December 11, 2018 -

As told to Yasi Salek, 3153 words.

Tags: Comedy, Beginnings, Inspiration, Process, Success.

On what it means to work hard

Comic and writer Jake Weisman on what makes comedy the perfect outlet, creating a television show, and self-loathing as creative fuel.

What was the first creative practice or thing that you got into? I assume it wasn’t stand-up.

No. Stand-up was very far from anything I thought I would ever do with my life when I was a kid. Mainly my love of creativity was based in reading books. I loved reading so much as a kid. It was such a gift, and I just thought, “I have to be a writer…I have to write books because it’s the best thing going.” I did love movies and I loved TV, a little less but I still loved it. But books, I was always reading all the time. Then when I was 10 I announced, “I’m gonna write something that’ll be in the New Yorker.” Because I was 10 and I thought that was important. Maybe I was 13, I don’t remember. Somewhere in that age range. I loved reading so much, and that was my first-ever goal. And I kinda failed at it.

Well, you’re technically a writer.

I feel like if you’re creative, you’re often only looking at what you’re not. You’re not appreciative of what you are. I’m so thankful to be a writer, and that I get health insurance from it, which is so much luckier than so many better writers. In terms of writing, fiction is not what I ended up doing, and I find those people to be the most amazing people because I can’t do it.

Did you pursue writing fiction at all? Did you study it in college?

Yeah. I went to school because I thought the school had, from what I read and what I’d seen, a good creative writing program. Vanderbilt. They had a great English department. I studied fiction writing and I wasn’t very good at it. There were several reasons why, I think. First of all, I don’t think I have the natural grace of my favorite fiction writers. I think I can be entertaining, but it’s not necessarily graceful, or what I respect of fiction writing. Actually, what I learned through stand-up was that I didn’t work hard enough at it. In college, I didn’t understand the intensity and passion and focus you have to have to create something even mediocre.

Stand-up allowed me to have the immediate gratification of a negative or positive response, and then to keep going. Whereas with fiction, I just felt like I wanted it to be good right away. I was also 18, and much more immature than I am now. I just wasn’t ready for it. I could write entertaining things, but nothing that anyone really liked that much. It was more a little poppy and fun, but it wasn’t what I think counts as good fiction.

You were probably also a smart kid, and when you’re a smart kid, when you try something new, you want to be really good at it right away.

Yeah, you don’t understand it. I wish schools taught you the truth, which was that it doesn’t matter how smart you are. The people who succeed because of their brilliance are outliers. Most people who succeed are either brilliant and have as good a work ethic as they have an IQ, or they’re just people who are almost a little psychotic in how hard they work. You’re really just beating your head against the wall constantly—maybe even literally—until you achieve what you want. I didn’t understand that at all until I reached my mid-20s and was extremely depressed and scared and understood how hard I had to work.

After college is when you decided to start doing stand-up?

No, not right away. In the last few years of school, I randomly took a filmmaking class, just for fun because I had always loved movies and I was curious about it. Immediately I realized, “Oh, this is much more attuned to how I think.” It made more sense to me, innately. I kind of decided to abandon fiction writing and just go out to LA and see what happened. I had a few cousins who worked in the industry who said they could probably get me some PA jobs. I had never really written a screenplay or anything. All I had written was some shorts that I had to make in my classes. I just drove out here vaguely wanting to “write” or “direct” or “make it,” whatever the hell that meant.

I started working PA jobs on set and in the office, and assistant jobs, and working as a post-production assistant. Never writing. I would write five pages of something and would throw it away because I was too scared for anyone to tell me how bad I was. I still was in that illusion that genius just happens. So I would not really do anything for years, and I was really panicking, and then at 26, I had a few friends who just happened to do stand-up. It was the last thing from my mind, I never thought of myself as particularly funny, and I had definitely lost confidence in my intelligence at that point. But stand-up was immediately such a helpful vessel to get me writing all the time. I could always get a response to what I was writing, right away. I assumed that I would just do it for six months and stop and then eventually write screenplays, but I ended up just doing standup all the time.

I needed that confidence of learning how to rehash ideas into something that was solid, but it was all based in failure that I turned into comedy. Just complete failure and devastation at myself for not accomplishing what I always felt I should.

It’s really interesting that you say that, because I think that that’s a thing to be grateful for. I learned later in life that failures—and avenues that were closed off to me that I really lamented when I was younger—were all because I had to get to the place that I was supposed to go, and it wasn’t supposed to be these other places.

Yeah, absolutely. Failure, as long as you don’t turn to heroin, is one of the best things for you, if you can understand that it’s just helping you. But it’s very hard to get past the ego and understand that, and there is this myth through so much media that, “Oh, this genius just happened,” or, “Look at this amazing person who did this stuff at age 21.” Some people are just amazing, but also, some of these people don’t know how to talk to human beings. They’re completely deficient in many other parts of their lives, and some people just are crazy and decided at age 12 that they knew what they wanted to do, and just worked at it kind of almost naively, and now they’ve been doing it for 10 years by the time they’re 22.

And they might not be happy—they might wish they could do something else, but it’s too late. It’s cemented.

Nobody’s happy. Yeah, nobody is happy. I think it takes a while to learn that, and once you get into your 20s and 30s you realize that you have your whole life to accomplish these things, and it’s fine. It should take you a while. That means it’s good.

Had you ever performed before in any fashion that made you think, “Oh, let me go and perform in front of people?”

Ostensibly, no. It definitely felt like jumping out of an airplane. The thing is, if you tell yourself you’re just gonna do stand-up a few times, it’s like a funny story at a dinner party. I’ve jumped out of an airplane before, that was just to say I did it. I ran a marathon once just to say I did it, and to see if I could.

Stand-up was similar… but it was such a transformative experience, and I’ve heard other people talk about their first few times on stage almost spiritually, where they’re like, “It changed me and what I wanted.” I think it was similar, where it was like, “Oh, this feels like the thing I should have always been doing.” I think I was always too scared to admit to myself that I wanted that kind of attention. With stand-up, I could control the environment and perform and have it the way I wanted it, and I never knew or admitted to myself that’s what I wanted… It just felt like something I had to chase and I kind of dropped everything in my life to pursue it.

Now you have a TV show. And it’s about soul-sucking day jobs, amongst other things. Did you have that kind of experience in your work life before you were able to make a living from your comedy?

I haven’t worked that much in corporate America, but Corporate was just sort of the environment we thought would be a hook. If you’re not doing what you love for a living and you don’t have a kid to support, it does feel horrible to be at almost any job. Rugged capitalism is so brutal and so unforgiving, and fine, that’s the system we have. I’m not trying to change it, there’s no way anyone could change it really, but it’s so horrible and it’s really funny, I guess, to us.

Most shows about workplaces showcase the jobs as kinda crappy, but you know what, your friends at work really help you get you through the day and they’re really silly and goofy. I’ve never had a work experience like that. I’m sure that exists somewhere, but most of my work experiences are people who are depressed and boring, and completely shut down by what life did to them. They feel as if life happened to them and they can’t figure out how they got there, and then they have a nice apartment and they have to keep affording it. They don’t want to live lesser than their means, or they don’t want to live a lesser lifestyle than they’re used to now, and they just kinda get caught, and all of a sudden they’re 45 and they’re just like, “What the fuck happened to me?”

So, I think we wanted to make a show that was more honest about work, because it always feels like most entertainment is this fantastical escape from reality. I want my comedy to cut me a little bit because I want to feel seen. We felt like if we could make something accurate, that people would feel seen or that their lives weren’t necessarily wasted, because they’d be like, “Oh, this is a common experience.” So in a way, I know it hurts a little bit, but even if a laugh hurts, it feels productive.

We wanted to transmit that feeling that I think a lot of people feel, which is, “Why am I wasting my life doing this just for money?” And, of course, you have to survive, and it’s a privilege to not just survive, but regardless, that is the feeling that a lot of people have and we wanted to accurately reflect that. Just the feeling of being at any job that you don’t want to have and how horrible it is and how stupid you feel. That’s what we were trying to affect.

How did you personally stay creative while dealing with that?

It took me a while to figure it out. The jobs I had up until I started comedy were pretty intense. They were PA jobs, or post-production coordinator, supervisor jobs. So then at 26 when I started comedy, and I realized I was gonna pursue it, I quit for a job in a chandelier store where I knew I’d be able to just get the work done and then be able to write, or be creative, and have time to think. I decided to leave the industry behind.

I think a lot of people make the mistake of working within the film industry, and giving all of their energy to their job. And then at night, they’re so depressed by the fact that… it’s like an arm’s length away, you wanna be in that writer’s room but you can’t. So you PA, and then work 16 hours a day and eat too much at the craft service table and you’re depressed at night so you drink, or you drink on the weekends just to get rid of the fact that you’re not doing what you want to do.

So I decided to leave the industry to find my way back into it. It was a gamble, but I was like, “Well, if I have time to write and I could perform and then figure out how to write, I’ll probably know someone who eventually, if I’m good enough, will let me back into the industry in a place I actually wanna be in.” And it worked.

The other recommendation I have is, if you’re working in entertainment, don’t necessarily work in that industry. Just work in a field or a job where it doesn’t control your brain so you can just write, or write on breaks, or fake write, or do whatever you can. Don’t let them have control over your energy, and figure out a way to write on your off time. You just have to believe it’ll work out.

You just have to understand that if you want to be creative for a living, the world is working against you, because unfortunately the world doesn’t need art to function. So you have to force it, and you have to do it by working insanely hard and living kinda crazily for a while in order to force the issue. You have to make yourself needed, and most people don’t really respect art that much. So you have to be really tired and you have to kinda hate everything, and just force it to happen.

What do you do when you have writer’s block or you’re feeling creatively stuck? Do you have methods that are tried and true?

I hate myself deeply. Luckily with a lot of things I do, I often collaborate. Partially because I’m insecure. I don’t collaborate on stand-up. Except sometimes, we just tag each other in shows because you get together and write with them, but stand-up is not something I collaborate on because it’s a solo act. With most things that are creative for me, I’m working with other people, and I kind of feel like that’s what stops writer’s block. Because if there are two or three people there, who are now doing this for a living, who need to keep doing it for a living, eventually, you’re just gonna have to figure something out.

Writer’s block, I know it’s real for some people, but I’ve also read a lot of people who were like, “It’s bullshit.” I’m kind of in between. Right now we’re about to finish locking Season 2. I finished Season 2 and I’m like, “Uh oh, what am I gonna write next? I have no new ideas.” But I know something will come because it has to or I won’t survive. So even if it’s not the best thing I write, I also want to make money, and I’ll just write bullshit if I have to. I don’t think that’s what’ll happen, I think it’ll be great. But I think—and this is really fucked up—but I have such an intense self-hatred and such a dissatisfaction with myself, if I’m not producing enough things… that eventually something just comes.

A lot of it is I’m never that proud of what I’ve done. I always feel like I could have done more. I always kind of feel like I’ve wasted so much time. So I feel like once that self-hatred and dissatisfaction seeps into my existence, I can think about other things that frustrate me. I get mad at everything, and then eventually when you’re mad at everything, you can write. You’re like, “Oh, I wanna write about why that sucks.”

This thing I’m mad at.

I think it’s based in dissatisfaction of myself, but then I project that onto other people and things, and then I can write. I’m too scared to not produce stuff right now, and I don’t have a privileged enough career yet to not be producing all the time. So my answer right now is I just want to be successful so I can feel safe, [so] I don’t experience writer’s block very often. I just keep collaborating and keep writing and keep thinking and keep not having enough sleep and keep feeling this anxiety that I’m never gonna be able to do this again. So I pay a price, but it’s worth it, essentially.

You mentioned you want to be successful. What does that mean to you?

What it means to be successful is to be able to make a living, and living comfortably, off my creativity. I don’t have a number in mind, it literally just means to be able to essentially pay my rent by being creative and, ideally, creative in the way that I explicitly want to be. Sometimes you have to just do dumb stuff or write stupid projects or whatever for the money, but my image of success is [that] they’re gonna be like, “Write what you want. Make what you want. You’re good enough so we trust you.” But on the lowest level, it’s to be writing for a living.

What about failure?

Failure is not working hard enough. It’s like… if what I’m writing isn’t good enough, oh well. But if I’m not working hard enough-

Then only you are to blame.

Yeah, and obviously working hard is a skill. I feel like I’m lucky that I work hard. Not everyone can work hard. If they could, they would. But I’m very lucky that I’m motivated to work hard and if I ever lost that, I would feel like I truly failed. Right now, when I think about it, if in my bones I know that I’m not working hard enough, I would feel like I’m failing myself. I would feel the most shame about it.

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