September 1, 2017 - Ben Sinclair is the co-creator of the critically-acclaimed HBO show High Maintenance. He has appeared as an actor in a handful of TV and film roles. He also knows how to lasso. Here, he talks about the importance of finding a good collaborator, why it's hard working alone, and the complications of making a TV show: "It's just constant decision making and the decision fatigue that you have to get over... It's just like everything is happening at once. And more than anything, it's just like trying to keep up."

As told to Mark Sussman, 2023 words.

Tags: Writing, Acting, Television, Collaboration, Anxiety, Process.

Ben Sinclair on second guessing yourself

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You’re just about finished shooting the new season of High Maintenance, so what are you doing now?

These days are spent securing rights for music or making notes on one thing while I’m working on something else. Right now, I’m doing this three prong thing, working with other people and changing gears is like… men are not good at multitasking.

How are you dealing with that particular challenge?

Last year, I kind of got into it, and I saw that you just have to become a better communicator. And then, sometimes the person doesn’t get you. I would rather work with somebody who just kinda gets what I’m saying with me barely having to say it or go into it. So, I end up working with people who are born the same year that I am, or near the same year that I am.

Just so you have a set of common references?

Yeah, kind of! [Laughs] “Remember that scene in Romancing the Stone where they were going down the mudslide?” Which they do. I have this other editor who was born in 1984, maybe we’re 10 days apart, birthday-wise. We know all the same references. And especially when you’re talking about cinema references, I want it to be like this or that, it’s really helpful. I work better bouncing off of people. I’m not good at solo.

Before the HBO show, when you were making High Maintenance as a web series, it was just you and Katja [Blichfeld, High Maintenance co-creator and co-executive producer] working together. It seems like working with one other equal collaborator would be “less solo” than working with three or four other people who report to you.

Well, I think writing has always been the hardest part, because it’s the most solo of all of the activities. Editing is kind of solo, but you have the voices and faces of other people, even if they’re just on film. They’re around you and you can react to an assembly that you put together. Writing is completely pulling things out of thin air and then inventing conversation and situation and structure. That part is the most lonely and probably the one I’m most averse to. Working with Katja, we were so overlapped and codependent. It felt like we were solo, but we were solo.

Like the two of you were doing something alone together?

Yes, exactly. And there was talk in the space. It seems like as I keep going, if I have an idea, I need to actually say it out loud. If I make an edit, like today, I wanted to show it to somebody, but there were other people working on other stuff and other people whose job it wasn’t to tell me, “Yes, use that” or, “Yes, use this.” I do that with the editors, but at the end of the day, it’s my decision or the editors. And with Katja, it was and it still is, what we agree on. So, High Maintenance as a show is all of the decisions that her and I agree on.

Is that how you define it?

Yeah, that’s what it is. It’s the intersection between her and me, at its best. So, she’s been away for vacation this past week, and I’ve been making a lot of the calls because of the time difference, and it’s a much different process. I really like working with others. And I think film is pretty collaborative in general. I would love to direct somebody else’s stuff.


Because [High Maintenance] is all I’ve done in terms of directing. I’ve only directed something that I’ve written. I have a lot to learn, and I think I’m in a learning phase right now.

I’m the youngest of four, and I’m really much more used to having other people call the shots. It’s relaxing to not feel like it all rests on you. Or at the end of the day, that you’re the final decision. Having the final decision seems like it would be cool and liberating, but often times, you’re like, “Well, I actually don’t really know the answer, so I’m gonna say my feeling is this answer, and I hope it all works out.” I second guess a lot. Making every decision and second guessing every decision is really tough. I’ll say, “Yes!” really enthusiastically, and then I’ll call somebody 12 hours later, and I’ll be like, “Oh fuck, we really fucked it up.”

How much of that is integrated into your process? The knowledge that eventually you’re going to second guess yourself?

We have a very long and luxurious post process for this season, with the knowledge that we’re going to change it all or that we need time to marinate so that we can change it all. And as we keep going, we keep almost doubling our workload, our episode load. When we started out, we’d do three episodes at a time, then we shot six at a time, then we shot six with two stories at a time, and now it’s ten with two-to-three stories at a time.

That’s insane.

Yeah. Making a TV show is hard. Now I’m finding out from other showrunners and people who know showrunners that when you do this, this all you do. There’s nothing to do with your life. It seems overwhelming at times. I can only imagine how Tina Fey and Robert Carlock felt making their 24 episodes of TV. And they were all so funny. And then, having to do that once a year. It’s just a lot of work.

It’s just constant decision making and the decision fatigue that you have to get over. Every decision that has to be made comes through me and Katja. So you’ll be looking at the script that you need to direct today while you’re getting texts from the costume designer with three choices for the costumes that the characters are wearing for the next scene because we couldn’t get the actors in until the morning of. And then, the assistant director is talking to you about tomorrow’s schedule. It’s just like everything is happening at once. And more than anything, it’s just like trying to keep up.

I totally understand what you’re saying about decision fatigue, but didn’t you have to make the same decisions when you were working on the web series?

Yeah, but it wasn’t all shoved within a seven week period. It was spread out. And we prepped for a week and we were shooting over two days or a three-day weekend and editing for the next three weeks. We couldn’t wait to make decisions. Every time we got a chance to make decisions, it was a true pleasure. But, to be on a decision conveyor belt and strapped into a chair and just fed one after the other, it’s fucking tiring, man. Because you don’t know. You don’t know the fucking right answer to those questions, except something has to go in front of the camera. Every time somebody smokes pot, they’re like, “What kind of pipe do you want?” And then, they roll out a thing of 20 pipes. I’m like, “Are you kidding me?” Every time. “So, we gotta talk about pipes for this scene.” [Laughs]

So what’s the release? What makes the fatigue worthwhile?

I got an Instagram message today from somebody who said that they were struggling with their cross dressing and then their therapist said, “Watch the ‘Rachel’ episode.” And it changed them. I was like, “Oh, cool. That’s the one that actually had an effect.” And I wish we did that for almost every episode. And I immediately go to “I wish, I wish, I wish.” But for a brief second, I was like, “Oh, yes.” I’m still trying to figure out what I get out of this, to be honest. It’s certainly not what I thought I was gonna get. This year, especially because of personal issues, I’ve felt very tortured. But I felt tortured last year. And if I think about it, I felt tortured every other year before that.

So many episodes are built around crises, but ordinary sorts of crises that most people have either experienced or witnessed. Where did your sense of what constitutes a crisis come about?

I had a two or three year infatuation with Chekhov. I just really was all about Chekhov in college for a little while. In all of his work, the smallest moments are the biggest moments. The most happens in the small, trivial, mundane things. So, that’s my smart answer. My other answer, my real answer, is I’m a drama queen. I just like it. Katja and I had many years of complaining. Just about everything. Life is so sweet. And I think it’s so funny that life is sweet and there’s still stuff to complain about. That’s the kind of humor I like. I’ll make it sweet, sweet, sweet, with a cynical note at the end, or cynical, cynical, cynical, with a sweet note at the end.

You think that’s the general sort of temperamental pattern?

Yeah, it vacillates between really heartfelt and “everyone’s a piece of shit, but not really.” I think that there is a decency that comes from both [Katja and I], but more her. Over the years, we really bled into each, and we became these kinda spiritual, kinda complain-y people who saw the best in people but also wouldn’t go on a road trip with anyone.

There’s a lot of complaining, but [the show is] a wonderful form of self expression and, at the end of the day, I have a platform. I won’t have a platform forever. I might not have a platform beyond this year, so I’m gonna use it. I’m gonna use it to work some shit out. And I’m gonna create loose metaphors or tight metaphors or live through [characters’] experiences, so that I can feel understood. I guess that’s why I do this, is to feel understood.

Every episode of HBO Season One is about a person or an animal trying to get out of a relationship that they’re currently in and wishing they were in a different situation. And after that, Katja and I chose to go our separate ways, romantically. So, that whole season is a pressure cooker for that situation, with both of us feeling like, “Man, I got everything. I’m fine. But, I just gotta get out. This is just not working for me. And there’s something more that I want.” Clearly, and if you look back, it really is every single episode.

I think since the election, everyone’s like, “I’m making a change.” So many changes happening this year, from all sorts of people. They’re getting divorced or having babies or changing a job or moving. It’s a big year of that. Hopefully, we’re tapping into that.

Do you think recognizing that feeling has to do with your relationship to the people you work with?

Yes, yes, yes, a thousand percent. We’ve all had to make changes, top down. It’s a different show because change happens. To be the same show, we would all have to be fucking robots. Like living in this city and and making a show that changes the way some strangers treat me has changed me. I’m different now because of all of that. That is one of the reasons why I feel different being in New York City now.

I just want to catch a cool, good vibe. The new season starts in a place of misery because we were writing during the inauguration. We were writing in the worst wintery, shitty, post-divorce time. It was awful. I was really hoping that this show could be an antidote for all of those bad feelings. I didn’t want to focus on the bad feelings.

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