On making people laugh without losing your mind

What is the landscape of your creative life at the moment?

Well, stand up will always be my first love and it’s the thing that I tried not to do. I tried to be a regular grownup and go to an office for years, and then I finally started doing stand up and I was like, “Uh oh, this is here to stay.” When you do stand up, you do a lot of writing. You are a writer, and then you have these ideas for shows that maybe don’t work for stand up. I do have a pilot, I have two podcasts that are both on extended hiatus right now, but I’ve always been that person who has to have many things going at once. I have really bad ADD, so I like to make sure there is always something to do. But I say a lot that if I could have quit stand up, I would have quit by now. I just can’t stop doing it. But I want to. I just can’t, I’m sorry.

Do you have a day job?

I do. It’s remote and it’s freelance now. I actually moved to New York because my job moved me. I wasn’t planning to go to New York to “make it” at all. I wanted to stay in San Francisco and keep doing it there until I figured out what was next, but my job was basically like, “You can either keep your job and move to New York or you can stay in San Francisco and take your chances.” Which was basically like saying, “You won’t have a job.” As much as I would have enjoyed being unemployed in San Francisco, I was kind of like, “I can’t as a comedian say no to somebody paying for me to move to New York.”

I think in terms of managing my day job versus my artistic career, I can say that having a freelance day job has been so helpful to me just because I can set my own schedule. I belong to a workspace, so when I need to do something productive and really get plugged in and have nobody bothering me, I’ll go there. There’s other people doing work there and it’s a very “we’re all doing work” vibe. I am more motivated in that environment. But I think the combination of ADD and a freelance lifestyle, it works to your advantage as a creative when you have more flexibility like this. If I was reporting to an office at 9:00 AM every day at this point, I don’t know where I would be emotionally. It’s funny, writing jobs—like working in the writer’s room on a show—are something that most stand ups try and pursue, and I haven’t really done that because I’m like, “That is an office job. That is exactly what I tried to get away from.” Not that I wouldn’t take it. I would love to be in the writer’s guild, I would totally do it.

When you moved here and you were doing comedy stuff, did you know people in the comedy world already?

I knew a couple, because I’d been doing it in San Francisco for three and a half years at that point, plus I would come to New York sometimes. I had done a couple open mics, but I was certainly not prepared to come to New York as a comedian. It was a rough landing. I had major, major self-doubt for a long time. It was helpful to know a couple of people here, for sure. I think I was actually one of the first of my class of comedians from San Francisco to get out here, and then Emily Heller moved about six months after I did and she was my roommate. Once she got here I saw what it could be like when you’re actually prepared. I was like, “Oh, well that’s not what I did.”

There’s always those people who come to New York, take it by storm, and move really quickly up the ranks, or whatever. And if you aren’t going to be that person, then I think putting in your time in New York is key, and patience is probably better than preparedness, in terms of commercial success. Also, having seen commercial success and what it can do to comedians and how difficult it is to manage, I’m kind of like, “Do I even want that?” I think maybe I just want to not make any money off this and talk about whatever I want.”

People tend to have an abstract idea of what success actually means, but the reality of that can be very different.

Yeah. Certainly when I started I was like, “I’m going to do this for three years and if I don’t make it, I’m quitting.” Because that means you’re not good. If you don’t “make it,” then you’re just not funny. And now having been on the other side of that, when people are like, “Oh, I don’t want to go to this comedy show because I’ve never heard of anybody on the bill.” I’m like, “That doesn’t mean anything. You don’t know anything about comedy.”

When you get to New York City, is the goal just to work your way up through the ranks at the clubs and then eventually to secure management? Or is it just about getting up on stage as much as possible?

A little of both, maybe. The club system can be hard to navigate, especially if you haven’t made a big name for yourself. It’s a lot of standing around and late nights hoping to get a spot, which is a hard thing to manage if you’ve also got a day job. And yes, the other goal would be to eventually get management. I would love to get management. That would be amazing. I would love to do that. Somebody just tell me what to do, you know?

So when you don’t have an agent or manager booking stuff for you, how do you figure out how and when and where to perform?

Well, I have my two shows that I produce, so those are like my anchors. One is first Tuesdays, and the other one is third Thursdays. I also have an open mic that I love that I go to once a week. And then I just try to fill things in from there. I’ve been here for long enough now that I have friends, like me, who are like, “Hey, I did your show six months ago, can I get another spot?” I’m bad at asking for new shows, but that is definitely something that somebody who is moving to New York should try and be good at. I would just say make it your business to ask for five shows a week or something. You know? I still struggle with it, and I feel like I have much more of a profile now, but I still feel weird asking. If they wanted me on their show, they would ask me, right? But it’s not true. There’s so many thousands of comedians here that you have to do the work to put your name in front of them.

Do you find that you’re always writing? How do you typically develop your material?

I’ll write things down on my phone, things that I just said to somebody. Or I’ll realize that I’m talking about something to a bunch of people and I’ll be like, “Okay, this is something that I’m thinking about enough that I probably should take it on stage and see what happens, just explore it.”

New York is great in that way. There are all these spaces where you can try things out.

Yeah. Open mics can be really torturous, but it’s interesting to see what people choose to talk about on stage, and you can get inspired from that. From the totally mundane observations, to people getting really philosophical and talking about death. That’s one reason that I really like being in New York—people talk about everything and you can see it anytime.

In regards to mainstream success, you do see a common sort of trajectory that happens to a lot of comedy people, in which big-time success dulls all their edges. Everything becomes inherently less risky.

I think it happens with artists overall. If you’re hungry, you will put forth more effort. And I also think once you get to a certain level of success, it’s harder. You can’t get that honest feedback from audiences because they know who you are and they want your approval more than you want theirs. Also, the audiences that are coming to see you already like you, so you don’t need to try as hard. Not to mention, if you have an entourage of whoever, they’re not necessarily going to be real with you either. I think big success makes it hard to trust people, and the feedback that you get isn’t always genuine. It makes me jealous sometimes that musicians can audition behind screens so that they can’t be seen. We can’t do that, obviously, because the material is so personal, but in terms of trying to get your material judged objectively, I think once you have a profile and people are coming to see you because you’re you, it gets harder. Whereas, I never have to worry about that. If I’m not funny, people are going to let me know.

I was listening to your record, Hard Pass, which is very funny. The whole idea of comedy records is fascinating to me. It seems like because of things like iTunes and digital media, it has become a fruitful world for people to make comedy records and to be more experimental with them. I feel like it allows a certain amount of freedom for people to do weird things with the format. What was that process like? Did you record your set over different nights?

It was one night, two shows. One was at 7:00, the second one was at 9:30. It was at The Duplex in the West Village, which is my comedy home. I love it. I go to their open mic every Wednesday. I recorded it at the cabaret theater upstairs. And the first show, there were people who came up from DC, which is where I’m from, so people who’d never seen me perform were like, “We’re going to be there. We’re going to come support you.” They were so excited to be there, that first audience, that I didn’t use any of the audio for the first 15 minutes because it was not about me being funny. They were laughing because it was me. That was interesting to realize, because after the shows I was like, “Oh, the first one’s definitely the best one. I’m probably using like 80% of that show. And when I listened to them, I was like, “No, wow I was wrong.”

The experience of listening back to your material in that way, listening to your own voice on a recording and shaping it…

Terrific. [laughs]

I mean, I can’t imagine what that would be like.

Well, it’s one of the basic tools in a comic’s toolbox—listen to your sets. It doesn’t matter. You hate the sound of your own voice? Doesn’t matter. You’re just going to have to suck it up and do it. It really helps. And I also had two podcasts like I mentioned, so I’m pretty used to the sound of my own voice. So that part didn’t bother me, but I definitely have perfectionist tendencies, so there are still, even now, a couple of things on there where I’m like, “Oh, I don’t like this.” But overall, I’m very happy with it and proud of how it came out. But yeah, actually listening back was not bad because I was really happy with the show, relatively speaking. Listening to a bad set is really, really… well, I have nightmares about it.

It’s a fascinating time for comedy. I was just reading the Todd Phillips comments about how political correctness has essentially made it so that people can’t do comedy anymore…

I mean, it’s made it so that he can’t make comedy anymore. But yeah, it is preposterous. There’s this clip of George Carlin that’s been circulating lately where he’s talking about Andrew Dice Clay. He’s on Larry King and he’s talking about Andrew Dice Clay, and he says, “I don’t think Andrew is racist, but he is playing to a part of the population that is threatened by the success of non-white male groups.” I’m doing a terrible job paraphrasing, but it’s a great clip. I mean, George Carlin, he’s it for me. And it’s really validating to see something like that from, I think it was 30 years ago. It kind of sums up what I think is true about a certain kind of bad comedy, which just punches down at people.

Do you find that the culture of comedy has changed a lot in the time that you’ve been doing it? I saw a comedy show happening here in Brooklyn the other night and it was the most diverse lineup I’d ever seen. I was thinking it would be nice if that show itself was a kind of mini barometer for how that world is also changing.

I think that is where the true diversity is—small places, different kinds of venues—because most clubs are still clinging to that conventional wisdom. I saw something from the Comedy Store, and this might’ve been in a private Facebook group or something, but they said something like, “Oh, we just can’t find any women comics to perform on our shows.” And that just isn’t true. I’ve been to LA not even that many times, and even I can name a bunch of comics who could do their fucking nightly shows. It’s just crazy. I think it’s like the alternative comedy scene maybe has more of a business imperative and an opportunity to showcase a diversity of people. The people that you want to see in the audience are the people that you should have on your show, you know? So it’s not about being somehow unfair to the pool of available comics—who are whatever percentage of mostly white dudes—it’s about putting different kinds of stories and voices out there. I don’t know why you wouldn’t want a diverse lineup anyway, right? It makes the show so much more interesting. But I don’t run a club.

Do other comics ever ask you for advice? It’s not exactly an easy path to try and navigate—there’s not exactly an A to B to C path for being a successful comic.

Yeah, it’s really just hard work and luck. And even for me, having done it for this long—12 years, basically—I don’t want to say that I have nothing to show for it, because I think I have a lot to show for it, but in terms of what people who are outside the artistic community view as success… should I have accomplished more? That is hard to come to terms with sometimes. So I feel like putting out this album has been great because I feel fulfilled and like I’m doing something right… and I haven’t been wasting my time in basements all these years. [laughs]

Of course! It must be very satisfying to have this document of all this material.

Yeah, I’m totally like, “Go ahead, judge it. It’s good. Thanks.” I am really, really proud of it. I’m kind of like, “Do I have another record in me? Am I done now?” When I put it out, I was like, “Okay, now I did this. I can quit. I can at least feel like I did this and now I’m done.” But I don’t think I can quit. I don’t think it’s going to happen.

Are there things that, for you, serve as evergreen sources of inspiration? Things that you come back to over and over again when you need to be reminded about what is funny or how to be funny?

There are a lot of comics I love, of course, but I can’t think of anything totally specific that I return to again and again. Oh, but do you remember the movie Punchline, with Tom Hanks and Sally Field? There’s a scene in that movie where he has a complete breakdown, a total dark night of the soul, because no one has discovered him yet and he’s been doing comedy for 18 months. And it’s just like, “What?” It gives me a lot of perspective because it’s just like, you have got to be fucking kidding me, dude. Like, you might never get anywhere!

Since the election and with everything going on, I actually take comfort in the idea that none of this actually matters. Death waits for all of us. So if I can just have a good time and make some people laugh, then why am I trying to prove myself to people who don’t necessarily even care? My new thing is, “Am I enjoying myself? Am I not fucking myself for the future?” Then I’m doing okay. It’s like, “Relax. Why are you anxious? Who cares?”</span>

That’s a good way of keeping things in perspective.

I also have a creative coach. I should’ve said that before, actually, in regards to goal setting. I did a class last January and I put an album as one of my goals. It wasn’t my main goal, but I put it down. I don’t think I would have accomplished it if I hadn’t taken this class. It was mostly about being accountable to somebody, and because there were other people in the class, I was accountable to multiple people and also just inspired because everybody was there trying to accomplish their goals. So having somebody to share the struggle with sounds fucking cheesy, but it did help me. I’d recommend it.

That makes sense. Doing comedy—particularly stand up—is actually a very solitary pursuit in many ways.

Yeah, it’s a very lone-wolf thing to do. And I think it’s hard for comics who transition to being a writer on a show, or even just being on a team with anybody, because what we do is so independent. We need that audience. We can’t do it without the audience, but deciding what’s going to be said and how it’s going to be said… it’s all up to you.