play doesn't just exist on that one day that it was sort of originally meant to be read. It's sort of weird that it exists in a form like that other actors have played those roles. And again, it's good weird and it's like the play has evolved since then but yeah I'm like, oh wow, I guess I'm like the thing I was sad to cut is like my experience of the past of the Affemarality of Theater. I was really sad to cut the Affemarality of Theater. - Yeah, but that's it. Yeah, that's the sad part but it's also like the necessary one. I think like right, if you have that in there. I think if you left it in there for anybody else reading it who didn't know you, it's a little bit-- - If you have noxious, it was obnoxious. Like it was obnoxious even in for what it was but hopefully it's slightly less obnoxious. - What you run the risk of when you do that now is sort of it's a little bit alienating. Right, like if you left that in. So I think now that I think that cut gives your play legs which I think is important. Like if you wanted to have like some people just write things for that moment's like that, right? And that's the kind of theater they do but-- - No, but of course, like obviously beyond that, I want the play to like have a life and like I want the play to be seen. And I like, you know, I think that every writer has to believe that like their writing is worth being heard by at least. Like a couple of dozen other people and like you're like just searching for them and just trying to throw it out into the world at them. - Right, and even like you're just waiting for someone to connect with your work the way that you connected with some other play that you read, right? And it's just a-- - The way that like, I don't know what the constitution means to me made me feel like so deeply seen and like also like like I had grown as a person every time I saw it. Like I was like, oh, I don't think that I can do that for as many people as Heidi Shrek did but like maybe I can do that for like five like random Kingsters in the queer community and like a weird teenager in Minnesota. Yeah, no, I think that like wanting to see and be seen is like the reason we all are writing and also consuming stories and all of it. - Yeah, and then it's through that. It's not that we're solving the problems on stage. It's that by expressing those problems and then connecting with people about them, it brings them into the dialogue again and then we can go, okay, now that we're thinking about this again, let's talk about it, right? - Yeah. - And then you process it that way. So it's like whenever you have a problem play or like an activist sort of thing, it's like write it, it's cool for the people that agree with it in the audience but I don't think it really changes that much. If you have a deep heartfelt play that connects to that problem and then people can talk about it, I find that that inspires at least me to do something more than some a play that tells me to do something. - 100%. When I think that, I mean, this is a shitty example but like as a gay man or as a person who has thought a lot about like gay theater the last like 40 years in and around HIV and AIDS, like the normal heart is like an important play and I saw the revival on Broadway in like 2011 and I wept. But like it is not like angels in America, I think like helps me understand the world and also like potentially even the crisis of HIV better than the normal heart because it is like due a like because it is fundamentally about like examining a human truth and not about like conveying a really particular political message for activists ends which again is like really important and should be done and I think the normal heart is like I'm glad that that kind of work exists but it does feel like it is a form of activism more than a form of theater and again, like I think that I am very suspicious of that phrase like art is activism I'm like well no, activism is activism like go like do something and write an angry letter and call some people is like probably more productive than like pouring it out into a play and yet I think and yet it's the Greek model that you're talking about like that by sort of providing folks a framework to think about these issues in a human way like we can actually maybe begin to understand them and that allows us to like take more thoughtful actions I don't know maybe the maybe this is like called normal heart angels of America thing is really stupid and can just be cut but I think that like yeah, when I think about like what was more important and more needed I guess at the time it was the normal heart and when I think about like the reason that angels of America is the longstanding play that like we hold with us and that will document that moment in history you did originally you did the generator and that's where the place started and then if I'm understanding correctly you did another reading that was a digital one and Sarah was like you know basically we both agreed that like in fall of 2020 we were looking at the COVID numbers the production was supposed to go up in October we were like we can't do there's no way we can do a live production there's this is like before vaccines like it just like the theaters faces weren't ventilated in such a way that like there was literally no way to do this safely how do all our actors quarantine for several weeks and then film them and then broadcast a film of it but if we're going to film it anyway like we might as well just keep people safe and stay you know keep them in their homes is what we did and so we with designers and you know a stage management team ended up basically creating a film of the play but like one that was that used zoom boxes but was designed in such a way and staged in such a way to like sort of constantly be presenting the illusion that we were sharing a space or that the characters were sharing space so they would like pass papers back and forth between each other and there were like moments of like intimacy that were like choreographed by an intimacy director that like one I thought that was such a brilliant solution one actor had like a tie just off screen that he would grab as the other actor sort of used his like off screen hand to grab his own tie and pull it forward So these ties were getting pulled from both frames at the same time. and they pulled each other off screen and had a moment of intimacy that we didn't see, but that was implied. Anyway, all of this just to say, I learned from this production a lot about how to make a zoom play, which is a kind of play I hope we never have to make again. Sarah and our designers and our actors were so brilliant. It was such an incredible, incredible team. And I'm like, I could not be more grateful. And I did learn so much about, but I also learned that the rhythm of this play and of this dialogue is really meant to be experienced live in a room and that it's really hard to replicate that on zoom. As a result, I learned less about the moment to moment beats of the play and more about sort of like what I was exploring thematically. I don't think I could talk about the play the way that I have been, which is not even like particularly eloquent, but like I am usually if you ask me about my own plays, I am just I turn into like a babbling child. I just it nothing comes out at all. And I have at least formed two to three sentences with periods in this time so far. So I think that's and I think that's really a credit to that workshop production. It I think if I were ever to do something like that again, I would write something specifically for that form that wasn't trying to like emulate theater in the only way we could, but was that, you know, but that was like being its own weird zoom thing. I think of like Eliza Bent had an amazing play called Karen. I said that she performed over zoom that was like so beautifully for that that form hot. And I I think that like those works are like what I'm going to remember about the zoom era, which I mean we're on zoom right now. We're still we're not out of the zoom era. COVID in fact, the pandemic rages on. However, we can sometimes gather and and you know, where I'm asked in theaters and see a live play once in a while. So I both learned a lot about the play and then I also feel like in some ways, I, you know, I'm still waiting to like be back in the room with this play. Yeah, I wonder. I feel I get the impression sometimes with. I think there are different kinds of playwrights. There's some playwrights who just kind of like write their play and then they send it out and they just like don't touch anymore. And I think there are other people that would love to just like are always invested in it because they're always curious to see where it goes, right? Like they're always want to see, well, who's who's interpreting it now and how is it going to change? And so like, what can I learn from that because I always learn like any time in a new actor takes on a character of mine, I learn something new about the character and sometimes not in like depending on where the play is at and it's, you know, in its development cycle, which this play is both old and and in some ways like, you know, early in development, you know, I feel like I could learn so much from watching actors and have at these roles that might impact the writing in ways that might, you know, deepen their journeys or like even just deepen the comedy, I think like being in the room to rewrite a comedy is really essential. I was not able to be in New York for the rehearsals of this like musical comedy and I regret that because as soon as I heard some jokes and like with an audience with like live actors, I was like, oh, I know exactly how that needs to be rephrased to work. And I won't get to until the next production, right? Just to go through that process of working in like a rehearsal room, it's just, that's like that's such a, like a, it's a privilege, almost like. Yeah, especially because it's kind of like the beautiful part about theater is where you have all these people getting together who are like agreeing that, okay, we're going to focus on this idea for a hot second, right? Which I think is so, like I'm always grateful when people let me do that, like let me, like they don't have to do that. No, I mean, when I think about just as like the thousands of collective hours that people that actors and directors and designers and dramaturgs and stage managers and all sorts of folks have put into my work, it is mind boggling. It is such an incredible gift like and it is, this is one of the most like time intensive forms of, or like as a form of writing, playwriting is one of the ones that requires the most other people, the most amount of time and energy and effort to make it happen. And to make it the thing that it's supposed to be, and yeah, no, it's, that's an incredible gift. And I always like, I can't imagine not wanting to be there for almost every part of that process. Sometimes you get like three weeks into staging and like, you know, they're just. So when you're actually going about writing, what sort of like process do you have? If you have any, because there's plenty of writers who I've talked to that are like, yeah, I don't really have like a process at all. So I, my terrible joke and you can take this out if this is inappropriate, but my latest joke about writing has been that writing is like doing Molly, I absolutely love it, but I can only do it four times a year. So and I feel like lately I've just been writing in sprens, I just like, I will, you know, write for four days straight in just sort of like a manic episode and like write an entire play in that period or, you know, almost an entire play in that period. I also sometimes will write, you know, 30 pages and rewrite them and rewrite them and rewrite them over the course of six months. In general, I would say though, my process is to like think about an idea and think about characters and do research into a world for six to 12 months and just like let an idea just date. And then try to write the first draft of it really quickly as soon as the play shape comes into mind. And I think I usually tend to know the shape before I write the play and again, once that shape is there, I like want to fill out a skeleton and, you know, make sure that I have something that is a first draft that happens really quickly. And then I think where that tends to happen really quickly and then and then it's just like a matter of like rewriting over a period of weeks and months, which usually involves hearing the play allowed with actors usually involves sitting on it for a month or two, putting it back in a drawer, pulling it back out and rebreeding it and being like, wait, I wrote that, I don't remember that part. Like, what's what's going on there? And like, oh, like you were really obsessed with like grapefruit at this period of your life, Charlie, whatever it is. And I think the rewriting process is the part that always is like the hardest and longest and scariest and also like weirdly has the least is the one that I know the least about. Like it feels like generative writing should be the one that is the most mysterious and it is in so many ways more mysterious. But I sort of know that I just need to like chew on something for a real long time and then like write it before I think about it too much. I at least know that much. It's the plays that I haven't finished are the ones that I just like really took my time on and never set a deadline where I was like or they became other plays effective actually there were 20 or 30 pages of another very similar like angry office capitalism play called idiot boat. I looked back at it was it was interested in totally different things stylistically, but like in it became effective, but like the reason I didn't write it was just like I took too long to write it like it's just by the time I like figured out what it was I wasn't interested in anymore. I mean, I think you touched on right like this fact that you need to sort of like let it sit, which I think is it pretty common. Trade among playwrights is this idea that you sit with an idea it's not saying that you're not doing writing like some people will do a little bit of writing here and there for an idea some people don't do any and then they do it all in one go like you were talking about. But it's a sort of idea that you just need to be like have this idea be present and it will be because it'll bother you right because you'll be thinking about it. Yep, and then you develop that over time and then you go, okay, I think I'm finally ready to put some words down that are like a script and so I don't I don't think that's that uncommon. I like from what I from talking to people or the playwrights that I talked to are writing plays that I like the plays that I like are written in that way. So there might be right I'm sure there are like right every day playwrights who are like turning out really interesting and exciting work. I just I am not I don't subscribe to the right every day here. Well, I also one of my professors and this is I think just like a summation of all of what we were just saying both of us is typing is the last part of writing. I she said that to me once I think about it all the time and it is it has been very useful to me when I like am inclined to beat myself up for not you know for not being a right every day kind of writer. And it's because of course like yeah, my pleasure present with me every day the ones that I think about every day I think about every day like while they're while they're in my brain until like they passed a few years later. Well, it's weird to think about the right every day mentality talking about your play and sort of like the the work style and work like life balance like once you once you start teaching or once you start turning your art form into a job. Like yes, that works for some people, but also sometimes it can make you sort of load having to do it and I don't think when you're when you're loathing the process that it produces any sort of good work and so if you're frustrated with what you're doing. Sometimes you just need to be like I'm done like I'll take a. Yeah, I'm realizing as you said that I was like oh effective was it's a play that is very much about I feel like one of the emotional course that it came from that I wouldn't have been able to recognize at the time. But like that I'm now seeing years later is like I was very I had turned a playwriting into a it's own rat race I was like oh I have to write two plays a year and I have to submit to these things and I have to make sure that I'm getting a reading of this every like six months or what. It is I think useful to have like things that are like setting deadlines keeping you moving forward just keeping you invested in your art making. What it was was that I started to care about playwriting as a career more than playwriting as an art form and that leads to despair I think and also bad art. But for me mostly despair is where where it led me with this play I'm realizing that's yeah and probably not surprising just given the general tone of the play but well I think that and then I think that feeds into when you have the final like this. the monologue at the end where it's from the perspective of a writer and then you can sort of, it's not like, it's not overtly connected. Well, especially because you have characters that talk about how they genuinely enjoy the field that they're in, like the work that they're doing, but like the work, like the job that they have makes them sort of hate it at the same time. And so I think we do that to ourselves sometimes. Absolutely. It's, um, astonishing our ability to kill our own dreams is a crazy sentence that just came out of my mouth. And, and what a shame. Um, and I, I guess, but there's always the ability to recapture that. Um, I think like that, that love of the thing, I, I think once I accepted that like, I may never have a play at playwright's horizons, but like, I can always get my work out to people who will invest in it in some way. And like, that is a huge gift in and of itself. And the fact that I have that is like something to be grateful for, like sort of making that paradigm shift is like, uh, very freeing. It's deeply freeing, I think. And I, it's, it's like, I have a, like my own, my only like personal superstition is that I only get things I want when I stop wanting them. Yeah. We're experienced that where it's like, yes, when you're trying really hard to do something, uh, and then the moment you go, okay, well, I guess I'm still gonna go for it, but I'm sort of resigned to the fact that it's not gonna happen. That's, that's what it starts to turn around. And I think it's, I think it's because once you're in that moment, you're sort of free to, you're not inhibiting yourself anymore, because you're not trying so hard. Yeah. Exactly. Right. And, and, and I think in, because you're being driven by like, this is a little like cognitive behavioral nonsense, but like, I mean, not nonsense. I'm very much, I end of it. Um, but like, I think that's being driven by values rather than by like goals or like looking for like the, the, you know, uh, prize at the end of the tunnel or like the, the, um, treasure chest at the end of the, uh, rainbow. I'm Irish. I'm allowed to use that terrible image. Reaching for that in that one specific thing always means that as soon as you get that thing, then like, then what do you, what do you have? Like, what are you going for? What's driving you? Whereas like, if you were driven by the things that matter to you and by your values that are sort of like that are not, uh, going to, that have no end. There is no end point in the same way that I think there is no end point to like, you know, trying to like make a better world. There's just like, we're never going to achieve the perfect like utopia. And um, that doesn't mean not to strive for it. Um, wow, I really, that's so wild to think about it four years ago, if you would ask me like, what I really wanted as a playwright, I would have said like, yeah, like, a production at Soho Rap or whatever it was. And like, I truly like, I mean, I don't, I don't want to say that that wouldn't matter to me now or that I don't like still want that in some way, but like, wow, that's like truly not driving me anymore. And it is, that's why this play feels so distant from me, I think I feel very like removed from this play in some ways. It feels like a little bit like meeting them play from another lifetime, um, revisiting this play. Uh, even as it, yeah, again, like feels like it's about Elon Musk. Um, I, I think that's the, it's like, that's what, I, well, I think art in general does that a lot where like, you're capturing a specific moment in your life, right? And even though you're developing over, over a long period of time, it's still a very like isolated, like, this is your personality at this moment, whereas like, my person, like, your personality changes from year to year, like, you're never the same person. And so I think that's, I, I would say that feels like it's pretty common too. But then I guess, I bet there's plenty of playwrights that just like, are, have been super consistent, right? And that this is just, they like, they're very familiar with their work. But I mean, I, I, I'm, I'm, like, I'm generally a young artist. I even look back and things I wrote two years ago, and I go, what was I doing here? Like, what is this? When you can sometimes like, understand, I understand like, what was troubling me at points in my life by reading my plays years later. I was like, oh, that's when I finally dealt with like, that religious crisis. And that's sort of when I was really dealing with like, I mean, suicidal ideation comes up in this play, but like, I wrote a play that was like very much about that. And it was like, oh, I didn't realize the way that that was under the surface of everything at that period of my life. We're like, yeah, I, and it, it always makes me excited to look back on the things that I'm like, I've right now that I'm like, I don't understand what's going on here. And, and then actually figure it out years later. I've been writing a lot of like, you know, relationship anxiety, like, growing into, you know, the middle of a relationship plays recently. So I don't know what that's about. You know, who's the side? Yeah. I don't, it's such a, and I think it's because it's a, it is a collaborative thing. So you never really know what something is until you get it in front of someone else. Like, I don't know, I don't really know what it's like for writing literature or like writing like a film script or something like that. But I, I just always keep the feeling with theater. I never know what a work is until actually people are together and processing it in a communal way. And so I don't think it really reveals itself until it's right there. And maybe that's, that's getting a little too mystical about it. But not at all. I do feel like that's the case. If you would ask me at the beginning of the process, what I thought I was writing about it, I would be like, oh, like age gap relationships and like Gen Z tender queer, you know, internet politics. And then I sort of did not realize until I was watching it. As you said, with an audience having this communal experience that I was like, this is a play about my deep seated fear that I am evil. And like, that I am capable of great evil. And like, it is about like being scared of that. And like, it is really, it was that simple. And it was a much simpler play, I guess, in any ways than I thought it was. But I had to have the community. So I think, I thank the community for coming together to give me the therapy. I so desperately needed. But also, but also, no, I mean, it's to understand, I think that like that kind of understanding is a thing that we do do together. And like, I love theater as a space for that. I think it's a really important space for that. It's one of the only like collective fantasy spaces we really have in our culture right now. It's one of the only spaces where we go together and sort of collectively imagine. Especially because you're in a space with people and the audience is always kind of, it's like what sort of separates it from film like right film. You get to go into a dark room. Everybody's everybody's in the dark. You're all watching the same thing. So it's collective still, but it's still not quite the same because in theater, you're always aware that there are other people watching with you. And you're always sort of taking that into account. And I think, I don't, I mean, especially at this point, I don't think we can ever escape. I don't think I think the fourth wall is gone. Like we can't, we can't ever build it. I can't because now people are constantly aware of it. And you know, for the better, because like it was never really, you know, like we've always, the point has always been that we like are sharing energy with the actors, like whether or not, I mean, like, we're talking about like sharing air or sharing breath, which now gives me like COVID anxiety. But like, we sharing energy is that's the, that's been that for me also speaks to the different teaching film that we're talking about, which is like, the actors aren't going to nothing about the film will change. Even if the audience has a big reaction to it, the play changes when an audience reacts to it. The text, I mean, again, the text is not literally changed, but like the, the text in a sort of like grand, you know, whatever interpretive sense, like does does change. I think that like what we are literally seeing changes as a result of like who is in the room and of people experiencing it together. Anyway, I'm always there to get mystical about theater. This is my bread and butter. So I B2, I totally agree. That's anytime you can wax eloquent about your art form and whatever it is, I think is always a good time because it makes you feel like what you're doing is, is as some significance. Yes. When you work in the American theater, it's very easy to, you know, sort of not feel that significance. And, you know, who's to say why? Alright, so sort of winding this down. That's closing things out. I'm just sort of curious. I know you gave me a long list and I really appreciate that because I'm always looking for a new place to read. If there's specifically like a work that you want to recommend to people that really inspired you or you think that's like a really, really just great play that people should read. Yeah. I mean, the play that I've been telling people they like need to read from, you know, every day for the last like four or five years since I saw it was Jackie Sible's Jury's play Fairview. I think is so stunning. It is such an incredible theatrical like trap. It just like operates. The mechanics of it are so perfect and so brilliant. The writing is like so sharp and like so just effective. And the turns it takes are like so thrilling and such a gut punch. Yeah, I think that that play is like the essential reading play of the last five years. And then, yeah, again, like I think of lots of plays that are important to me. But the Tomb of King Top by Olivia Dufo, I always have to throw out. When I teach my students, I always love that play. And I cannot stop thinking about the play. I thought I would die, but I didn't buy almost blanked in your name, Bailey. I'm so sorry. By Bailey Williams, who just had to play events go up in New York that I'm so jealous I couldn't see, but that play just has haunted me. If there's any way that you can get your hands on a copy of the script, I think it might be a new play exchange, but just hunt it down. It is. I like plays that punch you in the gut. I think is what I'm saying. Well, that when I saw a red fair view, I didn't know anything about the script. I never I haven't gotten to see it, but I was like, okay, this first act is pretty standard. Like it's a fine play. It's good. And then I got to act two and I was like, what are we doing? And so I highly suggest if anyone wants to go read Fairview, just read it. It's great. Like you have to just like, let it happen because that reveal for me was really intense and I was just reading it. I was like, really we're going to do okay. All right, we're doing this. Yeah. And it was singing the theater. I just like, yeah, I was like, I mean, it's just sort of like everyone. Like, what is, I mean, yeah, which I love. I love disorientation in the theater. I love let it's like a safe space where I get to be disoriented. Fairview is also like is what I found for recent trend where like playwrights of color not giving a shit anymore. And so they're like, no, this is the reality. Like they're like, this is what we deal with and you have to deal with it too. And it's no longer like, oh, but we're going to have a good character who's like a red like a redeptive white character. It's like, no, there are no more of those characters left. We tried that and it didn't work. So that's also a lot of those lines too. And it's so good. Just real quick, finishing up with you, where can people find your work if they're looking for it? Yeah. A lot of my plays are up on new play exchange, Charlie O'Leary. I have a website, which is the most embarrassing sentence any one person can utter, but I have a website. It's www.CharlieHoleary.com with no apostrophe. The apostrophe is sort of the ban of my existence. My partner has an accent in his last name and so I was like, if we ever like have kids and have to like have a hyphen, they're going to like have a hyphenated apostrophe accent at last name. It's going to be really fun for them to fill up forms and and make websites. CharlieHoleary.com and new play exchange are the best places to find me. I'm also, I am on Twitter at the moment and we'll see if that lasts for more than five seconds longer, you know, but I'm on Twitter is the bath years and Instagram as well. And also TikTok, because I'm Gen Z at Hard. Well, perfect. And are you working on any projects right now that people might want to expect or anything that you can share? That is. Yeah. So I'll have a production of an AXMIS story, which is the musical that just went up this past month in New York. It's having another production at CAP21 in New York, the musical theater conservatory. And that'll go up the first week in the March. I have a reading of a play called Ridgeway, which is sort of a ghost story about the question of whether or not my hometown was a was a sundown town. And a that play is having a reading at Alliance Theater as part of the, it was a condate a competition finalist this year. So it'll have that reading also at the beginning of March, I believe that's the second week of March. And then I'll have a reading of my new play, The Doctors with the Road, The Getter Company in Los Angeles, and that's a play about pain and nostalgia and the way that we remember things really differently. It's also just, I wanted to try writing a dinner party play. I wanted to write like a play where four characters sit in a room and like, have arguments to see if maybe that would be producible. So it's sort of that and then, and then weird stuff starts happening and you know, like the furniture doesn't work right and then it does my usual nonsense. So yeah, I'm really excited about all those plays and I'm also I have in the hopper a play about Super Smash Brothers in 4chan that's like a play about the rise of the alt right. That's amazing. Well, Charlie, this has been fantastic. This has been a great conversation. Thank you so much. I really hope people check out your work because I think it deserves more eyes. So thank you so much and thank you for having me. This was such a fun conversation. I really appreciate it. Thank you so much for listening. All our music was written, performed and recorded by Devon Wessels. Our graphic design is done by Lucas Minarchic and next time we're going to be talking with April and Mara about her play, title, pending and be sure to support your local theater. They're doing great work. See you next time.

Podcast Summary

Key Points:

  1. Charlie O'Leary's play *Effective* draws from his personal experiences with toxic workplace environments and the rise of authoritarian management, particularly inspired by Elon Musk’s takeover of Twitter.
  2. The play is dark, naturalistic, and structurally inventive, blending humor, awkwardness, and theatrical absurdity to explore the emotional toll of modern work culture.
  3. O'Leary initially wrote the play in a deeply cynical tone but reworked it to center empathy and human connection, believing that characters must be relatable to make the play compelling.
  4. The play ends messily, with a violent turn—characters kill their manager—to reflect the desperation of systemic oppression, yet ends with a subtle hope rooted in the human capacity to resist and care too much.
  5. O'Leary emphasizes that theater’s power lies in communal experience and shared disorientation, where audiences process pain and truth together, not through didactic messaging.
  6. The play’s themes of work-life imbalance and choice resonate strongly with current cultural concerns, especially post-pandemic reflections on productivity and mental health.
  7. O'Leary values the collaborative process of rehearsal and performance, noting that live theater transforms a script into something dynamic and deeply human through audience interaction.
  8. He recommends *Fairview* by Jackie Sible and *The Tomb of King Top* by Olivia Dufo as essential plays that challenge traditional narratives and offer raw, powerful storytelling.

Summary:

Charlie O'Leary’s play *Effective* is a dark, satirical exploration of toxic workplace culture, inspired by his own experiences working in corporate environments and witnessing the rise of authoritarian leadership—particularly Elon Musk’s takeover of Twitter. The play blends naturalistic dialogue with abrupt theatricality and absurd moments to depict the emotional and psychological toll of a system that values performance over well-being. Initially written from a cynical perspective, O'Leary reworked the play to prioritize character empathy, showing that even in its most violent ending—where characters kill their manager—the human desire to resist and survive remains central.

The play reflects on whether modern work is worth the cost, questioning whether capitalism is a necessary path or a form of emotional and physical destruction. While it ends in chaos and ambiguity, there's a quiet hope in the final lines, where the characters acknowledge their deep care for one another as a form of resistance. O'Leary emphasizes theater’s unique role in communal healing, where audiences co-create meaning through shared disorientation and emotional resonance.

He also highlights the importance of live performance, noting that digital adaptations, while innovative, fail to capture the rhythm and intimacy of live theater. His work underscores the need for plays that don’t preach but instead allow audiences to confront uncomfortable truths about themselves and society. O'Leary recommends *Fairview* and *The Tomb of King Top* as essential reading, praising them for their unflinching realism and raw emotional power.

He remains deeply committed to the collaborative, evolving nature of playwriting, believing that a play’s true form is revealed through performance, not just script. Currently, he is preparing new works including a musical, a ghost story, and a dinner-party play, all exploring themes of identity, memory, and societal conflict.

FAQs

Charlie was inspired by his experiences working in toxic office environments, particularly during a period of job instability and burnout. He also draws from the real-world example of Elon Musk taking over Twitter, which mirrored the chaotic and disruptive leadership changes he witnessed in corporate offices.

The play is largely cynical about corporate systems but offers a fragile hope through its characters' deep emotional connections. The ending is messy and dark, but includes a moment of resilience where characters recognize their own capacity to resist and challenge the systems that have oppressed them.

He often lets ideas develop over months, thinking deeply about characters and themes before writing. He writes in bursts—sometimes completing a full play in four days—then spends months rewriting, revising, and refining the work through cycles of reflection and feedback.

He values the live performance setting because it creates a shared, real-time energy between audience and actors. The presence of others in the room alters the experience, making theater a communal, dynamic space unlike film or pre-recorded content.

He originally included a moment where he personally speaks as a character, referencing the play’s creation date and his identity. After realizing it would alienate audiences, he cut it, but kept the emotional core of the moment—showing how personal experience shapes the play's meaning.

His plays are available on New Play Exchange, and he has a website at www.CharlieHoleary.com. He is also active on social media platforms like Twitter, Instagram, and TikTok.

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