On the importance of getting out into the world

You write plays and books, and you write for TV, and you write your own newsletter. Why do you write in all these different formats instead of sticking to just one or two?

I can answer that in two ways. One is from a craft standpoint, I do find that every form feeds into the others. A really good example was that I think the column I wrote for Elle was successful mostly because I had a background in playwriting, so I was able to create a character that was a version of myself. The column was written as myself, but it was a bigger version of myself. Every column, I kind of approached like a frantic monologue. That’s a skill I wouldn’t have had if I wasn’t a playwright. And similarly, the newsletter helped bring me out of the elevated voice and feed into the memoir writing. They all make me better.

The other side of the answer is that I get very nervous that people are going to get sick of me, or that I’m going to get sick of myself, so I like to have a lot of irons in the fire. It’s really exciting to me, but it also is fueled by panic, like everything I do.

I’m surprised you’re nervous about people getting tired of you. Can you talk more about that?

One of the strange things about creating in our time is that any creation has now become creating content. I don’t think of myself as a content creator, but that’s sort of the paradigm in which I’m working. Because I write books that I would like people to buy, because I can see the open rate on my newsletter, and because I write plays and can count how many people are in an audience, I’m always aware that I’m not just creating for the sake of creation. I’m also creating for consumption.

And the positive way that I understand it, and I really do believe this, is that creating is sort of community-making. And I want to keep making community, and I want to respond to the feedback I get from the community that I’m trying to make work for.

It can be a little bit nerve-wracking to think that the people who I’m writing for, even though I may not know who they are, won’t always be interested. You never know when your time is up. There are plenty of artists that I used to go hard for, and now I’m like, “I don’t think so. I don’t really care.” That’s fine, but I don’t know what else to do in my life. And I’ve done a lot of things.

I’m not nervous about figuring out what to do, but I’m nervous about losing the community. I don’t want people to get sick of me, because I’m also writing humor, and humor has an interesting shelf life, but it also has a serious core. I want to make sure I’m still in tune with what the community wants and the conversation we’re having.

We’re talking about a sense of community, but from what I understand, most of your writing is pretty solitary. How do you make sure to get other people involved?

It’s become so prominent a need for me to be in conversation with other people. I got [The Ever Present] commissioned about a month before COVID. And the play was originally supposed to be about climate change because I didn’t know there were other disasters to be sorted out. It was a miserable writing experience because I was so separated from my process. It didn’t turn a corner until I was able to sort of re-engineer the community around me.

Over Zoom workshops and casual conversations, I seek out a lot of feedback. I’m very fortunate to be in the position to not just ask people to read things that I’m working on or talk to me about ideas, but to say, “Hey, can I pay you for your time?” Which is very important to me, but not something I was always able to do. I have a lot of brilliant friends to whom I say, “Hey, can I get two hours of your time on Zoom?” And we talk through the issues I’m having.

It’s also so crucial to me to just be out in life. I’m working on a pilot for a sitcom with a studio. It’s been sort of herky-jerky, slow-going. I haven’t been able to crack the series. And then, I was finally able to go back to Tavern on Camac in Philadelphia, which is my favorite bar. I hadn’t been there in two years. And then I went to a small wedding in Brooklyn and met some weird characters there. Soaking in socialization, in casual conversation and hearing people walking down the street, talking about stuff and having that ignite things in me, that changed everything for me. I rewrote the outline of the pilot, and one of the execs was like, “What happened? This is so much better than what you’ve been bringing us.” And I was like, “Oh, I got to leave my house.”

I didn’t realize until the past couple of years that as much as I’m doing solitary work, everything I do is built with the fingerprints of other people, strangers, baristas, friends, and editors. I have to become much more intentional about pulling those people in early and maintaining those connections.

It sounds like one of the main takeaways is knowing what your friends bring to the table, whether socially or in terms of your creative work, and leaning into that.

Yeah, absolutely. And it’s so funny—I don’t believe New York is somehow better at creating creative opportunities, but I’ve had to go up for work a couple of times over the last few months, and there are images and moments that spark things that happen very much in public that I don’t encounter in other places.

I was walking behind these two au pairs, and they were pushing strollers and texting furiously and navigating the sidewalk without looking up. I eventually got around them, and there were no babies in the strollers. And I was like, “What is this?” I think just allowing yourself to be confused and distracted is really crucial. And it’s harder to get that when you know exactly how things will go, when you’re going to the same space where nothing really happens.

Can you say more about confusion being valuable?

I was afraid of confusion and not knowing for a really long time. Whenever I do plays and TV, I do a lot of research. But the thing I always had to break myself away from was writing book reports, because eventually, you have to create something with a life of its own.

I feel like confusion is that sensation of getting lost in a foreign city or getting lost in your own city. I need to get lost in my own life because I have a more heightened awareness of the things going on around me, and I lose some of the security blankets I might otherwise cling to. And that opens this conduit through which creativity can flow better. Maybe that sounds esoteric or like I’m Jodie Foster in Contact, but that’s the way I feel.

I think that some confusion is structural or dramaturgical, and that’s very frustrating. There’s some confusion that’s like, “I don’t know what’s going to happen next in this scenario, in this relationship. I don’t know which way to turn on this path.” That reminds my brain, at least, that anything is possible. And then I can put that back in my work.

I want to rewind to something I was hoping to ask earlier. When you realize you’re spending too much time with one of your forms of writing over the others, how do you strike a balance?

I like to keep a lot of projects going at the same time, and I’m very fortunate that people want to work with me on different projects. But even still, why do I have two newsletters? That’s deranged behavior. I don’t know how to modulate or switch gears other than, when one writing form starts to require too much attention, I try to move it to a new phase and get it off my plate so I can get back to equilibrium.

How did you get into all of these types of writing? What made you want to balance so many types of writing?

A lot of it is just saying yes to opportunities. I started off wanting to be a novelist, and I do have a novel [Kings of B’more] that’s coming out in May. But I didn’t know how to go about it. I was also a very dramatic person, and I loved theater. My love of novels and my love of theater led me into playwriting.

To circle back to what we were saying before, a lot of my motivation for exploring different avenues and writing forms is confusion. I was confused about how to [have] a career as a novelist. I was confused about how to have a career as a playwright, and so I didn’t do those things. But I really felt this desire to write, so I started blogging. And then, I thought, “Maybe I’ll turn this blog into a book.” And then I asked a friend of mine who’s an agent, “Should I self-publish?” And he very bluntly said to me, “Who would read it? You don’t have an audience.” He was like, “You need to get some clippings,” so I started writing concert reviews for Philadelphia Magazine.

It’s such a circuitous path. Anytime somebody invites me to talk at a high school, I’m like, “Oh, these poor kids.” I just said yes to things that paid me a little bit of money, and in retrospect, it really looks like I had a plan, and I did not. Even now, do I have a plan? No. My manager will say, “What do you want to do next year?” And I’m like, “I don’t know.” That’s terrifying, because I’d like to know how I’m going to pay my mortgage next year. But it’s also the only way I know how to create. I need to figure out what questions I have creatively. And then I need to figure out how to pursue them. Sometimes, that process is reversed, and somebody says, “Hey, do you want to explore this?” And then, in the middle of the exploration, I’m like, “Oh, this is actually a creative question that I had.”

Since we’ve been talking about the many things you do, are there certain days or times that you devote to one art form or when you find yourself doing your best creative work?

Unfortunately, my process is so chaotic. It’s frustrating. I think a lot of my days are dictated by the calendar. With TV, there’s a lot of meetings. For a typical day, I’ll have a meeting at noon and one at 2:00 or one at 6:00. So then I’m trying to thread all my other things in between. It’s meetings and then deadlines. I have these two newsletters I send out, and they go out a total of three times a week. So it’s also like, depending on the day, do I need to write one of the newsletters?

When I left my job at Elle, I carved out a month to write my young adult novel. That was the first time I was ever able to say, “Every day is devoted to this project.” I’d wake up in the morning, read a young adult novel, and then I’d have lunch, and then I’d do some plotting on my novel, and then maybe I’d read another novel at bedtime. I did that for a month.

About midway through, I started writing more and reading less. It was incredibly productive. … I wrote most of the novel that month, and I really hunger for that. I worry that putting too many things on my plate with hard deadlines or a need to always be cultivated runs into that. I’m trying to write my newsletter in advance so I can push it off a couple of weeks, close out my calendar, and try to put blocks of nothing in my schedule so I can fill it with the deep work and exploration that’s really crucial.

This all makes me wonder, is burnout ever a thing that feels like it could be coming your way? And in moments when it does, how do you approach that?

I really worry about it. I feel like I’m burnt out right now. I don’t have much in the tank. It’s emotional, it’s where we are in the world. It’s also like, my personal life has gotten very complicated this year. And you can only do so much.

I try and structure release valves. Even just going up to New York, it’s really useful in terms of resetting, giving myself more, filling the tank back up, seeing a show. It’s really important to me. So is just stepping away. I was feeling burnt out at Elle. It wasn’t anybody’s fault. Everybody was really supportive, but I was writing a humor column in the pandemic, at the end of the Trump presidency. I ran out of ways to be funny in that context. That was really scary to me because I was like, “Well, this is your job. You don’t have something else lined up. What do you think you’re going to do?”

I was fortunate that I had this book deal, so I was able to be like, “Okay, well, I can figure it out.” And I was fortunate that the TV industry pivoted to writing over Zoom because I was able to keep working in that industry.

I booked myself this inexpensive Airbnb in Boulder because I have a friend who lives in Denver. I was like, “I’ll go out to Boulder. I’ll spend the week working on a book, and then I’ll hang out in Denver with my friend.” And then I didn’t do any work on the book. I came back feeling less burnt out, but not really. I’m like, “Well, I don’t know how to escape my life.” So that’s the question for next year. I’m also going to be thinking a lot about community and I’m really hungry for that. I wonder how we can keep redefining what community is and how we reach each other in ways that feel meaningful as opposed to draining. That’s something I’m really interested in.